SUSTAINABLE FUEL COMPOSITIONS AND METHODS OF MAKING THE SAME

Description

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the benefit of priority to U.S. Provisional Patent Ser. No. 63/721,929 entitled “SUSTAINABLE FUEL COMPOSITIONS AND METHODS OF MAKING THE SAME,” filed Nov. 18, 2024, the disclosure of which is incorporated herein in its entirety by reference.

BACKGROUND

In aviation, a major pathway for producing Sustainable Aviation Fuel (SAF) is through the Hydroprocessed Esters and Fatty Acids (HEFA) process, which relies on the use of, for example, the sourcing of vegetable oils, animal fats, and waste oils. The United States is predicted to see a 1,400% increase in sustainable aviation fuel production capacity in 2024 and the global SAF market is projected to grow from $1.1 billion in 2023 to $16.8 billion by 2030.

SUMMARY

Provided herein, in some embodiments, is a method of preparing a sustainable fuel, the method comprising:

• • (a) providing a composition, wherein the composition comprises:
    • one or more substituted or unsubstituted lactones, one or more lipids represented by a structure of Formula (I), or a combination thereof;

• • • wherein,
      • R¹ is hydrogen (H) or an acyl group (COCH₃);
      • R² is 1 to 10 O-acylated 3,5-dihydroxydecanoate or 3,5-dihydroxydodecanoate groups;
      • R³ is L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; and
      • R⁴ is C₅-C₇ alkyl;
  • (b) processing the composition to produce a crude fuel mixture; and
  • (c) purifying the crude fuel mixture to provide the sustainable fuel.

In some embodiments, provided herein is an aviation fuel, comprising:

• • (a) C₈-C₁₆ deoxygenated hydrocarbons, comprising:
    • (i) C₈-C₁₀ deoxygenated hydrocarbons in an amount of at least 70 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons;
    • (ii) C₁₁-C₁₃ deoxygenated hydrocarbons in an amount of at most 15 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons;
    • (iii) C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of at most 15 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons; and
  • (b) one or more of sulfur, nitrogen, phosphorus, potassium, magnesium, calcium, sodium, iron, aluminum, and silicon.

In some embodiments, provided herein is a diesel fuel, comprising:

• • (a) C₁₆-C₂₂ deoxygenated hydrocarbons, comprising:
    • (i) C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of at least 40 wt % relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons;
    • (ii) C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of at least 15 wt % relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons;
    • (iii) C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of at least 15 wt % relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons; and
  • (c) one or more of sulfur, nitrogen, phosphorus, potassium, magnesium, calcium, sodium, iron, aluminum, and silicon.

BRIEF DESCRIPTION OF THE DRAWINGS

In the drawings, which are not necessarily drawn to scale, like numerals describe substantially similar components throughout the several views. Like numerals having different letter suffixes represent different instances of substantially similar components. The drawings illustrate generally, by way of example, but not by way of limitation, various embodiments discussed in the present document.

FIG. 1 shows an illustrative method for preparing sustainable fuel, such as renewable diesel (106), sustainable aviation fuel (107), and light fuel and/or naphtha (108).

FIG. 2 shows an illustrative method for preparing sustainable fuel, such as renewable diesel (211), sustainable aviation fuel (212), and light fuel and/or naphtha (213).

FIG. 3 shows the relative abundance of various lipids as described herein.

FIG. 4 shows estimated hydrocarbon mole percentages of lipids as described herein.

FIG. 5 shows simulated distillation curves as discussed in the examples.

DETAILED DESCRIPTION

Reference will now be made in detail to certain embodiments of the disclosed subject matter, examples of which are illustrated in part in the accompanying drawings. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the exemplified subject matter is not intended to limit the claims to the disclosed subject matter.

Provided herein are methods of producing sustainable fuel, including for example, sustainable aviation fuel, renewable diesel, renewable naphtha, and sustainable light fuels. One of the primary challenges with the HEFA process, a major pathway for producing SAF and renewable diesel, is the ability to secure adequate and sustainable supply of feedstocks. Feedstocks such as vegetable oils, animal fats, and waste oils need to be available in large quantities and at competitive prices to make the process economically viable. It is estimated that these conventional HEFA feedstocks can support up to about 6 billion gallons of SAF production within the US, while US aviation fuel demand is projected to be around 36 billion gallons by 2030. Additionally, fluctuations in feedstock prices can impact the cost-effectiveness of HEFA-derived fuels. Provided herein are methods of preparing sustainable fuels (e.g., SAF, renewable diesel) comprising the use of microbially-derived heavy oil (e.g., lipids described herein) that may be sustainable and comprise a low carbon intensity (CI).

The methods and compositions discussed herein address several technical challenges with existing sustainable aviation fuel (SAF) production methods. For example, feedstock supply chain issues, cost volatility, environmental impact, and processing complexity can all create challenges in SAF production. In some cases, the HEFA process faces challenges securing adequate and sustainable feedstock supplies, as vegetable oils, animal fats, and waste oils must be available in large quantities at competitive prices. Fluctuations in feedstock prices significantly impact the cost-effectiveness of HEFA-derived fuels. For some vegetable oils well-suited for SAF production, such as palm oil, cultivation can contribute to deforestation and habitat loss in ecologically sensitive regions, with detrimental carbon intensity (CI) and environmental effects that may disallow their use as HEFA feedstock in the United States. Additionally, traditional methods require extensive purification processes including deodorization, neutralization, degumming, and bleaching.

The methods and processes discussed herein address these challenges by providing feedstock materials and process features.

The feedstock materials can include microbially-derived lipids, or more specifically, use of bio-derived lipids from A. pullualans comprised of carbohydrate head groups and 2-5 C₈-C₁₆ polyester tails in an example. The feedstock materials can further include substituted lactones, for example, employment of 5-hydroxy-2-decenoic acid-8-lactone (Massoia lactone) and 3,5-dihydroxydecanoic acid-8-lactone as sustainable fuel precursors. The feedstock materials can include high-yield microbial production, such as by leveraging A. pullulans organisms capable of producing at least 50 g/L of target lipids. In an example, the feedstock composition can have specific ratios of lipids, and/or specific lactone ratios.

Process features can include simplified processing, such as methods that eliminate the need for deodorization, neutralization, degumming, or bleaching due to the clean nature of the lactone precursors, and integrated conversion process, such as direct conversion of microbially-produced lipids to lactones through saponification and thermal/acid-catalyzed lactonization. In an example, the processing conditions can include hydrotreatment, isomerization/cracking, product separation, or combinations thereof.

The methods described herein can result in beneficial SAF composition and renewable diesel. Moreover, the methods and composition here can have a lower carbon intensity, for example, sustainable fuels with a CI of less than 40 g CO₂e/MJ. The methods can have reduced agricultural impact by reducing dependence on palm oil and other problematic agricultural feedstocks; can have economic advantages by reducing costs; and can have process advantages through simplified processing.

Certain Definitions

As used herein and in the appended claims, the singular forms “a,” “and,” and “the” include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to “an agent” includes a plurality of such agents and equivalents thereof known to those skilled in the art, and so forth. When ranges are used herein for physical properties, such as molecular weight, or chemical properties, such as chemical formulae, all combinations and subcombinations of ranges and specific embodiments therein are intended to be included. The term “about” when referring to a number or a numerical range means that the number or numerical range referred to is an approximation within experimental variability (or within statistical experimental error), and thus the number or numerical range may vary between 1% and 15% of the stated number or numerical range. The term “comprising” (and related terms such as “comprise” or “comprises” or “having” or “including”) is not intended to exclude that in other certain embodiments, for example, an embodiment of any composition of matter, composition, method, or process, or the like, described herein, may “consist of” or “consist essentially of” the described features.

As used herein, the term “heavy oil,” and grammatical variants thereof, refers generally to a mixture of lipids described by Formula (I), and shown in Table 1. These lipids are generally molecules within a subclass of biosurfactant glycolipids identified as polyol lipids that can be produced by yeast-like fungi of the Aureobasidium genus. Heavy oils are amphiphilic molecules comprising a polyol head group such as mannitol, arabitol, or glycerol, attached to one or multiple O-acylated 3,5-dihydroxydecanoic acid or 3,5-dihydroxydodecanoic acid group tails. The tails may be acetylated at the hydroxyl (—OH) group. 3,5-dihydroxydecanoic acid derived heavy oils lacking the polyol head group are classified as aglycone oligo-dihydroxydecanoic acids (DDA) (formerly exophilins).

Carbon Intensity (CI), as described herein, can refer to a measure of carbon dioxide and other greenhouse gases per unit of activity (e.g., manufacture of sustainable fuel (e.g., SAF)). In some embodiments, CI is measured using the The Greenhouse gases, Regulated Emissions, and Energy use in Technologies (GREET) model, which uses chemical, feedstock, process, utility and other relevant input data related to the production of a fuel or chemical to calculate the emissions associated with that fuel or chemical and determine a CI score for that product based upon the total greenhouse gas emissions produced per unit of activity (e.g., as described at http://greet.anl.gov/). In some embodiments, CI is calculated using the R&D GREET 2024 model as described at http://greet.anl.gov/.

“Amino” refers to the —NH₂ functional group.

“Hydroxyl” refers to the —OH functional group.

“O-acylation” as used herein refers to the attachment of an acyl group (R—C═O) to an oxygen atom in a molecule such as to form an ester (R—C(═O)O—R′).

“Alkyl” refers to a straight-chain, or branched-chain saturated hydrocarbon monoradical. Examples include, but are not limited to methyl, ethyl, n-propyl, isopropyl, 2-methyl-1-propyl, 2-methyl-2-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-3-butyl, 2,2-dimethyl-1-propyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2,2-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, tert-amyl and hexyl, and longer alkyl groups, such as heptyl, octyl and the like. Whenever it appears herein, a numerical range such as “C₁-C₆ alkyl” or “C_1-6 alkyl”, means that the alkyl group may consist of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms or 6 carbon atoms, although the present definition also covers the occurrence of the term “alkyl” where no numerical range is designated. In some embodiments, the alkyl is a C_1-10 alkyl. In some embodiments, the alkyl is a C_1-6 alkyl. In some embodiments, the alkyl is a C_1-5 alkyl. In some embodiments, the alkyl is a C_1-4 alkyl. In some embodiments, the alkyl is a C_1-3 alkyl. Unless stated otherwise specifically in the specification, an alkyl group may be optionally substituted, for example, with oxo, halogen, amino, nitrile, nitro, hydroxyl, haloalkyl, alkoxy, carboxyl, carboxylate, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, and the like. In some embodiments, the alkyl is optionally substituted with oxo, halogen, —CN, —COOH, —COOMe, —OH, —OMe, —NH₂, or —NO₂. In some embodiments, the alkyl is optionally substituted with halogen, —CN, —OH, or —OMe.

The term “modification” with respect to a gene or a nucleic acid (and related terms such as “modify” or “modified”) can mean knockout, disruption, truncation, knockdown, inhibition, insertion, deletion, mutation, or substitution. It can result in an increase or enhancement in expression of the modified gene. It can result in a decrease in expression of the modified gene.

Methods of Making Sustainable Fuel Compositions

Provided herein, in some embodiments, are methods of preparing a sustainable fuel, such as a sustainable aviation fuel, renewable diesel, renewable naphtha, or sustainable light fuels. In some embodiments, provided herein is a method of preparing a sustainable fuel. In some embodiments, the sustainable fuel is sustainable aviation fuel. In some embodiments, the sustainable fuel is renewable diesel (e.g., renewable diesel fuel). In some embodiments, the sustainable fuel is renewable naphtha (e.g., renewable naphtha). In some embodiments, the sustainable fuel is light fuels (e.g., sustainable light fuels).

In some instances, the methods provided herein produce sustainable aviation fuel, wherein the sustainable aviation fuel comprises a mixture of C₈-C₁₅ hydrocarbons. In some instances, the methods provided herein produce renewable diesel, wherein the renewable diesel comprises a mixture of C₁₂-C₂₀ hydrocarbons. In some embodiments, the methods provided herein produce renewable naphtha, wherein the renewable naphtha comprises a mixture of C₄-C₁₀ hydrocarbons (e.g., comprising a mixture of C₅-C₆ hydrocarbons). In some embodiments, the methods provided herein produce sustainable light fuels, wherein the sustainable light fuels comprise a mixture of C₁-C₄ hydrocarbons.

In some embodiments, the methods herein comprise providing a composition, wherein the composition comprises one or more substituted or unsubstituted lactones, one or more lipids comprising a carbohydrate and 1 to 10 C₈-C₁₆ polyester tails, or a combination thereof.

In some embodiments, the methods comprise providing a composition comprising one or more substituted or unsubstituted lactones. In some embodiments, the lactones are saturated or unsaturated lactones. In some embodiments, the composition comprises one or more substituted or unsubstituted saturated or unsaturated lactones. In some embodiments, the composition comprises one or more substituted saturated or unsaturated lactones. In some embodiments, the composition comprises one or more saturated or unsaturated lactones substituted with one or more of C₁-C₈ alkyl and hydroxyl.

In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-8-lactone (Massoia lactone):

In some embodiments, the 5-hydroxy-2-decenoic acid-8-lactone is (R)-5,6-dihydro-6-pentyl-2H-pyran-2-one.

In some embodiments, the composition comprise 3,5-dihydroxydecanoic acid-8-lactone:

In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone. In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone at a ratio of at least 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, or 4:1. In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone at a ratio of at most 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, or 1:4. In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone at a ratio of about 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, or about 1:4. In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone at a ratio of from about 10:1 to about 1:10, from about 5:1 to about 1:5, or from about 2:1 to about 1:2.

In some embodiments, the methods comprise providing a composition comprising one or more lipids comprising a carbohydrate and 1 to 10 C₈-C₁₆ polyester tails. In some embodiments, the composition comprises one or more lipids comprising a carbohydrate substituted with between 1 to 10 C₈-C₁₆ polyester tails. In some embodiments, the composition comprises one or more lipids comprising mannitol, glycerol, or arabitol, substituted with 1 to 10 C₈-C₁₆ polyester tails. In some embodiments, the composition comprises 3,5-dihydroxydecanoyl and/or 5-hydroxy-2-decenoyl esters of arabitol or mannitol. In some embodiments, the methods comprise providing a composition comprising one or more lipids comprising 1 to 10 C₈-C₁₆ O-acylated (e.g., O-linked) polyesters without a carbohydrate headgroup. In some embodiments, the methods comprise providing a composition comprising one or more lipids comprising 1 to 10 C₈-C₁₆ O-acylated (e.g., O-linked) polyesters without a carbohydrate headgroup alone or in combination with one or more lipids comprising a carbohydrate and 1 to 10 C₈-C₁₆ polyester tails.

In some embodiments, the one or more lipids are represented by a structure of Formula (I):

In some embodiments, R¹ is hydrogen (H) or acetyl (CH₃CO). In some embodiments, R¹ is hydrogen (H) or R¹CO. In some embodiments, R¹ is C₁-C₆ alkyl. In some embodiments, R¹ is methyl. In some embodiments R¹ is hydrogen. In some embodiments, R¹ is acetyl (CH₃CO).

In some embodiments, R² is hydrogen. In some embodiments, R² is 1 to 10 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 1 to 8 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 1 to 6 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 1 to 5 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 1 to 4 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 1 to 3 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 1 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 2 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 3 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 4 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 5 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 6 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 7 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 8 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 9 O-acylated 3,5-dihydroxydecanoate. In some embodiments, R² is 10 O-acylated 3,5-dihydroxydecanoate.

In some embodiments, in R², one or more O-acylated 3,5-dihydroxydecanoate may be substituted with O-acylated 3,5-dihydroxydodecanoate.

In some embodiments, R² is 1 to 10 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 1 to 8 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 1 to 6 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 1 to 5 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 1 to 4 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 1 to 3 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 1 O-acylated 3,5-dihydroxydecanoate or 3,5-dihydroxydodecanoate. In some embodiments, R² is 2 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 3 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 4 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 5 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 6 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 7 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 8 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 9 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof. In some embodiments, R² is 10 O-acylated 3,5-dihydroxydecanoate, 3,5-dihydroxydodecanoate, or a combination thereof.

In some embodiments, R² is

In some embodiments, R² is

In some embodiments, R³ is L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol. In some embodiments, R³ is L- or D-glycerol. In some embodiments, R³ is L-glycerol. In some embodiments, R³ is D-glycerol. In some embodiments, R³ is L- or D-threitol. In some embodiments, R³ is L-threitol. In some embodiments, R³ is D-threitol. In some embodiments, R³ is L- or D-erythritol. In some embodiments, R³ is L-erythritol. In some embodiments, R³ is D-erythritol. In some embodiments, R³ is L- or D-arabitol. In some embodiments, R³ is L-arabitol. In some embodiments, R³ is D-arabitol. In some embodiments, R³ is L- or D-xylitol. In some embodiments, R³ is L-xylitol. In some embodiments, R³ is D-xylitol. In some embodiments, R³ is L- or D-ribitol. In some embodiments, R³ is L-ribitol. In some embodiments, R³ is D-ribitol. In some embodiments, R³ is L- or D-allitol. In some embodiments, R³ is L-allitol. In some embodiments, R³ is D-allitol. In some embodiments, R³ is L- or D-altritol. In some embodiments, R³ is L-altritol. In some embodiments, R³ is D-altritol. In some embodiments, R³ is L- or D-mannitol. In some embodiments, R³ is L-mannitol. In some embodiments, R³ is D-mannitol. In some embodiments, R³ is L- or D-iditol. In some embodiments, R³ is L-iditol. In some embodiments, R³ is D-iditol. In some embodiments, R³ is L- or D-gulitol. In some embodiments, R³ is L-gulitol. In some embodiments, R³ is D-gulitol. In some embodiments, R³ is L- or D-glucitol. In some embodiments, R³ is L-glucitol. In some embodiments, R³ is D-glucitol. In some embodiments, R³ is L- or D-galactitol. In some embodiments, R³ is L-galactitol. In some embodiments, R³ is D-galactitol. In some embodiments, R³ is L- or D-talitol. In some embodiments, R³ is L-talitol. In some embodiments, R³ is D-talitol. In some embodiments, R³ is 2-amino-D-mannitol. In some embodiments, R³ is 2N-acetylamino-D-mannitol. In some embodiments, R³ is L-rhamnitol. In some embodiments, R³ is D-fucitol.

In specific embodiments, R³ is L- or D-mannitol, L- or D-glycerol, or L- or D-arabitol. In specific embodiments, R³ is L- or D-mannitol. In some embodiments, R³ is mannitol.

In some embodiments, R³ is H, such as when the one or more lipids do not comprise a carbohydrate/sugar headgroup.

In some embodiments, R⁴ is C₅-C₁₂ alkyl. In some embodiments, R⁴ is C₅-C₁₀ alkyl. In some embodiments, R⁴ is C₅-C₇ alkyl. In some embodiments, R⁴ is C₅ or C₇ alkyl. In some embodiments, R⁴ is C₆ alkyl. In some embodiments, R⁴ is C₅ alkyl and the one or more lipids represented by a structure of Formula (I) are represented by a structure of Formula (I-A). In some embodiments, R⁴ is C₇ alkyl and the one or more lipids represented by a structure of Formula (I) are represented by a structure of Formula (I-B).

In some embodiments, the one or more lipids comprise a combination (e.g, mixture) of lipids. The one or more lipids may comprise one or more lipids described in Table 1.

TABLE 1
Lipid		Chemical
No.	Structure	Formula
1		C26H50O12
2		C36H68O15
3		C38H70O16
4		C40H74O16
5		C46H86O18

In some embodiments, the one or more lipids comprise lipid 1 (as described in Table 1) in an amount of at least 5 wt % (e.g., relative to the total amount of the one more lipids). In some embodiments, the one or more lipids comprise lipid 1 (as described in Table 1) in an amount of at least about 2 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, about 10 wt %, about 12 wt %, or about 14 wt %. In some embodiments, the one or more lipids comprise lipid 1 (as described in Table 1) in an amount of at most about 14 wt %, about 12 wt %, about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, or about 2 wt %. In some embodiments, the one or more lipids comprise lipid 1 (as described in Table 1) in an amount of about 2 wt % to about 14 wt %, about 4 wt % to about 12 wt %, about 7 wt % to about 12 wt %, about 8 wt % to about 10 wt %, about 5 wt % to about 9 wt %, or about 7 wt % to about 9 wt %. In some embodiments, the one or more lipids comprise lipid 1 (as described in Table 1) in an amount of about 2 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, about 10 wt %, about 12 wt %, or about 14 wt %. In some embodiments, the one or more lipids comprise lipid 1 (as described in Table 1) in an amount of about 9 wt %, such as described in FIG. 3.

In some embodiments, the one or more lipids comprise lipid 2 (as described in Table 1) in an amount of at least 20 wt % (e.g., relative to the total amount of the one or more lipids). In some embodiments, the one or more lipids comprise lipid 2 (as described in Table 1) in an amount of at least about 15 wt %, about 17 wt %, about 20 wt %, about 22 wt %, about 24 wt %, about 26 wt %, about 28 wt %, about 30 wt %, about 32 wt %, or about 34 wt %. In some embodiments, the one or more lipids comprise lipid 2 (as described in Table 1) in an amount of at most about 34 wt %, about 32 wt %, about 30 wt %, about 28 wt %, about 26 wt %, about 24 wt %, about 22 wt %, about 20 wt %, about 17 wt %, or about 15 wt %. In some embodiments, the one or more lipids comprise lipid 2 (as described in Table 1) in an amount of about 15 wt % to about 34 wt %, about 17 wt % to about 32 wt %, about 22 wt % to about 30 wt %, about 24 wt % to about 28 wt %, about 17 wt % to about 26 wt %, or about 22 wt % to about 26 wt %. In some embodiments, the one or more lipids comprise lipid 2 (as described in Table 1) in an amount of about 15 wt %, about 17 wt %, about 20 wt %, about 22 wt %, about 24 wt %, about 26 wt %, about 28 wt %, about 30 wt %, about 32 wt %, or about 34 wt %. In some embodiments, the one or more lipids comprise lipid 2 (as described in Table 1) in an amount of about 27 wt %, such as described in FIG. 3.

In some embodiments, the one or more lipids comprise lipid 3 (as described in Table 1) in an amount of at least 30 wt % (e.g., relative to the total amount of the one or more lipids). In some embodiments, the one or more lipids comprise lipid 3 (as described in Table 1) in an amount of at least about 25 wt %, about 27 wt %, about 30 wt %, about 32 wt %, about 34 wt %, about 36 wt %, about 38 wt %, about 40 wt %, about 42 wt %, or about 44 wt %. In some embodiments, the one or more lipids comprise lipid 3 (as described in Table 1) in an amount of at most about 44 wt %, about 42 wt %, about 40 wt %, about 38 wt %, about 36 wt %, about 34 wt %, about 32 wt %, about 30 wt %, about 27 wt %, or about 25 wt %. In some embodiments, the one or more lipids comprise lipid 3 (as described in Table 1) in an amount of about 25 wt % to about 44 wt %, about 27 wt % to about 42 wt %, about 32 wt % to about 40 wt %, about 34 wt % to about 38 wt %, about 27 wt % to about 36 wt %, or about 32 wt % to about 36 wt %. In some embodiments, the one or more lipids comprise lipid 3 (as described in Table 1) in an amount of about 25 wt %, about 27 wt %, about 30 wt %, about 32 wt %, about 34 wt %, about 36 wt %, about 38 wt %, about 40 wt %, about 42 wt %, or about 44 wt %. In some embodiments, the one or more lipids comprise lipid 3 (as described in Table 1) in an amount of about 37 wt %, such as described in FIG. 3.

In some embodiments, the one or more lipids comprise lipid 4 (as described in Table 1) in an amount of at least 15 wt % (e.g., relative to the total amount of the one or more lipids). In some embodiments, the one or more lipids comprise lipid 4 (as described in Table 1) in an amount of at least about 10 wt %, about 12 wt %, about 14 wt %, about 16 wt %, about 18 wt %, about 20 wt %, about 22 wt %, about 24 wt %, about 26 wt %, or about 28 wt %. In some embodiments, the one or more lipids comprise lipid 4 (as described in Table 1) in an amount of at most about 28 wt %, about 26 wt %, about 24 wt %, about 22 wt %, about 20 wt %, about 18 wt %, about 16 wt %, about 14 wt %, about 12 wt %, or about 10 wt %. In some embodiments, the one or more lipids comprise lipid 4 (as described in Table 1) in an amount of about 10 wt % to about 28 wt %, about 12 wt % to about 26 wt %, about 16 wt % to about 24 wt %, about 18 wt % to about 22 wt %, about 12 wt % to about 20 wt %, or about 16 wt % to about 20 wt %. In some embodiments, the one or more lipids comprise lipid 4 (as described in Table 1) in an amount of about 10 wt %, about 12 wt %, about 14 wt %, about 16 wt %, about 18 wt %, about 20 wt %, about 22 wt %, about 24 wt %, about 26 wt %, or about 28 wt %. In some embodiments, the one or more lipids comprise lipid 4 (as described in Table 1) in an amount of about 21 wt %, such as shown in FIG. 3.

In some embodiments, the one or more lipids comprise lipid 5 (as described in Table 1) in an amount of at least 3 wt % (e.g., relative to the total amount of the one or more lipids). In some embodiments, the one or more lipids comprise lipid 5 (as described in Table 1) in an amount of at least about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt %. In some embodiments, the one or more lipids comprise lipid 5 (as described in Table 1) in an amount of at most about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, about 3 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the one or more lipids comprise lipid 5 (as described in Table 1) in an amount of about 1 wt % to about 10 wt %, about 2 wt % to about 9 wt %, about 4 wt % to about 8 wt %, about 5 wt % to about 7 wt %, about 2 wt % to about 6 wt %, or about 4 wt % to about 6 wt %. In some embodiments, the one or more lipids comprise lipid 5 (as described in Table 1) in an amount of about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt %. In some embodiments, the one or more lipids comprise lipid 5 (as described in Table 1) in an amount of about 6 wt %, such as shown in FIG. 3.

In some embodiments, the ratio of C₁₂:C₁₀ alkyl chains in the lipid compositions may be from about 1:8 to about 1:15. In some embodiments, the ratio of C₁₂:C₁₀ alkyl chains may be about 1:8, 1:9, 1:10, 1:11, 1:12, or 1:13. In some embodiments, the ratio of C₁₂:C₁₀ alkyl chains may be about 1:13, such as described in FIG. 4.

In some embodiments, the relative amounts of lipids described in Table 1 may be determined by mass spectrometry, such as TOF-MS.

The presence of lipids (e.g., lipid 4) containing 12-carbon groups may be beneficial to SAF-production, as the average carbon chain length in aviation fuel is about 11.4 carbons. Additionally, having a mixture of different-length hydrocarbons may improve oil properties such as freeze point and viscosity.

In some embodiments, the one or more lipids as described herein is prepared by an organism. In some embodiments, the organism is a microorganism.

In some embodiments, the one or more lipids as described herein is bio-derived. In some embodiments, the one or more lipids is produced by an organism.

In some embodiments, the organism is within the family Dothioraceae. In some embodiments, the organism is within the genus Aureobasidium. In some embodiments, the organism is from the species aleuritis, apocryptum, dalgeri, harposporum, indicum, iranianum, khasianum, leucospermi, lilii, mangrovei, melanogenum, microstictum, namibiae, nigrum, pini, proteae, prunicola, pullulans, ribis, sanguinariae, subglaciale, thailandense, thujae-plicatae, tremulum, umbellulariae, or vaccinii. In some embodiments, the organism is from the species pullulans, melanogenum, or thailandense. In some embodiments, the organism is Aureobasidium pullulans. In some embodiments the organism is genetically modified. In some embodiments, the organism is Aureobasidium pullulans or a genetically modified version thereof. In some embodiments, a genetically modified version of the organism comprises a modification to a gene related to polymalic acid (e.g., PMA synthase), pullulan production (e.g., UDPG-pyrophosphorylase), oxygen binding hemoglobin (e.g., Vhb), a pathway activator gene (e.g., pacC), or a combination thereof. In some embodiments, a genetically modified version of the organism comprises knockout of polymalic acid (e.g., PMA synthase), knockout of pullulan production (e.g., UDPG-pyrophosphorylase), expression of oxygen binding hemoglobin (e.g., Vhb), overexpression of pathway activator gene (e.g., pacC), or a combination thereof.

In some embodiments, the organism is within the family Dothioraceae. In some embodiments, the organism is within the genus Aureobasidium. In some embodiments, the organism is from the species aleuritis, apocryptum, dalgeri, harposporum, indicum, iranianum, khasianum, leucospermi, lilii, mangrovei, melanogenum, microstictum, namibiae, nigrum, pini, proteae, prunicola, pullulans, ribis, sanguinariae, subglaciale, thailandense, thujae-plicatae, tremulum, umbellulariae, or vaccinii. In some embodiments, the organism is from the species pullulans, melanogenum, or thailandense. In some embodiments, the organism is Aureobasidium pullulans. In some embodiments the organism is genetically modified. In some embodiments, the organism is Aureobasidium pullulans or a genetically modified version thereof. In some embodiments, a genetically modified version of the organism comprises a modification to a gene related to polymalic acid (e.g., PMA synthase), pullulan production (e.g., UDPG-pyrophosphorylase), oxygen binding hemoglobin (e.g., Vhb), a pathway activator gene (e.g., pacC), or a combination thereof. In some embodiments, a genetically modified version of the organism comprises knockout of polymalic acid (e.g., PMA synthase), knockout of pullulan production (e.g., UDPG-pyrophosphorylase), expression of oxygen binding hemoglobin (e.g., Vhb), overexpression of pathway activator gene (e.g., pacC), or a combination thereof. In some embodiments, the organism produces at least 50 g/L titer of the one or more lipids.

In some embodiments, the methods comprise collecting the one or more lipids, such as the one or more lipids described elsewhere herein. In some embodiments, the collecting comprises liquid-liquid extraction, distillation, physical separation, mechanical cell disruption, supercritical fluid extraction, gravimetric separation, flash evaporation, or a combination thereof. In some embodiments, the collecting comprises liquid-liquid extraction. In some embodiments, the collecting comprises distillation. In some embodiments, the collecting comprises physical separation. In some embodiments, the collecting comprises mechanical cell disruption. In some embodiments, the collecting comprises supercritical fluid extraction. In some embodiments, the collecting comprises gravimetric separation. In some embodiments, the collecting comprises flash evaporation. In some embodiments, the collecting comprises liquid-liquid extraction, distillation, physical separation, and flash evaporation.

In some embodiments, the liquid-liquid extraction comprises use of a solvent. The solvent may be an organic solvent. The solvent may be a mixture of organic solvents. In some embodiments, the solvent is chloroform, methanol, butanol, isopropanol, hexane, toluene, petroleum ether, methyl ethyl ketone (MEK), acetonitrile, ethyl acetate, or a combination thereof. In some embodiments, the solvent is chloroform. In some embodiments, the solvent is methanol. In some embodiments, the solvent is butanol. In some embodiments, the solvent is isopropanol. In some embodiments, the solvent is hexane. In some embodiments, the solvent is toluene. In some embodiments, the solvent is petroleum ether. In some embodiments, the solvent is MEK. In some embodiments, the solvent is acetonitrile. In some embodiments, the solvent is ethyl acetate.

In some embodiments, waste streams produced from the extraction include solvent (e.g., organic solvent), organic/cellular residue, or a combination thereof.

In some embodiments, the liquid-liquid extraction comprises countercurrent liquid extraction, batch-wise (e.g., single stage) extraction, ultrasound-assisted extraction, or multistage countercurrent continuous extraction. In some embodiments, the liquid-liquid extraction comprises countercurrent liquid extraction.

In some embodiments, the liquid-liquid extraction is completed at any suitable temperature. In some embodiments, the liquid-liquid extraction is completed at a temperature of from about 25° C. to about 60° C. In some embodiments, the liquid-liquid extraction is completed at a temperature of from about 35° C. to about 50° C. In some embodiments, the liquid-liquid extraction is completed at a temperature of at least about 20° C., about 25° C., about 30° C., about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., or about 65° C. In some embodiments, the liquid-liquid extraction is completed at a temperature of at most about 65° C., about 60° C., about 55° C., about 50° C., about 45° C., about 40° C., about 35° C., about 30° C., about 25° C., or about 20° C. In some embodiments, the liquid-liquid extraction is completed at a temperature of from about 20° C. to about 65° C., about 25° C. to about 65° C., about 25° C. to about 60° C., about 30° C. to about 60° C., about 20° C. to about 50° C., about 30° C. to about 50° C., or about 35° C. to about 55° C. In some embodiments, the liquid-liquid extraction is completed at a temperature of about 20° C., about 25° C., about 30° C., about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., or about 65° C.

In some embodiments, the countercurrent liquid extraction comprises countercurrent liquid-liquid extraction. In some embodiments, the countercurrent liquid-liquid extraction is continuous countercurrent liquid-liquid extraction. In some embodiments, the liquid-liquid extraction is completed with a dynamic flow reactor.

In some embodiments, the distillation is water stripping distillation, steam distillation, vacuum distillation, azeotropic distillation, fractional distillation, or simple distillation. In some embodiments, the distillation is water stripping distillation. In some embodiments, the distillation is steam distillation. In some embodiments, the distillation is vacuum distillation. In some embodiments, the vacuum distillation is wiped-film distillation. In some embodiments, the distillation is azeotropic distillation. In some embodiments, the distillation is fractional distillation. In some embodiments, the distillation is simple distillation.

In some embodiments, the distillation comprises use of a reboiler and a condenser.

In some embodiments, the reboiler comprises a temperature of from about 80° C. to about 120° C. In some embodiments, the reboiler comprises a temperature of from about 90° C. to about 110° C. In some embodiments, the reboiler comprises a temperature of at least about 75° C., about 80° C., about 85° C., about 90° C., about 95° C., about 100° C., about 105° C., about 110° C., about 115° C., or about 120° C. In some embodiments, the reboiler comprises a temperature of at most about 120° C., about 115° C., about 110° C., about 105° C., about 100° C., about 95° C., about 90° C., about 85° C., about 80° C., or about 75° C. In some embodiments, the reboiler comprises a temperature of from about 75° C. to about 120° C., about 80° C. to about 120° C., about 80° C. to about 115° C., about 85° C. to about 115° C., about 75° C. to about 105° C., about 85° C. to about 105° C., or about 90° C. to about 110° C. In some embodiments, the reboiler comprises a temperature of about 75° C., about 80° C., about 85° C., about 90° C., about 95° C., about 100° C., about 105° C., about 110° C., about 115° C., or about 120° C.

In some embodiments, the condenser comprises a temperature of from about 50° C. to about 90° C. In some embodiments, the condenser comprises a temperature of from about 60° C. to about 80° C. In some embodiments, the condenser comprises a temperature of at least about 50° C., about 55° C., about 60° C., about 65° C., about 70° C., about 75° C., about 80° C., about 85° C., about 90° C., or about 95° C. In some embodiments, the condenser comprises a temperature of at most about 95° C., about 90° C., about 85° C., about 80° C., about 75° C., about 70° C., about 65° C., about 60° C., about 55° C., or about 50° C. In some embodiments, the condenser comprises a temperature of from about 50° C. to about 95° C., about 55° C. to about 95° C., about 55° C. to about 90° C., about 60° C. to about 90° C., about 50° C. to about 80° C., about 60° C. to about 80° C., or about 65° C. to about 85° C. In some embodiments, the condenser comprises a temperature of about 50° C., about 55° C., about 60° C., about 65° C., about 70° C., about 75° C., about 80° C., about 85° C., about 90° C., or about 95° C.

In some embodiments, the physical separation comprises centrifugation, decantation, or a combination thereof. In some embodiments, the physical separation comprises centrifugation. In some embodiments, the physical separation comprises decantation.

In some embodiments, the physical separation is completed in ambient conditions. In some embodiments, the physical separation is completed at a temperature of from about 25° C. to about 60° C. In some embodiments, the physical separation is completed at a temperature of from about 35° C. to about 50° C. In some embodiments, the physical separation is completed at a temperature of at least about 25° C., about 30° C., about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., or about 70° C. In some embodiments, the physical separation is completed at a temperature of at most about 70° C., about 65° C., about 60° C., about 55° C., about 50° C., about 45° C., about 40° C., about 35° C., about 30° C., or about 25° C. In some embodiments, the physical separation is completed at a temperature of from about 25° C. to about 70° C., about 30° C. to about 70° C., about 30° C. to about 65° C., about 35° C. to about 65° C., about 25° C. to about 55° C., about 35° C. to about 55° C., or about 40° C. to about 60° C. In some embodiments, the physical separation is completed at a temperature of about 25° C., about 30° C., about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., or about 70° C.

In some embodiments, the centrifugation is completed in ambient conditions. In some embodiments, the centrifugation is completed at a temperature of from about 0° C. to about 60° C. In some embodiments, the centrifugation is completed at a temperature of from about 35° C. to about 50° C. In some embodiments, the centrifugation is completed at a temperature of at least about 0° C., 5° C., 10° C., 15° C., 20° C., 25° C., about 30° C., about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., or about 70° C. In some embodiments, the centrifugation is completed at a temperature of at most about 70° C., about 65° C., about 60° C., about 55° C., about 50° C., about 45° C., about 40° C., about 35° C., about 30° C., or about 25° C. In some embodiments, the centrifugation is completed at a temperature of from about 25° C. to about 70° C., about 30° C. to about 70° C., about 30° C. to about 65° C., about 35° C. to about 65° C., about 25° C. to about 55° C., about 35° C. to about 55° C., or about 40° C. to about 60° C. In some embodiments, the centrifugation is completed at a temperature of about 25° C., about 30° C., about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., or about 70° C.

In some embodiments, the centrifugation comprises disc stack centrifugation. In some embodiments, the centrifugation comprises use of a three phase decanter centrifuge.

In some embodiments, the collecting comprises flash evaporation. In some embodiments, the flash evaporation comprises use of a flash drum. In some embodiments, the flash evaporation is completed at any suitable temperature. In some embodiments, the flash evaporation is completed at a temperature of from about 35° C. to about 55° C. In some embodiments, the flash evaporation is completed at a temperature of at least about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., about 70° C., about 75° C., or about 80° C. In some embodiments, the flash evaporation is completed at a temperature of at most about 80° C., about 75° C., about 70° C., about 65° C., about 60° C., about 55° C., about 50° C., about 45° C., about 40° C., or about 35° C. In some embodiments, the flash evaporation is completed at a temperature of from about 35° C. to about 80° C., about 40° C. to about 80° C., about 40° C. to about 75° C., about 45° C. to about 75° C., about 35° C. to about 65° C., about 45° C. to about 65° C., or about 50° C. to about 70° C. In some embodiments, the flash evaporation is completed at a temperature of about 35° C., about 40° C., about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., about 70° C., about 75° C., or about 80° C.

In some embodiments, before distillation, the method comprises solvent-extraction, such as to purify the one or more lipids provided herein. The solvent extraction may remove or reduce cellular debris, water, or other trace components. The solvent extraction may introduce organic solvent which may be removed and/or recovered during the subsequent distillation.

In some embodiments, the method comprises distillation. In some embodiments, the method comprises reacting the one or more lipids and distilling. In some embodiments, the method comprises reacting and distilling after the collecting of the one or more lipids (e.g., after preparation by the organism). In some embodiments, the reacting the one or more lipids and distilling produces one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones. In some embodiments, the method comprises reacting the lipids produced by the organism described elsewhere herein. In some embodiments, the distilling provides one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones. In some embodiments, the method comprises reacting at least a portion of the lipids to provide one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones. In some embodiments, the method comprises reacting at least a portion of the lipids and distilling to provide the 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone.

In some embodiments, the method comprises saponification. In some embodiments, the saponification comprises contacting at least a portion of the lipids with a base, such as potassium hydroxide, sodium hydroxide, lithium hydroxide, magnesium hydroxide, barium hydroxide, calcium hydroxide, potassium oxide, sodium oxide, lithium oxide, magnesium oxide, barium oxide, calcium oxide, a basic clay mineral (e.g., hydrotalcite), or a combination thereof. In some embodiments, the base is potassium hydroxide. In some embodiments, the base is sodium hydroxide. In some embodiments, the base is calcium hydroxide.

In some embodiments, the method comprises contacting the at least a portion of the lipids with a catalyst. In some embodiments, the method comprises contacting the at least portion of the lipids with an acid catalyst. In some embodiments, the contacting with a catalyst results in lactone formation.

In some embodiments, the acid catalyst is a weak acid (e.g., with a pK_a of between about 4 and about 7). In some embodiments, the acid catalyst is a strong acid (e.g., with a pK_a of less than about 4). In some embodiments, the acid catalyst is a mineral acid. In some embodiments, the acid catalyst is an organic acid. In some embodiments, the acid catalyst has a pK_a of less than about 5. In some embodiments, the acid catalyst is hydrochloric acid, sulfuric acid, hydrobromic acid, phosphoric acid, iodic acid, nitric acid, perchloric acid, or a combination thereof. In some embodiments, the acid catalyst is hydrochloric acid. In some embodiments, the acid catalyst is sulfuric acid. In some embodiments, the acid catalyst is hydrobromic acid. In some embodiments, the acid catalyst is phosphoric acid. In some embodiments, the acid catalyst is iodic acid. In some embodiments, waste streams produced from the reacting and/or distilling include salts resulting from the acid/base reactions as described herein (e.g., from the saponification or lactonization).

In some embodiments, the method does not comprise contacting the at least portion of the lipids with a catalyst (e.g., an acid catalyst, such as sulfuric acid). In some embodiments, the method comprises saponification (e.g., with a base) but does not comprise acidification. In some embodiments, the method comprises saponification (e.g., with a base) and thermally forming the resulting lactones.

In some embodiments, the contacting with the acid catalyst is before the distillation. In some embodiments, the contacting with the acid catalyst occurs concurrently with the distillation. In some embodiments, the acid catalyst is removed from the resulting composition before distillation. In some embodiments, the acid catalyst is not removed from the resulting composition before distillation.

In some embodiments, the distillation comprises simple distillation, fractional distillation, vacuum distillation, azeotropic distillation, spinning band distillation, wiped film distillation, or a combination thereof. In some embodiments, the distillation comprises simple distillation. In some embodiments, the distillation comprises fractional distillation. In some embodiments, the distillation comprises vacuum distillation. In some embodiments, the distillation comprises spinning band distillation. In some embodiments, the distillation comprises azeotropic distillation. In some embodiments, the distillation comprises wiped film distillation.

In some embodiments, the methods provided herein comprise wiped film distillation of at least a portion of the lipids to provide one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones. In some embodiments, the methods provided herein comprise simple distillation of at least a portion of the lipids to provide one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones. In some embodiments, the methods provided herein comprise fractional distillation of at least a portion of the lipids to provide one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones.

In some embodiments, the distillation is completed at a temperature of at least 200° C. In some embodiments, the distillation is completed at a temperature of about 180° C. to about 290° C. In some embodiments, the distillation is completed at a temperature of about 180° C. to about 230° C., about 180° C. to about 290° C., about 190° C. to about 230° C., about 190° C. to about 240° C., about 200° C. to about 230° C., about 200° C. to about 240° C., about 200° C. to about 250° C., about 200° C. to about 270° C., about 200° C. to about 290° C., about 210° C. to about 230° C., about 210° C. to about 240° C., about 210° C. to about 250° C., about 210° C. to about 270° C., about 210° C. to about 290° C., about 215° C. to about 230° C., about 215° C. to about 240° C., about 215° C. to about 250° C., about 215° C. to about 270° C., about 215° C. to about 290° C., about 220° C. to about 230° C., about 220° C. to about 240° C., about 220° C. to about 250° C., about 225° C. to about 230° C., about 225° C. to about 240° C., about 225° C. to about 250° C., about 230° C. to about 240° C., or about 230° C. to about 250° C. In some embodiments, the distillation is completed at a temperature of about 180° C., about 190° C., about 200° C., about 210° C., about 215° C., about 220° C., about 225° C., about 230° C., about 240° C., about 250° C., about 270° C., or about 290° C. In some embodiments, the distillation is completed at a temperature of from about 200° C. to about 250° C. In some embodiments, the distillation is completed at a temperature of from about 215° C. to about 235° C. In some embodiments, the distillation is completed at a temperature of at least about 180° C., about 190° C., about 200° C., about 210° C., about 215° C., about 220° C., about 225° C., about 230° C., about 240° C., about 250° C., or about 270° C. In some embodiments, the distillation is completed at a temperature of at least 200° C. In some embodiments, the distillation is completed at a temperature of at most about 225° C., about 230° C., about 240° C., about 250° C., about 270° C., or about 290° C. In some embodiments, the distillation is completed at a temperature of at least 250° C. (e.g., to thermally form the lactones). In some embodiments, the distillation is completed at a temperature of less than 200° C.

In some embodiments, the wiped film distillation is completed at a temperature of at least 200° C. In some embodiments, the wiped film distillation is completed at a temperature of about 180° C. to about 290° C. In some embodiments, the wiped film distillation is completed at a temperature of about 180° C. to about 230° C., about 180° C. to about 290° C., about 190° C. to about 230° C., about 190° C. to about 240° C., about 200° C. to about 230° C., about 200° C. to about 240° C., about 200° C. to about 250° C., about 200° C. to about 270° C., about 200° C. to about 290° C., about 210° C. to about 230° C., about 210° C. to about 240° C., about 210° C. to about 250° C., about 210° C. to about 270° C., about 210° C. to about 290° C., about 215° C. to about 230° C., about 215° C. to about 240° C., about 215° C. to about 250° C., about 215° C. to about 270° C., about 215° C. to about 290° C., about 220° C. to about 230° C., about 220° C. to about 240° C., about 220° C. to about 250° C., about 225° C. to about 230° C., about 225° C. to about 240° C., about 225° C. to about 250° C., about 230° C. to about 240° C., or about 230° C. to about 250° C. In some embodiments, the wiped film distillation is completed at a temperature of about 180° C., about 190° C., about 200° C., about 210° C., about 215° C., about 220° C., about 225° C., about 230° C., about 240° C., about 250° C., about 270° C., or about 290° C. In some embodiments, the wiped film distillation is completed at a temperature of from about 200° C. to about 250° C. In some embodiments, the wiped film distillation is completed at a temperature of from about 215° C. to about 235° C. In some embodiments, the wiped film distillation is completed at a temperature of at least about 180° C., about 190° C., about 200° C., about 210° C., about 215° C., about 220° C., about 225° C., about 230° C., about 240° C., about 250° C., or about 270° C. In some embodiments, the wiped film distillation is completed at a temperature of at least 200° C. In some embodiments, the wiped film distillation is completed at a temperature of at most about 225° C., about 230° C., about 240° C., about 250° C., about 270° C., or about 290° C. In some embodiments, the wiped film distillation is completed at a temperature of about 225° C.

In some embodiments, the distillation is completed at a temperature of less than about 200° C. In some embodiments, the distillation is completed at a temperature of at least about 100° C., about 110° C., about 120° C., about 130° C., about 140° C., about 150° C., about 160° C., about 180° C., about 190° C., or about 200° C. In some embodiments, the distillation is completed at a temperature of at most about 200° C., about 190° C., about 180° C., about 160° C., about 150° C., about 140° C., about 130° C., about 120° C., about 110° C., or about 100° C. In some embodiments, the distillation is completed at a temperature of from about 100° C. to about 200° C., about 110° C. to about 200° C., about 110° C. to about 190° C., about 120° C. to about 190° C., about 100° C. to about 160° C., about 120° C. to about 160° C., or about 130° C. to about 180° C. In some embodiments, the distillation is completed at a temperature of about 100° C., about 110° C., about 120° C., about 130° C., about 140° C., about 150° C., about 160° C., about 180° C., about 190° C., or about 200° C.

In some embodiments, the distillation is completed at reduced pressure. In some embodiments, the distillation is completed at a pressure of less than 1 atm. In some embodiments, the distillation is completed at a pressure of less than 0.5 atm. In some embodiments, the distillation is completed at a pressure of less than 0.1 atm. In some embodiments, the distillation is completed in a vacuum. In some embodiments, the distillation is completed at about 1 atm.

In some embodiments, the distillation is completed as a continuous process. “Continuous production process” or “continuous process” refer to processes which are designed to manufacture products constantly without interruption. In some embodiments, the distillation is completed as a batch process.

In some embodiments, the reacting and/or distillation provides a yield of the one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones of at least 30 wt %. In some embodiments, the reacting and/or distillation provides a yield of the one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones of at least 50 wt %. In some embodiments, the reacting and/or distillation provides a yield of the one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones of at least 70 wt %. In some embodiments, the reacting and/or distillation provides a yield of the one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones of about 30 wt %, 35 wt %, 40 wt %, 45 wt %, 50 wt %, 55 wt %, 60 wt %, 65 wt %, 70 wt %, 75 wt %, 80 wt %, 85 wt % 90 wt %, or 95 wt %.

In some embodiments, the reacting and/or distillation step provides mannitol (e.g., carbohydrate), a derivative of mannitol (e.g. C_5-6 molecules formed from the reaction of the carbohydrate with base or acid catalysts mentioned herein), the one or more lactones, or a combination thereof.

In some embodiments, waste streams produced from the reacting and/or distilling include water vapor.

The one or more lactones (e.g., 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone) produced by the methods herein may have a CI of less than 1 kg CO₂e/kg of lactone. The one or more lactones (e.g., 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone) produced by the methods herein may have a CI of less than 0.9 kg CO₂e/kg of lactone, 0.8 kg CO₂e/kg of lactone, 0.7 kg CO₂e/kg of lactone, 0.6 kg CO₂e/kg of lactone, 0.5 kg CO₂e/kg of lactone, 0.4 kg CO₂e/kg of lactone, 0.3 kg CO₂e/kg of lactone, or 0.2 kg CO₂e/kg of lactone. The one or more lactones (e.g., 5-hydroxy-2-decenoic acid-8-lactone and 3,5-dihydroxydecanoic acid-8-lactone) produced by the methods herein may have a CI of less than 0.1 kg CO₂e/kg of lactone. In some instances, the CI scores provided herein are calculated in accordance with EPA requirements for renewable identification number (RIN) credits. In some instances, the CI scores provided herein are calculated using the following boundaries: (a) >30% reduction from fossil Jet A for D6 RIN credits; (b) >50% reduction for D3 or D4 RIN credit compliance. In some instances, the CI scores provided herein are assessed cradle-to-gate.

In some embodiments, the composition further comprises vegetable oil, waste oil, animal fat, or a combination thereof. In some embodiments, the composition comprises vegetable oil. In some embodiments, the composition comprises waste oil. In some embodiments, the composition comprises animal fat.

In some embodiments, the composition further comprises soybean oil, corn oil, rapeseed oil (e.g., canola oil), jatropha oil, sunflower oil, castor bean oil, palm oil, peanut oil, camelina oil, or a combination thereof. In some embodiments, the composition comprises soybean oil. In some embodiments, the composition comprises rapeseed oil. In some embodiments, the composition comprises peanut oil. In some embodiments, the composition comprises camelina oil. In some embodiments, the composition comprises corn oil. In some embodiments, the composition comprises distillers corn oil. In some embodiments, the composition comprises canola oil. In some embodiments, the composition comprises jatropha oil. In some embodiments, the composition comprises sunflower oil. In some embodiments, the composition comprises castor bean oil. In some embodiments, the composition comprises palm oil.

In some embodiments, the composition comprises waste oil, animal fats, or a combination thereof. In some embodiments, the waste oil or animal fat is cooking oil, yellow grease, brown grease, tall oil, tall oil fatty acids, algae oils, bacterial oils, yeast oils, tallow, lard, ghee, or a combination thereof.

In some embodiments, the composition further comprises hydrogen.

In some embodiments, the composition comprises the substituted or unsubstituted (e.g., saturated or unsaturated) lactone in an amount of at least 40 wt %. In some embodiments, the composition comprises the substituted or unsubstituted (e.g., saturated or unsaturated) lactone in an amount of at least 60 wt %. In some embodiments, the composition comprises the substituted or unsubstituted (e.g., saturated or unsaturated) lactone in an amount of at least about 20 wt %, about 30 wt %, about 40 wt %, about 50 wt %, about 60 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, or about 90 wt %. In some embodiments, the composition comprises the substituted or unsubstituted (e.g., saturated or unsaturated) lactone in an amount of at most about 90 wt %, about 85 wt %, about 80 wt %, about 75 wt %, about 70 wt %, about 60 wt %, about 50 wt %, about 40 wt %, about 30 wt %, or about 20 wt %. In some embodiments, the composition comprises the substituted or unsubstituted (e.g., saturated or unsaturated) lactone in an amount of from about 20 wt % to about 90 wt %, about 30 wt % to about 90 wt %, about 30 wt % to about 85 wt %, about 40 wt % to about 85 wt %, about 20 wt % to about 75 wt %, about 40 wt % to about 75 wt %, or about 50 wt % to about 80 wt %. In some embodiments, the composition comprises the substituted or unsubstituted (e.g., saturated or unsaturated) lactone in an amount of about 20 wt %, about 30 wt %, about 40 wt %, about 50 wt %, about 60 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, or about 90 wt %.

In some embodiments, the composition comprises the 5-hydroxy-2-decenoic acid-8-lactone and/or 3,5-hydroxydecanoic acid-8-lactone in an amount of at least 40 wt %. In some embodiments, the composition comprises the 5-hydroxy-2-decenoic acid-8-lactone and/or 3,5-hydroxydecanoic acid-δ-lactone in an amount of at least 60 wt %. In some embodiments, the composition comprises the 5-hydroxy-2-decenoic acid-δ-lactone and/or 3,5-hydroxydecanoic acid-δ-lactone in an amount of at least about 20 wt %, about 30 wt %, about 40 wt %, about 50 wt %, about 60 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, or about 90 wt %. In some embodiments, the composition comprises the 5-hydroxy-2-decenoic acid-δ-lactone and/or 3,5-hydroxydecanoic acid-δ-lactone in an amount of at most about 90 wt %, about 85 wt %, about 80 wt %, about 75 wt %, about 70 wt %, about 60 wt %, about 50 wt %, about 40 wt %, about 30 wt %, or about 20 wt %. In some embodiments, the composition comprises the 5-hydroxy-2-decenoic acid-δ-lactone and/or 3,5-hydroxydecanoic acid-δ-lactone in an amount of from about 20 wt % to about 90 wt %, about 30 wt % to about 90 wt %, about 30 wt % to about 85 wt %, about 40 wt % to about 85 wt %, about 20 wt % to about 75 wt %, about 40 wt % to about 75 wt %, or about 50 wt % to about 80 wt %. In some embodiments, the composition comprises the 5-hydroxy-2-decenoic acid-δ-lactone and/or 3,5-hydroxydecanoic acid-δ-lactone in an amount of about 20 wt %, about 30 wt %, about 40 wt %, about 50 wt %, about 60 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, or about 90 wt %.

In some embodiments, the methods provided herein comprise providing the composition comprising the one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones, the lipids (e.g., one or more lipids described elsewhere herein), or a combination thereof for processing to produce a crude fuel mixture.

In some embodiments, the method comprises providing a composition comprising the one or more substituted or unsubstituted (e.g., saturated or unsaturated) lactones, such as the one or more substituted or unsubstituted lactones described elsewhere herein. In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-hydroxydecanoic acid-δ-lactone.

In some embodiments, the method comprises providing a composition comprising the lipids (e.g., one or more lipids described elsewhere herein). In some embodiments, the method comprises providing a composition comprising the lipids (e.g., one or more lipids described elsewhere herein), 5-hydroxy-2-decenoic acid-δ-lactone, and 3,5-hydroxydecanoic acid-δ-lactone.

The method may comprise processing the composition (e.g., comprising the substituted or unsubstituted lactones, lipids, or combination thereof) to produce a crude fuel mixture.

In some embodiments, the processing comprises hydrotreatment, product separation, isomerization, oligomerization, hydrodeoxygenation, cracking, hydrocracking, or a combination thereof. In some embodiments, the processing comprises a series of steps comprising a combination of one or more of hydrotreatment, product separation, isomerization, and cracking. In some embodiments, the processing comprises product separation and recycling of light components back to processing. In some embodiments, the processing comprises isomerization. In some embodiments, the processing comprises cracking.

In some embodiments, the method comprises product separation. In some embodiments, the method comprises isomerization. In some embodiments, the method comprises cracking. In some embodiments, the method comprises recycling of light components back to processing.

In some embodiments, the method comprises hydrotreatment. In some embodiments, the hydrotreatment comprises use of a catalyst, catalyst support, or a combination thereof. In some embodiments, the hydrotreatment comprises use of a catalyst. In some embodiments, the hydrotreatment comprises use of a catalyst support.

In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises a sulfide, carbide, phosphide, or nanoparticle of Pd, Pt, Ni, Ru, Mo, Co, Ag, Cu, Sn, W, Rh, Au, Ir, Fe or a combination thereof. In some embodiments, the catalyst is Pd, Pt, or Ni. In some embodiments, the catalyst is Pd. In some embodiments, the catalyst is Pt. In some embodiments, the catalyst is Ni. In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises a sulfide of Pd, Pt, Ni, Ru, Mo, Co, Ag, Cu, Sn, W, Rh, Au, Ir, Fe or a combination thereof. In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises CoMoSx, NiMoSx, WS2, MoS2, or a combination thereof. In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises CoMoS. In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises NiMOS (NiMo sulfide). In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises WS2. In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises MoS2. In some embodiments, the catalyst is Pt. In some embodiments, the catalyst is Pd. In some embodiments, the catalyst is Ni.

In some embodiments, the catalyst support (e.g., used in the hydrotreatment) comprises carbon, a metal oxide, a zeolite, a zeotype, or a combination thereof. In some embodiments, the catalyst (e.g., used in the hydrotreatment) comprises MoC, Mo₂C (molybdenum carbide), or a combination thereof.

In some embodiments, the catalyst support (e.g., used in the hydrotreatment) comprises carbon.

In some embodiments, the catalyst support (e.g., used in the hydrotreatment) comprises a metal oxide. In some embodiments, the metal oxide is TiO2, Al2O3, SiO2, ZrO2, or CeO2. In some embodiments, the metal oxide is TiO2. In some embodiments, the metal oxide is Al2O3. In some embodiments, the metal oxide is SiO2. In some embodiments, the metal oxide is ZrO2. In some embodiments, the metal oxide is CeO2.

In some embodiments, the catalyst support (e.g., used in the hydrotreatment) comprises a zeolite. In some embodiments, the zeolite is beta zeolite, faujasite, mordenite, ZSM-5, ZSM-22, or ZSM-23. In some embodiments, the zeolite is beta zeolite. In some embodiments, the zeolite is fa jasite. In some embodiments, the zeolite is mordenite. In some embodiments, the zeolite is ZSM-5. In some embodiments, the zeolite is ZSM-22. In some embodiments, the zeolite is ZSM-23.

In some embodiments, the catalyst support (e.g., used in the hydrotreatment) comprises a zeotype. In some embodiments, the zeotype is SAPO-11, SAPO-5, or SAPO-34. In some embodiments, the zeotype is SAPO-11. In some embodiments, the zeotype is SAPO-5. In some embodiments, the zeotype is SAPO-34.

In some embodiments, the hydrotreatment comprises use of a catalyst/catalyst support combination. In some embodiments, the catalyst/catalyst support combination comprises a catalyst (as described elsewhere herein) and a metal oxide (as described elsewhere herein). In some embodiments, the catalyst/catalyst support combination comprises NiMOS (NiMo sulfide) and a metal oxide. In some embodiments, the catalyst/catalyst support combination comprises NiMOS and TiO2, Al2O3, SiO₂, ZrO2, or CeO2. In some embodiments, the catalyst/catalyst support combination comprises NiMOS and Al2O3. In some embodiments, the catalyst/catalyst support is NiMOS (NiMo sulfide)/Al₂O₃. In some embodiments, the catalyst/catalyst support is Ni/SAPO-11. In some embodiments, the catalyst/catalyst support is Pt/SAPO-11. In some embodiments, the catalyst/catalyst support is Pd/C. In some embodiments, the catalyst/catalyst support 5% Pd/C. In some embodiments, the catalyst/support combination comprises Mo₂C and a metal oxide.

The hydrotreatment described herein may comprise hydrogenation, hydrodeoxygenation, decarboxylation, oligomerization, and decarbonylation reactions, or any combination thereof. The hydrotreatment described herein may comprise hydrogenation, hydrodeoxygenation, decarboxylation, and decarbonylation reactions, or any combination thereof. In some embodiments, the hydrotreatment comprises hydrogenation. In some embodiments, the hydrotreatment comprises hydrodeoxygenation. In some embodiments, the hydrotreatment comprises decarboxylation. In some embodiments, the hydrotreatment comprises decarbonylation. In some embodiments, the hydrotreatment comprises oligomerization.

In some embodiments, the hydrotreatment is completed at any suitable temperature, such as to produce deoxygenated hydrocarbons, carbon dioxide, carbon monoxide, water, or any combination thereof. In some embodiments, the hydrotreatment is completed at any suitable temperature, such as to produce alkanes, carbon dioxide, carbon monoxide, water, or any combination thereof. In some embodiments, the hydrotreatment is completed at a temperature of about 250° C. to about 400° C. In some embodiments, the hydrotreatment is completed at a temperature of about 300° C. to about 400° C. In some embodiments, the hydrotreatment is completed at a temperature of about 320° C. to about 360° C. In some embodiments, the hydrotreatment is completed at a temperature of from about 280° C. to about 400° C., from about 290° C. to about 400° C., from about 310° C. to about 400° C., from about 320° C. to about 380° C., from about 320° C. to about 360° C., or from about 320° C. to about 350° C. In some embodiments, the hydrotreatment is completed at a temperature of about 250° C., about 260° C., about 280° C., about 300° C., about 310° C., about 320° C., about 330° C., about 340° C., about 350° C., about 370° C., about 390° C., or about 400° C. In some embodiments, the hydrotreatment is completed at a temperature of at least about 250° C., about 260° C., about 280° C., about 300° C., about 310° C., about 320° C., about 330° C., or about 340° C. In some embodiments, the hydrotreatment is completed at a temperature of at most about 340° C., about 350° C., about 370° C., about 390° C., or about 400° C. In some embodiments, the hydrotreatment is completed at a temperature of at least 250° C. In some embodiments, the hydrotreatment is completed at a temperature of at least 300° C. In some embodiments, the hydrotreatment is completed at a temperature of about 340° C.

In some embodiments, the hydrotreatment is completed at any suitable pressure. In some embodiments, the hydrotreatment is completed at a pressure of at least about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the hydrotreatment is completed at a pressure of at most about 45 atm, about 40 atm, about 35 atm, about 30 atm, about 25 atm, about 20 atm, about 15 atm, about 10 atm, about 5 atm, or about 1 atm. In some embodiments, the hydrotreatment is completed at a pressure of about 1 atm to about 300 atm, about 50 atm to about 250 atm, about 100 atm to about 200 atm, or about 150 atm. In some embodiments, the hydrotreatment is completed at a pressure of about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the hydrotreatment is completed at a pressure of at least 10 atm. In some embodiments, the hydrotreatment is completed at a pressure of at least 20 atm. In some embodiments, the hydrotreatment is completed at a pressure of about 10 atm to about 40 atm. In some embodiments, the hydrotreatment is completed at a pressure of about 20 atm to about 40 atm. In some embodiments, the hydrotreatment is completed at a pressure of about 30 atm.

In some embodiments, the hydrotreatment comprises any suitable weight hourly space velocity (WHSV). “Weight hourly space velocity” may refer to the ratio of weight of reactant entering the reactor per hour to weight of catalyst. In some embodiments, the hydrotreatment comprises a WHSV of at least about 0.2 hr⁻¹, about 0.5 hr⁻¹, about 0.8 hr⁻¹, about 1 hr⁻¹, about 1.5 hr⁻¹, about 2 hr⁻¹, about 3 hr⁻¹, about 4 hr⁻¹, about 6 hr⁻¹, or about 8 hr⁻¹. In some embodiments, the hydrotreatment comprises a WHSV of at most about 8 hr⁻¹, about 6 hr⁻¹, about 4 hr⁻¹, about 3 hr⁻¹, about 2 hr⁻¹, about 1.5 hr⁻¹, about 1 hr⁻¹, about 0.8 hr⁻¹, about 0.5 hr⁻¹, or about 0.2 hr⁻¹. In some embodiments, the hydrotreatment comprises a WHSV of about 0.2 hr⁻¹ to about 8 hr⁻¹, about 0.5 hr⁻¹ to about 6 hr⁻¹, about 0.5 hr⁻¹ to about 2 hr⁻¹, about 0.8 hr⁻¹ to about 1.5 hr⁻¹, about 1 hr⁻¹ to about 4 hr⁻¹, or about 1 hr⁻¹ to about 2 hr⁻¹. In some embodiments, the hydrotreatment comprises a WHSV of about 0.2 hr⁻¹, about 0.5 hr⁻¹, about 0.8 hr⁻¹, about 1 hr⁻¹, about 1.5 hr⁻¹, about 2 hr⁻¹, about 3 hr⁻¹, about 4 hr⁻¹, about 6 hr⁻¹, or about 8 hr⁻¹. In some embodiments, the hydrotreatment comprises a WHSV of about 1 hr⁻¹.

In some embodiments, the processing comprises product separation. In some embodiments, the method comprises product separation. In some embodiments, the product separation comprises flash evaporation. In some embodiments, the method comprises flash evaporation. In some embodiments, the flash evaporation comprises use of a flash drum. In some embodiments, the flash evaporation results in the purification of hydrocarbons from the hydrotreatment.

In some embodiments, the flash evaporation is completed at any suitable temperature. In some embodiments, the flash evaporation is completed at a temperature of at least about 120° C., about 130° C., about 140° C., about 150° C., about 160° C., about 165° C., about 170° C., about 180° C., about 190° C., or about 200° C. In some embodiments, the flash evaporation is completed at a temperature of at most about 230° C., about 220° C., about 200° C., about 190° C., about 180° C., about 170° C., about 165° C., about 160° C., about 150° C., about 140° C., about 130° C., or about 120° C. In some embodiments, the flash evaporation is completed at a temperature of about 120° C. to about 230° C., about 120° C. to about 200° C., about 130° C. to about 190° C., about 150° C. to about 180° C., about 160° C. to about 170° C., about 130° C. to about 165° C., or about 150° C. to about 165° C. In some embodiments, the flash evaporation is completed at a temperature of about 120° C., about 130° C., about 140° C., about 150° C., about 160° C., about 165° C., about 170° C., about 180° C., about 190° C., about 200° C., about 210° C., about 220° C., or about 230° C. In some embodiments, the flash evaporation is completed at a temperature of at least about 150° C. In some embodiments, the flash evaporation is completed at a temperature of from about 150° C. to about 180° C. In some embodiments, the flash evaporation is completed at a temperature of about 160° C. In some embodiments, the flash evaporation is completed at a temperature of about 165° C. In some embodiments, the flash evaporation is completed at a temperature of about 170° C.

In some embodiments, the product separation is completed at any suitable temperature. In some embodiments, the product separation is completed at a temperature of at least about 120° C., about 130° C., about 140° C., about 150° C., about 160° C., about 165° C., about 170° C., about 180° C., about 190° C., about 200° C., about 210° C., about 220° C., or about 230° C. In some embodiments, the product separation is completed at a temperature of at most about 230° C., about 220° C., about 200° C., about 190° C., about 180° C., about 170° C., about 165° C., about 160° C., about 150° C., about 140° C., about 130° C., or about 120° C. In some embodiments, the product separation is completed at a temperature of about 120° C. to about 230° C., about 120° C. to about 200° C., about 130° C. to about 190° C., about 150° C. to about 180° C., about 160° C. to about 170° C., about 130° C. to about 165° C., or about 150° C. to about 165° C. In some embodiments, the product separation is completed at a temperature of about 120° C., about 130° C., about 140° C., about 150° C., about 160° C., about 165° C., about 170° C., about 180° C., about 190° C., or about 200° C. In some embodiments, the product separation is completed at a temperature of at least about 150° C. In some embodiments, the product separation is completed at a temperature of from about 150° C. to about 180° C. In some embodiments, the product separation is completed at a temperature of about 160° C. In some embodiments, the product separation is completed at a temperature of about 165° C. In some embodiments, the product separation is completed at a temperature of about 170° C.

In some embodiments, the flash evaporation is completed at any suitable pressure. In some embodiments, the flash evaporation is completed in a vacuum. In some embodiments, the flash evaporation is completed at a pressure of less than about 0.5 atm, 0.4 atm, 0.3 atm, 0.2 atm, or 0.1 atm. In some embodiments, evaporation is completed at a pressure of less than 0.1 atm. In some embodiments, the flash evaporation is completed at a pressure of at least about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the flash evaporation is completed at a pressure of at most about 45 atm, about 40 atm, about 35 atm, about 30 atm, about 25 atm, about 20 atm, about 15 atm, about 10 atm, about 5 atm, or about 1 atm. In some embodiments, the flash evaporation is completed at a pressure of about 1 atm to about 45 atm, about 5 atm to about 40 atm, about 10 atm to about 30 atm, about 15 atm to about 25 atm, about 20 atm to about 40 atm, or about 20 atm to about 30 atm. In some embodiments, the flash evaporation is completed at a pressure of about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the flash evaporation is completed at a pressure of at least 10 atm. In some embodiments, the flash evaporation is completed at a pressure of at least 15 atm. In some embodiments, the flash evaporation is completed at a pressure of about 20 atm.

In some embodiments, the product separation is completed at any suitable pressure. In some embodiments, the product separation is completed at a pressure of at least about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the product separation is completed at a pressure of at most about 45 atm, about 40 atm, about 35 atm, about 30 atm, about 25 atm, about 20 atm, about 15 atm, about 10 atm, about 5 atm, or about 1 atm. In some embodiments, the product separation is completed at a pressure of about 1 atm to about 45 atm, about 5 atm to about 40 atm, about 10 atm to about 30 atm, about 15 atm to about 25 atm, about 20 atm to about 40 atm, or about 20 atm to about 30 atm. In some embodiments, the product separation is completed at a pressure of about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the product separation is completed at a pressure of at least 10 atm. In some embodiments, the product separation is completed at a pressure of at least 15 atm. In some embodiments, the product separation is completed at a pressure of about 20 atm.

In some embodiments, the resulting products from the product separation (e.g., flash evaporation distillate or bottoms) are used in the isomerization and/or cracking described herein.

In some embodiments, the processing comprises isomerization and/or cracking. In some embodiments, the method comprises isomerization and/or cracking. In some embodiments, the isomerization and/or cracking comprise use of a catalyst, a catalyst support, or a combination thereof. In some embodiments, the isomerization and/or cracking comprise use of a catalyst. In some embodiments, the isomerization and/or cracking comprise use of a catalyst support. In some embodiments, the isomerization and/or cracking comprise use of the same catalyst/catalyst support used for hydrotreating. In some embodiments, isomerization and/or cracking occur concurrently with hydrotreating.

In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises a sulfide, carbide, phosphide, nitride, or nanoparticle of Pd, Pt, Ni, Ru, Mo, Co, Ag, Cu, Sn, W, Rh, Au, Ir, Fe or a combination thereof. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises a sulfide of Pd, Pt, Ni, Ru, Mo, Co, Ag, Cu, Sn, W, Rh, Au, Ir, Fe or a combination thereof. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Pd, Pt, Ni, Ag, or W. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Pd. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Pt. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Ni. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Ag. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises W. In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Rh, In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Au, In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Ir, In some embodiments, the catalyst (e.g., used in the isomerization and/or cracking) comprises Fe.

In some embodiments, the catalyst support (e.g., used in the isomerization and/or cracking) comprises carbon, a metal oxide, a zeolite, a zeotype, or a combination thereof.

In some embodiments, the catalyst support (e.g., used in the isomerization and/or cracking) comprises carbon.

In some embodiments, the catalyst support (e.g., used in the isomerization and/or cracking) comprises a metal oxide. In some embodiments, the metal oxide is TiO2, Al₂O₃, SiO₂, ZrO2, or CeO2. In some embodiments, the metal oxide is TiO2. In some embodiments, the metal oxide is Al2O3. In some embodiments, the metal oxide is SiO2. In some embodiments, the metal oxide is ZrO2. In some embodiments, the metal oxide is CeO2.

In some embodiments, the catalyst support (e.g., used in the isomerization and/or cracking) comprises a zeolite. In some embodiments, the zeolite is beta zeolite, faujasite, mordenite, ZSM-5, ZSM-22, or ZSM-23. In some embodiments, the zeolite is beta zeolite. In some embodiments, the zeolite is faujasite. In some embodiments, the zeolite is mordenite. In some embodiments, the zeolite is ZSM-5. In some embodiments, the zeolite is ZSM-22. In some embodiments, the zeolite is ZSM-23.

In some embodiments, the catalyst support (e.g., used in the isomerization and/or cracking) comprises a zeotype. In some embodiments, the zeotype is SAPO-11, SAPO-5, or SAPO-34. In some embodiments, the zeotype is SAPO-11. In some embodiments, the zeotype is SAPO-5. In some embodiments, the zeotype is SAPO-34.

In some embodiments, the isomerization and/or cracking comprises use of a catalyst/catalyst support combination. In some embodiments, the catalyst/catalyst support combination comprises a catalyst (as described elsewhere herein) and a zeotype (as described elsewhere herein). In some embodiments, the catalyst/catalyst support combination comprises Pt and a zeotype. In some embodiments, the catalyst/catalyst support combination comprises Pt and SAPO-11, SAPO-5, or SAPO-34. In some embodiments, the catalyst/catalyst support combination comprises Pt and SAPO-11. In some embodiments, the catalyst/catalyst support combination comprises Pt and SAPO-5. In some embodiments, the catalyst/catalyst support combination comprises Pt and SAPO-34. In some embodiments, the catalyst/catalyst support combination comprises Pd and carbon (e.g., 5% Pd/C).

In some embodiments, the isomerization and/or cracking is completed at any suitable temperature. In some embodiments, the isomerization and/or cracking is completed at a temperature of about 250° C. to about 450° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of about 300° C. to about 450° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of about 320° C. to about 400° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of from about 280° C. to about 400° C., from about 290° C. to about 400° C., from about 310° C. to about 400° C., from about 320° C. to about 380° C., from about 320° C. to about 360° C., or from about 320° C. to about 350° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of about 250° C., about 260° C., about 280° C., about 300° C., about 310° C., about 320° C., about 330° C., about 340° C., about 350° C., about 370° C., about 390° C., or about 400° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of at least about 250° C., about 260° C., about 280° C., about 300° C., about 310° C., about 320° C., about 330° C., or about 340° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of at most about 350° C., about 370° C., about 390° C., or about 400° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of at least 250° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of at least 300° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of about 350° C. In some embodiments, the isomerization and/or cracking is completed at a temperature of about 375° C.

In some embodiments, the isomerization and/or cracking is completed at any suitable pressure. In some embodiments, the isomerization and/or cracking is completed at a pressure of at least about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of at most about 300 atm, about 250 atm, about 200 atm, about 150 atm, about 100 atm, about 50 atm, or about 1 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of about 1 atm to about 45 atm, about 5 atm to about 40 atm, about 10 atm to about 30 atm, about 15 atm to about 25 atm, about 20 atm to about 40 atm, or about 20 atm to about 30 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of about 1 atm, about 5 atm, about 10 atm, about 15 atm, about 20 atm, about 25 atm, about 30 atm, about 35 atm, about 40 atm, or about 45 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of from about 10 atm to about 30 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of at least 5 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of at least 10 atm. In some embodiments, the isomerization and/or cracking is completed at a pressure of about 20 atm.

In some embodiments, impurities, such as CO₂, waste water, or a combination thereof are removed from the isomerization and/or cracking. The impurities, such as CO₂, waste water, or a combination thereof may be recycled and reused in reaction steps described elsewhere herein (105, 210).

The methods provided herein (e.g., the processing herein) may not require deodorization, neutralization, degumming, bleaching, or any combination thereof, as a result of the use of e.g., 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone herein. The use of 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone as precursors to sustainable fuels may reduce or avoid the need for removal of impurities, particulates, odors, and the like by degumming, bleaching, and deodorization.

In some embodiments, the methods provided herein provide a crude fuel mixture, such as after isomerization and/or cracking. In some embodiments, the crude fuel mixture comprises one or more of C_>14 alkanes, C₉-C₁₄ alkanes, C_<9 alkanes, aromatic species, cyclic species, alkenes, and oxygenated species. In some embodiments, the crude fuel mixture comprises any of the species found in Tables 2A, 3A, 4A, 5A, 6A, 7A, or 8A.

In some embodiments, the crude fuel mixture comprises C_>14 alkanes. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of at least about 0.1 wt %, about 0.2 wt %, about 0.3 wt %, about 0.4 wt %, about 0.5 wt %, about 0.7 wt %, about 1 wt %, about 1.2 wt %, about 1.5 wt %, or about 2 wt %. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of at most about 2 wt %, about 1.5 wt %, about 1.2 wt %, about 1 wt %, about 0.7 wt %, about 0.5 wt %, about 0.4 wt %, about 0.3 wt %, about 0.2 wt %, or about 0.1 wt %. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of from about 0.1 wt % to about 2 wt %, about 0.2 wt % to about 2 wt %, about 0.2 wt % to about 1.5 wt %, about 0.3 wt % to about 1.5 wt %, about 0.1 wt % to about 1 wt %, about 0.3 wt % to about 1 wt %, or about 0.4 wt % to about 1.2 wt %. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of about 0.1 wt %, about 0.2 wt %, about 0.3 wt %, about 0.4 wt %, about 0.5 wt %, about 0.7 wt %, about 1 wt %, about 1.2 wt %, about 1.5 wt %, or about 2 wt %. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of at least about 0.2 wt %. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of from about 0.1 wt % to about 1.5 wt %. In some embodiments, the crude fuel mixture comprises the C_>14 alkanes in an amount of at most about 2 wt %.

In some embodiments, the crude fuel mixture comprises C₉-C₁₄ alkanes. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of at least about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, or about 85 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of at most about 85 wt %, about 80 wt %, about 75 wt %, about 70 wt %, about 65 wt %, about 60 wt %, about 55 wt %, about 50 wt %, about 45 wt %, or about 40 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of from about 40 wt % to about 85 wt %, about 45 wt % to about 85 wt %, about 45 wt % to about 80 wt %, about 50 wt % to about 80 wt %, about 40 wt % to about 70 wt %, about 50 wt % to about 70 wt %, or about 55 wt % to about 75 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, or about 85 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of at least about 40 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of at least about 80 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of at most about 90 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of from about 40 wt % to about 90 wt %. In some embodiments, the crude fuel mixture comprises the C₉-C₁₄ alkanes in an amount of from about 60 wt % to about 85 wt %. Non-limiting examples of C₉-C₁₄ alkanes include nonane, decane, 4-methyl octane, 3-methyl octane, and undecane.

In some embodiments, the crude fuel mixture comprises C_<9 alkanes. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of at least about 5 wt %, about 8 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 22 wt %, about 25 wt %, or about 28 wt %. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of at most about 28 wt %, about 25 wt %, about 22 wt %, about 20 wt %, about 18 wt %, about 15 wt %, about 12 wt %, about 10 wt %, about 8 wt %, or about 5 wt %. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of from about 5 wt % to about 28 wt %, about 8 wt % to about 28 wt %, about 8 wt % to about 25 wt %, about 10 wt % to about 25 wt %, about 5 wt % to about 20 wt %, about 10 wt % to about 20 wt %, or about 12 wt % to about 22 wt %. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of about 5 wt %, about 8 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 22 wt %, about 25 wt %, or about 28 wt %. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of from about 5 wt % to about 20 wt %. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of at least 7 wt %. In some embodiments, the crude fuel mixture comprises the C_<9 alkanes in an amount of at most 20 wt %. Non-limiting examples of C_<9 alkanes include heptane, pentane, hexane, octane, pentane, and butane.

In some embodiments, the crude fuel mixture comprises aromatic species. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of at least about 1 wt %, about 2 wt %, about 4 wt %, about 6 wt %, about 8 wt %, about 10 wt %, about 12 wt %, about 14 wt %, about 16 wt %, or about 18 wt %. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of at most about 18 wt %, about 16 wt %, about 14 wt %, about 12 wt %, about 10 wt %, about 8 wt %, about 6 wt %, about 4 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of from about 1 wt % to about 18 wt %, about 2 wt % to about 18 wt %, about 2 wt % to about 16 wt %, about 4 wt % to about 16 wt %, about 1 wt % to about 12 wt %, about 4 wt % to about 12 wt %, or about 6 wt % to about 14 wt %. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of about 1 wt %, about 2 wt %, about 4 wt %, about 6 wt %, about 8 wt %, about 10 wt %, about 12 wt %, about 14 wt %, about 16 wt %, or about 18 wt %. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of from about 12 wt % to about 10 wt %. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of at least 1 wt %. In some embodiments, the crude fuel mixture comprises the aromatic species in an amount of at most 10 wt %. Non-limiting examples of aromatic species include 1-ethyl-2-methyl benzene, ethyl benzene, butyl benzene, toluene, and propyl benzene.

In some embodiments, the crude fuel mixture comprises cyclic species. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of at least about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt %. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of at most about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, about 3 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of from about 1 wt % to about 10 wt %, about 2 wt % to about 10 wt %, about 2 wt % to about 9 wt %, about 3 wt % to about 9 wt %, about 1 wt % to about 7 wt %, about 3 wt % to about 7 wt %, or about 4 wt % to about 8 wt %. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt %. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of at least 2 wt %. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of at most 7 wt %. In some embodiments, the crude fuel mixture comprises the cyclic species in an amount of from about 2 wt % to about 8 wt %. Non-limiting examples of cyclic species include 1,5-diisopropyl-2,3-dimethyl-cyclohexane, decahydronaphthalene, 1,2,4,5-tetrahydronaphthalene, pentyl-cyclopentane, methyl-cyclopentane, cyclopentane, methyl-cyclohexane, butyl-cyclohexane, and pentyl-cyclohexane. In an example, the combine amount of aromatic and cyclic species can be at most 100%.

In some embodiments, the crude fuel mixture comprises alkenes. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of at least about 0.1 wt %, about 0.5 wt %, about 1 wt %, about 2 wt %, about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, or about 30 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of at most about 30 wt %, about 25 wt %, about 20 wt %, about 15 wt %, about 10 wt %, about 5 wt %, about 2 wt %, about 1 wt %, about 0.5 wt %, or about 0.1 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of from about 0.1 wt % to about 30 wt %, about 0.5 wt % to about 30 wt %, about 0.5 wt % to about 25 wt %, about 1 wt % to about 25 wt %, about 0.1 wt % to about 15 wt %, about 1 wt % to about 15 wt %, or about 2 wt % to about 20 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of about 0.1 wt %, about 0.5 wt %, about 1 wt %, about 2 wt %, about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, or about 30 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of from about 0.01 wt % to about 30 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of at least 0.01 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of at most 4 wt %. In some embodiments, the crude fuel mixture comprises the alkenes in an amount of from about 0.01 wt % to about 4 wt %. Non-limiting examples of alkenes include 3-nonene, 4-nonene, and 2-nonene.

In some embodiments, the crude fuel mixture comprises oxygenated species. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of at least about 0.1 wt %, about 0.5 wt %, about 1 wt %, about 2 wt %, about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, or about 30 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of at most about 30 wt %, about 25 wt %, about 20 wt %, about 15 wt %, about 10 wt %, about 5 wt %, about 2 wt %, about 1 wt %, about 0.5 wt %, or about 0.1 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of from about 0.1 wt % to about 30 wt %, about 0.5 wt % to about 30 wt %, about 0.5 wt % to about 25 wt %, about 1 wt % to about 25 wt %, about 0.1 wt % to about 15 wt %, about 1 wt % to about 15 wt %, or about 2 wt % to about 20 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of about 0.1 wt %, about 0.5 wt %, about 1 wt %, about 2 wt %, about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, or about 30 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of from about 0.01 wt % to about 30 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of at least 0.01 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of at most 4 wt %. In some embodiments, the crude fuel mixture comprises the oxygenated species in an amount of from about 0.01 wt % to about 4 wt %. Non-limiting examples of oxygenated species include 4-butyl phenol and decanoic acid.

In some embodiments, the hydrocarbons in the crude fuel mixture comprise an average carbon number of from about 7 to about 10. In some embodiments, the hydrocarbons in the crude fuel mixture comprise an average carbon number of from about 8 to about 9.

In some embodiments, the methods provided herein comprise purifying the crude fuel mixture (e.g., resulting from the processing of the composition comprising one or more of the substituted or unsubstituted lactones and lipids) to produce a sustainable fuel. The sustainable fuel may be any sustainable fuel as described herein, such as a sustainable aviation fuel, a renewable diesel, a renewable naphtha, or a sustainable light fuel.

The crude fuel mixture may comprise any combination of light products, aviation fuel, and diesel fuel, or any of the components of said fuels. In some embodiments, the sustainable fuel comprises sustainable aviation fuel (SAF), renewable diesel, renewable naphtha, (sustainable) light fuel, or a combination thereof. In some embodiments, the sustainable fuel comprises purified and separated: SAF, renewable diesel, renewable naphtha, and sustainable light fuel.

In some embodiments, the sustainable fuel comprises SAF in an amount of at least 30 wt % (e.g., relative to the total amount of SAF, renewable diesel, renewable naphtha, and sustainable light fuel present in the sustainable fuel before separation). In some embodiments, the sustainable fuel comprises SAF in an amount of at least about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, or about 75 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of at most about 75 wt %, about 70 wt %, about 65 wt %, about 60 wt %, about 55 wt %, about 50 wt %, about 45 wt %, about 40 wt %, about 35 wt %, or about 30 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of about 30 wt % to about 75 wt %, about 35 wt % to about 70 wt %, about 50 wt % to about 70 wt %, about 55 wt % to about 65 wt %, about 40 wt % to about 60 wt %, or about 50 wt % to about 60 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, or about 75 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of at least 40 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of at least 50 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of from about 40 wt % to about 70 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of about 60 wt %. In some embodiments, the sustainable fuel comprises SAF in an amount of about 58 wt %.

In some embodiments, the sustainable fuel comprises renewable diesel in an amount of at least 10 wt % (e.g., relative to the total amount of SAF, renewable diesel, renewable naphtha, and sustainable light fuel present in the sustainable fuel before separation). In some embodiments, the sustainable fuel comprises renewable diesel in an amount of at least about 2 wt %, about 5 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 25 wt %, about 30 wt %, or about 35 wt %. In some embodiments, the sustainable fuel comprises renewable diesel in an amount of at most about 35 wt %, about 30 wt %, about 25 wt %, about 20 wt %, about 18 wt %, about 15 wt %, about 12 wt %, about 10 wt %, about 5 wt %, or about 2 wt %. In some embodiments, the sustainable fuel comprises renewable diesel in an amount of about 2 wt % to about 35 wt %, about 5 wt % to about 30 wt %, about 15 wt % to about 30 wt %, about 18 wt % to about 25 wt %, about 10 wt % to about 20 wt %, or about 15 wt % to about 20 wt %. In some embodiments, the sustainable fuel comprises renewable diesel in an amount of about 2 wt %, about 5 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 25 wt %, about 30 wt %, or about 35 wt %. In some embodiments, the sustainable fuel comprises renewable diesel in an amount of from about 10 wt % to about 30 wt %. In some embodiments, the sustainable fuel comprises renewable diesel in an amount of about 20 wt %.

In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of at least 10 wt % (e.g., relative to the total amount of SAF, renewable diesel, renewable naphtha, and sustainable light fuel present in the sustainable fuel before separation). In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of at least about 5 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, or about 40 wt %. In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of at most about 40 wt %, about 35 wt %, about 30 wt %, about 25 wt %, about 20 wt %, about 18 wt %, about 15 wt %, about 12 wt %, about 10 wt %, or about 5 wt %. In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of about 5 wt % to about 40 wt %, about 10 wt % to about 35 wt %, about 18 wt % to about 35 wt %, about 20 wt % to about 30 wt %, about 12 wt % to about 25 wt %, or about 18 wt % to about 25 wt %. In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of about 5 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, or about 40 wt %. In some embodiments, the sustainable fuel comprises sustainable renewable naphtha in an amount of about 25 wt %. %. In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of from about 10 wt % to about 30 wt %.

In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of at least 10 wt % (e.g., relative to the total amount of SAF, renewable diesel, renewable naphtha, and sustainable light fuel present in the sustainable fuel before separation). In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of at least about 5 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, or about 40 wt %. In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of at most about 40 wt %, about 35 wt %, about 30 wt %, about 25 wt %, about 20 wt %, about 18 wt %, about 15 wt %, about 12 wt %, about 10 wt %, or about 5 wt %. In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of about 5 wt % to about 40 wt %, about 10 wt % to about 35 wt %, about 18 wt % to about 35 wt %, about 20 wt % to about 30 wt %, about 12 wt % to about 25 wt %, or about 18 wt % to about 25 wt %. In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of about 5 wt %, about 10 wt %, about 12 wt %, about 15 wt %, about 18 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, or about 40 wt %. In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of about 25 wt %. %. In some embodiments, the sustainable fuel comprises sustainable light fuel in an amount of from about 10 wt % to about 30 wt %.

In some embodiments, the sustainable fuel comprises SAF in an amount of from about 40 wt % to about 70 wt %, renewable diesel in an amount of from about 10 wt % to about 30 wt %, renewable naphtha in an amount of from about 10 wt % to about 30 wt %, and light fuel in an amount of from about 10 wt % to about 30 wt % (e.g., relative to the total amount of SAF, renewable diesel, renewable naphtha, and sustainable light fuel present in the sustainable fuel before separation). In some embodiments, the sustainable fuel comprises SAF in an amount of from about 50 wt % to about 60 wt %, renewable diesel in an amount of from about 15 wt % to about 25 wt %, renewable naphtha in an amount of from about 15 wt % to about 25 wt %, and light fuel in an amount of from about 15 wt % to about 25 wt % (e.g., relative to the total amount of SAF, renewable diesel, and sustainable light fuel present in the sustainable fuel before separation). In some embodiments, the sustainable fuel comprises SAF in an amount of from about 65 wt % to about 85 wt %, renewable diesel in an amount from about 2 wt % to about 10 wt %, renewable naphtha in an amount from about 5 wt % to about 20 wt %, and light fuel in an amount from about 2 wt % to about 10 wt %.

In some embodiments, the sustainable fuel can be produced by the methods herein in an amount of at least 100 L, at least 1000 L, or at least 10000 L. In some embodiments, the SAF can be produced by the methods herein in an amount of at least 100 L, at least 1000 L, or at least 10000 L. In some embodiments, the renewable diesel can be produced by the methods herein in an amount of at least 100 L, at least 1000 L, or at least 10000 L. In some embodiments, the renewable naphtha can be produced by the methods herein in an amount of at least 100 L, at least 1000 L, or at least 10000 L. In some embodiments, the sustainable light fuel can be produced by the methods herein in an amount of at least 100 L, at least 1000 L, or at least 10000 L.

In some embodiments, the method further comprises combusting the light fuel and recovering the waste heat. In some embodiments, the method further comprises combusting the renewable naphtha and recovering the waste heat. In some embodiments, the method further comprises combusting the renewable diesel and recovering the waste heat. In some embodiments, the waste heat is recycled to the method described herein.

In some embodiments, purifying comprises fractionation. The fractionating may comprise use of a reboiler and a condenser. The fractionating may be completed at about 1 atm.

In some embodiments, the reboiler may be operated at any suitable temperature. In some embodiments, the reboiler comprises a temperature of at least 200° C. In some embodiments, the reboiler comprises a temperature of at least about 200° C., about 210° C., about 220° C., about 230° C., about 240° C., about 250° C., about 260° C., about 270° C., about 280° C., or about 300° C. In some embodiments, the reboiler comprises a temperature of at most about 300° C., about 280° C., about 270° C., about 260° C., about 250° C., about 240° C., about 230° C., about 220° C., about 210° C., or about 200° C. In some embodiments, the reboiler comprises a temperature of about 200° C. to about 300° C., about 210° C. to about 280° C., about 230° C. to about 270° C., about 240° C. to about 260° C., about 210° C. to about 250° C., or about 230° C. to about 250° C. In some embodiments, the reboiler comprises a temperature of about 200° C., about 210° C., about 220° C., about 230° C., about 240° C., about 250° C., about 260° C., about 270° C., about 280° C., or about 300° C. In some embodiments, the reboiler comprises a temperature of from about 200° C. to about 300° C. In some embodiments, the reboiler comprises a temperature of about 250° C.

In some embodiments, the condenser may be operated at any suitable temperature. In some embodiments, the condenser comprises a temperature of at least 50° C. In some embodiments, the condenser comprises a temperature of at least about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., about 70° C., about 75° C., about 80° C., about 85° C., or about 90° C. In some embodiments, the condenser comprises a temperature of at most about 90° C., about 85° C., about 80° C., about 75° C., about 70° C., about 65° C., about 60° C., about 55° C., about 50° C., or about 45° C. In some embodiments, the condenser comprises a temperature of about 45° C. to about 90° C., about 50° C. to about 85° C., about 60° C. to about 80° C., about 65° C. to about 75° C., about 65° C. to about 75° C., about 50° C. to about 70° C., or about 60° C. to about 70° C. In some embodiments, the condenser comprises a temperature of about 45° C., about 50° C., about 55° C., about 60° C., about 65° C., about 70° C., about 75° C., about 80° C., about 85° C., or about 90° C. In some embodiments, the condenser comprises a temperature of 50° C. to about 90° C. In some embodiments, the condenser comprises a temperature of about 70° C.

In some embodiments, the sustainable fuel herein comprises a reduced carbon intensity (CI) than that of other fuels prepared by other methods in the art. In some embodiments, the sustainable fuel (e.g., SAF or renewable diesel) comprises a CI of less than 50 g CO₂e/MJ. In some embodiments, the sustainable fuel (e.g., SAF or renewable diesel) comprises of CI of less than 45 g CO₂e/MJ, 40 g CO₂e/MJ, 35 g CO₂e/MJ, 30 g CO₂e/MJ, 25 g CO₂e/MJ, 20 g CO₂e/MJ, or 15 g CO₂e/MJ. In some embodiments, the sustainable fuel (e.g., SAF or renewable diesel) comprises a CI of from 1 g CO₂e/MJ to about 50 g CO₂e/MJ, from about 5 g CO₂e/MJ to about 40 g CO₂e/MJ, from about 10 g CO₂e/MJ to about 40 g CO₂e/MJ or from about 10 g CO₂e/MJ to about 40 g CO₂e/MJ. In some embodiments, CI is measured using the R&D GREET 2024 model (e.g., as described at http://greet.anl.gov/). In some embodiments, the sustainable fuel (e.g. SAF or renewable diesel) comprises a CI of less than 0 g CO₂e/MJ

In some embodiments, the SAF herein comprises a reduced carbon intensity (CI) than that of other fuels prepared by other methods in the art. In some embodiments, the SAF comprises a CI of less than 50 g CO₂e/MJ. In some embodiments, the SAF comprises of CI of less than 45 g CO₂e/MJ, 40 g CO₂e/MJ, 35 g CO₂e/MJ, 30 g CO₂e/MJ, 25 g CO₂e/MJ, 20 g CO₂e/MJ, or 15 g CO₂e/MJ. In some embodiments, the SAF comprises a CI of from 1 g CO₂e/MJ to about 50 g CO₂e/MJ, from about 5 g CO₂e/MJ to about 40 g CO₂e/MJ, from about 10 g CO₂e/MJ to about 40 g CO₂e/MJ or from about 10 g CO₂e/MJ to about 40 g CO₂e/MJ. In some embodiments, the SAF comprises a CI of less than 35 g CO₂e/MJ. In some embodiments, the SAF comprises a CI of less than 20 g CO₂e/MJ. In some embodiments, CI is measured using the R&D GREET 2024 model (e.g., as described at http://greet.anl.gov/). In some embodiments, the SAF comprises a CI of less than 0 g CO₂e/MJ.

In some instances, the methods provided herein produce sustainable fuels at a lower cost than methods using other feedstocks (e.g., not using the lactones or one or more lipids provided herein). In some instances, the methods provided herein produce SAF at a lower cost than methods using other feedstocks (e.g., not using the lactones or one or more lipids provided herein).

In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 40% lower than the cost of producing aviation fuel using HEFA and oilseed oil as a feedstock. In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 50% lower than the cost of producing aviation fuel using HEFA and oilseed oil as a feedstock. In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 60% lower than the cost of producing aviation fuel using HEFA and oilseed oil as a feedstock.

In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 5% lower than the cost of producing aviation fuel using HEFA and palm oil as a feedstock. In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 10% lower than the cost of producing aviation fuel using HEFA and palm oil as a feedstock. In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 15% lower than the cost of producing aviation fuel using HEFA and palm oil as a feedstock. In some embodiments, a cost of producing the SAF (e.g., by using the methods provided herein) is at least 20% lower than the cost of producing aviation fuel using HEFA and palm oil as a feedstock.

Sustainable Aviation Fuel

The methods provided herein may be used to produce sustainable aviation fuel (SAF). The sustainable aviation fuel may satisfy the Jet Fuel A specification (e.g., sustainable Jet Fuel A) or the Jet Fuel A-1 specification (e.g., sustainable Jet Fuel A-1). In some embodiments, the sustainable aviation fuel satisfies the Jet Fuel A specification (e.g., sustainable Jet Fuel A). In some embodiments, the sustainable aviation fuel satisfies Jet Fuel A-1 specification (e.g., sustainable Jet Fuel A-1).

In some embodiments, the produced SAF is blended with conventional/fossil-based jet fuel and may satisfy the Jet Fuel A-1 specification or the Jet Fuel A specification. In some embodiments, the produced SAF is blended at a 1:1 ratio with conventional/fossil-based jet fuel. In some instances, the produced SAF is blended at a 1:20 ratio with conventional/fossil-based jet fuel. In some instances, the produced SAF is blended at a 1:50 ratio with conventional/fossil-based jet fuel. In some instances, the produced SAF is blended at a ratio of 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20, 1:25, 1:30, 1:35, 1:40, 1:45, or 1:50 with conventional/fossil based jet fuel

In some embodiments, the SAF comprises deoxygenated hydrocarbons, naphthenes, aromatics, or a combination thereof.

In some embodiments, the SAF comprises C₈-C₁₆ deoxygenated hydrocarbons. In some embodiments the SAF comprises a combination of C₈-C₁₀ deoxygenated hydrocarbons, C₁₁-C₁₃ deoxygenated hydrocarbons, and C₁₄-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the SAF comprises C₈-C₁₀ deoxygenated hydrocarbons. In some embodiments, the SAF comprises C₈-C₁₀ deoxygenated hydrocarbons in an amount of at least about 70 wt %, 75 wt %, 80 wt %, 85 wt %, 90 wt %, 95 wt %, 100 wt %. In some embodiments, the SAF comprises C₈-C₁₀ deoxygenated hydrocarbons in an amount of at most about 95 wt %, about 94 wt %, about 93 wt %, about 92 wt %, about 91 wt %, about 90 wt %, about 89 wt %, about 88 wt %, about 87 wt %, about 86 wt %, about 85 wt %, about 84 wt %, about 83 wt %, about 82 wt %, about 81 wt %, about 80 wt %, about 79 wt %, about 78 wt %, about 77 wt %, about 76 wt %, about 75 wt %, about 74 wt %, about 73 wt %, about 72 wt %, about 71 wt % or about 70 wt %. In some embodiments, the SAF comprises C₈-C₁₀ deoxygenated hydrocarbons in an amount of from about 70 wt % to about 100 wt %. In some embodiments, the SAF comprises C₈-C₁₀ deoxygenated hydrocarbons in an amount of about 70 wt %. In some embodiments, the wt % of C₈-C₁₀deoxygenated hydrocarbons is relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the SAF comprises C₁₁-C₁₃ deoxygenated hydrocarbons. In some embodiments, the SAF comprises C₁₁-C₁₃ deoxygenated hydrocarbons in an amount of at least about 0.5 wt %, about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, about 10 wt %, about 11 wt %, about 12 wt %, about 13 wt %, about 14 wt %, or about 15 wt %. In some embodiments, the SAF comprises C₁₁-C₁₃ deoxygenated hydrocarbons in an amount of at most about 15 wt %, about 14 wt %, about 13 wt %, about 12 wt %, about 11 wt %, about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, about 3 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the SAF comprises C₁₁-C₁₃ deoxygenated hydrocarbons in an amount of less than about 15 wt %. In some embodiments, the SAF comprises C₁₀-C₁₄ deoxygenated hydrocarbons in an amount of from about 0.5 wt % to about 15 wt %. In some embodiments, the SAF comprises C₁₁-C₁₃ deoxygenated hydrocarbons in an amount of about 70 wt %. In some embodiments, the wt % of C₁₁-C₁₃ deoxygenated hydrocarbons is relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the SAF comprises C₁₄-C₁₆ deoxygenated hydrocarbons. In some embodiments, the SAF comprises C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of at least about 0.5 wt %, about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, about 10 wt %, about 11 wt %, about 12 wt %, about 13 wt %, about 14 wt %, or about 15 wt %. In some embodiments, the SAF comprises C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of at most about 15 wt %, about 14 wt %, about 13 wt %, about 12 wt %, about 11 wt %, about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, about 3 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the SAF comprises C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of from about 0.5 wt % to about 15 wt %. In some embodiments, the SAF comprises C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of less than about 15 wt %. In some embodiments, the SAF comprises C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of about 15 wt %. In some embodiments, the wt % of C₁₄-C₁₆ deoxygenated hydrocarbons is relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the SAF comprises one or more impurities. The impurities may comprise sulfur, nitrogen, phosphorus, potassium, magnesium, calcium, sodium, iron, aluminum, silicon, organic chlorides, free fatty acids, or a combination thereof.

In some embodiments, the SAF comprises sulfur. In some embodiments, the SAF comprises sulfur in an amount of from about 10 ppm to about 50 ppm. In some embodiments, the SAF comprises sulfur in an amount of at least about 5 ppm, about 10 ppm, about 15 ppm, about 20 ppm, about 25 ppm, about 30 ppm, about 35 ppm, about 40 ppm, about 45 ppm, or about 50 ppm. In some embodiments, the SAF comprises sulfur in an amount of at most about 50 ppm, about 45 ppm, about 40 ppm, about 35 ppm, about 30 ppm, about 25 ppm, about 20 ppm, about 15 ppm, about 10 ppm, or about 5 ppm. In some embodiments, the SAF comprises sulfur in an amount of about 5 ppm to about 50 ppm, about 10 ppm to about 45 ppm, about 25 ppm to about 45 ppm, about 30 ppm to about 40 ppm, about 15 ppm to about 35 ppm, or about 25 ppm to about 35 ppm. In some embodiments, the SAF comprises sulfur in an amount of about 5 ppm, about 10 ppm, about 15 ppm, about 20 ppm, about 25 ppm, about 30 ppm, about 35 ppm, about 40 ppm, about 45 ppm, or about 50 ppm. In some embodiments, the SAF comprises sulfur in an amount of no more than 40 ppm. In some embodiments, the SAF comprises sulfur in an amount of at least 10 ppm.

In some embodiments, the SAF comprises nitrogen. In some embodiments, the SAF comprises nitrogen in an amount of from about 50 ppm to about 100 ppm. In some embodiments, the SAF comprises nitrogen in an amount of at least about 55 ppm, about 60 ppm, about 65 ppm, about 70 ppm, about 75 ppm, about 80 ppm, about 85 ppm, about 90 ppm, about 95 ppm, or about 100 ppm. In some embodiments, the SAF comprises nitrogen in an amount of at most about 100 ppm, about 95 ppm, about 90 ppm, about 85 ppm, about 80 ppm, about 75 ppm, about 70 ppm, about 65 ppm, about 60 ppm, or about 55 ppm. In some embodiments, the SAF comprises nitrogen in an amount of about 55 ppm to about 100 ppm, about 60 ppm to about 95 ppm, about 70 ppm to about 90 ppm, about 75 ppm to about 85 ppm, about 60 ppm to about 80 ppm, or about 70 ppm to about 80 ppm. In some embodiments, the SAF comprises nitrogen in an amount of about 55 ppm, about 60 ppm, about 65 ppm, about 70 ppm, about 75 ppm, about 80 ppm, about 85 ppm, about 90 ppm, about 95 ppm, or about 100 ppm. In some embodiments, the SAF comprises nitrogen in an amount of from about 80 ppm to about 90 ppm. In some embodiments, the SAF comprises nitrogen in an amount of no more than 100 ppm. In some embodiments, the SAF comprises nitrogen in an amount of at least 50 ppm.

In some embodiments, the SAF comprises phosphorus. In some embodiments, the SAF comprises phosphorus in an amount of from about 0.01 ppm to about 2 ppm. In some embodiments, the SAF comprises phosphorus in an amount of at least about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.3 ppm, about 0.5 ppm, about 1 ppm, about 1.5 ppm, or about 2 ppm. In some embodiments, the SAF comprises phosphorus in an amount of at most about 2 ppm, about 1.5 ppm, about 1 ppm, about 0.5 ppm, about 0.3 ppm, about 0.2 ppm, about 0.15 ppm, about 0.1 ppm, about 0.05 ppm, or about 0.01 ppm. In some embodiments, the SAF comprises phosphorus in an amount of about 0.01 ppm to about 2 ppm, about 0.05 ppm to about 1.5 ppm, about 0.1 ppm to about 0.5 ppm, about 0.15 ppm to about 0.3 ppm, about 0.2 ppm to about 1.5 ppm, or about 0.2 ppm to about 0.5 ppm. In some embodiments, the SAF comprises phosphorus in an amount of about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.3 ppm, about 0.5 ppm, about 1 ppm, about 1.5 ppm, or about 2 ppm. In some embodiments, the SAF comprises phosphorus in an amount of from about 0.1 ppm to about 0.3 ppm. In some embodiments, the SAF comprises phosphorus in an amount of no more than 1 ppm.

In some embodiments, the SAF comprises potassium. In some embodiments, the SAF comprises potassium in an amount of from about 0.5 ppm to about 3 ppm. In some embodiments, the SAF comprises potassium in an amount of at least about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the SAF comprises potassium in an amount of at most about 3 ppm, about 2.5 ppm, about 2.2 ppm, about 2 ppm, about 1.6 ppm, about 1.4 ppm, about 1.2 ppm, about 1 ppm, about 0.8 ppm, or about 0.5 ppm. In some embodiments, the SAF comprises potassium in an amount of about 0.5 ppm to about 3 ppm, about 0.8 ppm to about 2.5 ppm, about 1 ppm to about 2 ppm, about 1.2 ppm to about 1.6 ppm, about 1.4 ppm to about 2.5 ppm, or about 1.4 ppm to about 2 ppm. In some embodiments, the SAF comprises potassium in an amount of about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the SAF comprises potassium in an amount of less than 2 ppm. In some embodiments, the SAF comprises potassium in an amount of from about 1 ppm to about 2 ppm.

In some embodiments, the SAF comprises magnesium. In some embodiments, the SAF comprises magnesium in an amount of from about 0.5 ppm to about 3 ppm. In some embodiments, the SAF comprises magnesium in an amount of at least about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the SAF comprises magnesium in an amount of at most about 3 ppm, about 2.5 ppm, about 2.2 ppm, about 2 ppm, about 1.6 ppm, about 1.4 ppm, about 1.2 ppm, about 1 ppm, about 0.8 ppm, or about 0.5 ppm. In some embodiments, the SAF comprises magnesium in an amount of about 0.5 ppm to about 3 ppm, about 0.8 ppm to about 2.5 ppm, about 1 ppm to about 2 ppm, about 1.2 ppm to about 1.6 ppm, about 1.4 ppm to about 2.5 ppm, or about 1.4 ppm to about 2 ppm. In some embodiments, the SAF comprises magnesium in an amount of about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the SAF comprises magnesium in an amount of less than 2 ppm. In some embodiments, the SAF comprises magnesium in an amount of from about 1 ppm to about 2 ppm.

In some embodiments, the SAF comprises calcium. In some embodiments, the SAF comprises calcium in an amount of from about 1 ppm to about 5 ppm. In some embodiments, the SAF comprises calcium in an amount of at least about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the SAF comprises calcium in an amount of at most about 5.5 ppm, about 5 ppm, about 4.5 ppm, about 4 ppm, about 3.5 ppm, about 3 ppm, about 2.5 ppm, about 2 ppm, about 1.5 ppm, or about 1 ppm. In some embodiments, the SAF comprises calcium in an amount of about 1 ppm to about 5.5 ppm, about 1.5 ppm to about 5 ppm, about 2 ppm to about 4 ppm, about 2.5 ppm to about 3.5 ppm, about 3 ppm to about 5 ppm, or about 3 ppm to about 4 ppm. In some embodiments, the SAF comprises calcium in an amount of about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the SAF comprises calcium in an amount of less than 5 ppm. In some embodiments, the SAF comprises calcium in an amount of from about 3 ppm to about 4 ppm.

In some embodiments, the SAF comprises sodium. In some embodiments, the SAF comprises sodium in an amount of from about 3 ppm to about 8 ppm. In some embodiments, the SAF comprises sodium in an amount of at least about 0.5 ppm, about 1 ppm, about 2 ppm, about 3 ppm, about 4 ppm, about 5 ppm, about 6 ppm, about 7 ppm, about 8 ppm, or about 9 ppm. In some embodiments, the SAF comprises sodium in an amount of at most about 9 ppm, about 8 ppm, about 7 ppm, about 6 ppm, about 5 ppm, about 4 ppm, about 3 ppm, about 2 ppm, about 1 ppm, or about 0.5 ppm. In some embodiments, the SAF comprises sodium in an amount of about 0.5 ppm to about 9 ppm, about 1 ppm to about 8 ppm, about 3 ppm to about 7 ppm, about 4 ppm to about 6 ppm, about 1 ppm to about 5 ppm, or about 3 ppm to about 5 ppm. In some embodiments, the SAF comprises sodium in an amount of about 0.5 ppm, about 1 ppm, about 2 ppm, about 3 ppm, about 4 ppm, about 5 ppm, about 6 ppm, about 7 ppm, about 8 ppm, or about 9 ppm. In some embodiments, the SAF comprises the sodium in an amount of from about 5 ppm to about 6 ppm. In some embodiments, the SAF comprises the sodium in an amount of less than about 6 ppm.

In some embodiments, the SAF comprises iron. In some embodiments, the SAF comprises iron in an amount of from about 0.05 ppm to about 0.5 ppm. In some embodiments, the SAF comprises iron in an amount of at least about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.4 ppm, about 0.5 ppm, or about 0.6 ppm. In some embodiments, the SAF comprises iron in an amount of at most about 0.6 ppm, about 0.5 ppm, about 0.4 ppm, about 0.3 ppm, about 0.25 ppm, about 0.2 ppm, about 0.15 ppm, about 0.1 ppm, about 0.05 ppm, or about 0.01 ppm. In some embodiments, the SAF comprises iron in an amount of about 0.01 ppm to about 0.6 ppm, about 0.05 ppm to about 0.5 ppm, about 0.1 ppm to about 0.3 ppm, about 0.15 ppm to about 0.25 ppm, about 0.2 ppm to about 0.5 ppm, or about 0.2 ppm to about 0.3 ppm. In some embodiments, the SAF comprises iron in an amount of about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.4 ppm, about 0.5 ppm, or about 0.6 ppm. In some embodiments, the SAF comprises iron in an amount of from about 0.1 ppm to about 0.3 ppm. In some embodiments, the SAF comprises iron in an amount of less than about 0.3 ppm.

In some embodiments, the SAF comprises aluminum. In some embodiments, the SAF comprises aluminum in an amount of from about 0.1 ppm to about 0.5 ppm. In some embodiments, the SAF comprises aluminum in an amount of at least about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.35 ppm, about 0.4 ppm, about 0.45 ppm, or about 0.5 ppm. In some embodiments, the SAF comprises aluminum in an amount of at most about 0.5 ppm, about 0.45 ppm, about 0.4 ppm, about 0.35 ppm, about 0.3 ppm, about 0.25 ppm, about 0.2 ppm, about 0.15 ppm, about 0.1 ppm, or about 0.05 ppm. In some embodiments, the SAF comprises aluminum in an amount of about 0.05 ppm to about 0.5 ppm, about 0.1 ppm to about 0.45 ppm, about 0.2 ppm to about 0.4 ppm, about 0.25 ppm to about 0.35 ppm, about 0.1 ppm to about 0.3 ppm, or about 0.2 ppm to about 0.3 ppm. In some embodiments, the SAF comprises aluminum in an amount of about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.35 ppm, about 0.4 ppm, about 0.45 ppm, or about 0.5 ppm. In some embodiments, the SAF comprises aluminum in an amount of from about 0.1 ppm to about 0.4 ppm. In some embodiments, the SAF comprises aluminum in an amount of less than about 0.4 ppm.

In some embodiments, the SAF comprises silicon. In some embodiments, the SAF comprises silicon in an amount of from about 1 ppm to about 5 ppm. In some embodiments, the SAF comprises silicon in an amount of at least about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the SAF comprises silicon in an amount of at most about 5.5 ppm, about 5 ppm, about 4.5 ppm, about 4 ppm, about 3.5 ppm, about 3 ppm, about 2.5 ppm, about 2 ppm, about 1.5 ppm, or about 1 ppm. In some embodiments, the SAF comprises silicon in an amount of about 1 ppm to about 5.5 ppm, about 1.5 ppm to about 5 ppm, about 2.5 ppm to about 4.5 ppm, about 3 ppm to about 4 ppm, about 1.5 ppm to about 3.5 ppm, or about 2.5 ppm to about 3.5 ppm. In some embodiments, the SAF comprises silicon in an amount of about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the SAF comprises silicon in an amount of from about 3 ppm to about 4 ppm. In some embodiments, the SAF comprises silicon in an amount of less than about 4 ppm.

In some embodiments, the SAF comprises organic chlorides. In some embodiments, the SAF comprises organic chlorides in an amount of at most about 3 ppm, about 2.5 ppm, about 2 ppm, about 1.5 ppm, about 1.2 ppm, about 1 ppm, about 0.7 ppm, about 0.5 ppm, about 0.2 ppm, or about 0.1 ppm. In some embodiments, the SAF comprises organic chloride in an amount of less than 1 ppm.

In some embodiments, the SAF comprises free fatty acids. In some embodiments, the free fatty acids comprise one or more of (C22:0) behenic acid, (C18:3) linolenic acid, (C24:0) lignoceric acid, (C18:1) oleic acid, and <C14:0 fatty acids.

In some embodiments, the SAF comprises behenic acid. In some embodiments, the SAF comprises behenic acid in an amount of at most about 75 wt %, about 70 wt %, about 65 wt %, about 60 wt %, about 55 wt %, about 50 wt %, about 45 wt %, about 40 wt %, about 35 wt %, or about 30 wt %. In some embodiments, the wt % of behenic acid is relative to the total amount of free fatty acids.

In some embodiments, the SAF comprises linolenic acid. In some embodiments, the SAF comprises linolenic acid in an amount of at most about 35 wt %, about 30 wt %, about 17 wt %, about 25 wt %, about 22 wt %, about 20 wt %, about 17 wt %, about 15 wt %, about 12 wt %, or about 10 wt %. In some embodiments, the wt % of linolenic acid is relative to the total amount of free fatty acids.

In some embodiments, the SAF comprises lignoceric acid. In some embodiments, the SAF comprises lignoceric acid in an amount of at most about 35 wt %, about 30 wt %, about 17 wt %, about 25 wt %, about 22 wt %, about 20 wt %, about 17 wt %, about 15 wt %, about 12 wt %, or about 10 wt %. In some embodiments, the wt % of lignoceric acid is relative to the total amount of free fatty acids.

In some embodiments, the SAF comprises oleic acid. In some embodiments, the SAF comprises oleic acid in an amount of at most about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, about 3 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the wt % of oleic acid is relative to the total amount of free fatty acids.

In some embodiments, the SAF comprises <C₁₄ fatty acids (e.g., fatty acids of carbon chain length less than 14). In some embodiments, the SAF comprises <C₁₄ fatty acids in an amount of at most about 5 wt %, about 4 wt %, about 3.5 wt %, about 3 wt %, about 2.5 wt %, about 2 wt %, about 1.5 wt %, about 1 wt %, about 0.5 wt %, or about 0.1 wt %. In some embodiments, the wt % of <C₁₄ fatty acids is relative to the total amount of free fatty acids.

Renewable Diesel

The methods provided herein may be used to produce renewable diesel. The renewable diesel may be diesel #1 (e.g., renewable diesel #1). The renewable diesel may be diesel #2 (e.g., renewable diesel #2).

In some embodiments, the renewable diesel comprises deoxygenated hydrocarbons, naphthenes, aromatics, or a combination thereof.

In some embodiments, the renewable diesel comprises C₁₆-C₂₂ deoxygenated hydrocarbons, such as paraffins, naphthenes, aromatics, cycloparaffins, arenes, or combinations thereof. In some embodiments the renewable diesel comprises a combination of C₁₆-C₁₈ deoxygenated hydrocarbons, C₁₉-C₂₀ deoxygenated hydrocarbons, and C₂₁-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons, such as paraffins, naphthene, aromatics, cycloparaffins, arenes, or combinations thereof. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of from about 40 wt % to about 70 wt %. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of at least about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, or about 80 wt %. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of at most about 80 wt %, about 75 wt %, about 70 wt %, about 65 wt %, about 60 wt %, about 55 wt %, about 50 wt %, about 45 wt %, about 40 wt %, or about 35 wt %. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of about 35 wt % to about 80 wt %, about 40 wt % to about 75 wt %, about 40 wt % to about 60 wt %, about 45 wt % to about 55 wt %, about 50 wt % to about 70 wt %, or about 50 wt % to about 60 wt %. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, or about 80 wt %. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of less than 70 wt %. In some embodiments, the renewable diesel comprises C₁₆-C₁₈ deoxygenated hydrocarbons in an amount to about 50 wt %. In some embodiments, the wt % of C₁₆-C₁₈ deoxygenated hydrocarbons is relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of less than 40 wt %. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of at least about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, or about 50 wt %. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of at most about 50 wt %, about 45 wt %, about 40 wt %, about 35 wt %, about 30 wt %, about 25 wt %, about 20 wt %, about 15 wt %, about 10 wt %, or about 5 wt %. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of about 5 wt % to about 50 wt %, about 10 wt % to about 45 wt %, about 15 wt % to about 35 wt %, about 20 wt % to about 30 wt %, about 25 wt % to about 45 wt %, or about 25 wt % to about 35 wt %. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, or about 50 wt %. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of from about 15 wt % to about 40 wt %. In some embodiments, the renewable diesel comprises C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of about 25 wt %. In some embodiments, the wt % of C₁₉-C₂₀ deoxygenated hydrocarbons is relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of less than 40 wt %. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of at least about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, or about 50 wt %. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of at most about 50 wt %, about 45 wt %, about 40 wt %, about 35 wt %, about 30 wt %, about 25 wt %, about 20 wt %, about 15 wt %, about 10 wt %, or about 5 wt %. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of about 5 wt % to about 50 wt %, about 10 wt % to about 45 wt %, about 15 wt % to about 35 wt %, about 20 wt % to about 30 wt %, about 25 wt % to about 45 wt %, or about 25 wt % to about 35 wt %. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, or about 50 wt %. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of from about 15 wt % to about 40 wt %. In some embodiments, the renewable diesel comprises C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of about 25 wt %. In some embodiments, the wt % of C₂₁-C₂₂ deoxygenated hydrocarbons is relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the renewable diesel comprises one or more impurities. The impurities may comprise sulfur, nitrogen, phosphorus, potassium, magnesium, calcium, sodium, iron, aluminum, silicon, organic chlorides, free fatty acids, or a combination thereof.

In some embodiments, the renewable diesel comprises sulfur. In some embodiments, the renewable diesel comprises sulfur in an amount of from about 10 ppm to about 50 ppm. In some embodiments, the renewable diesel comprises sulfur in an amount of at least about 5 ppm, about 10 ppm, about 15 ppm, about 20 ppm, about 25 ppm, about 30 ppm, about 35 ppm, about 40 ppm, about 45 ppm, or about 50 ppm. In some embodiments, the renewable diesel comprises sulfur in an amount of at most about 50 ppm, about 45 ppm, about 40 ppm, about 35 ppm, about 30 ppm, about 25 ppm, about 20 ppm, about 15 ppm, about 10 ppm, or about 5 ppm. In some embodiments, the renewable diesel comprises sulfur in an amount of about 5 ppm to about 50 ppm, about 10 ppm to about 45 ppm, about 25 ppm to about 45 ppm, about 30 ppm to about 40 ppm, about 15 ppm to about 35 ppm, or about 25 ppm to about 35 ppm. In some embodiments, the renewable diesel comprises sulfur in an amount of about 5 ppm, about 10 ppm, about 15 ppm, about 20 ppm, about 25 ppm, about 30 ppm, about 35 ppm, about 40 ppm, about 45 ppm, or about 50 ppm. In some embodiments, the renewable diesel comprises sulfur in an amount of no more than 40 ppm. In some embodiments, the renewable diesel comprises sulfur in an amount of at least 10 ppm.

In some embodiments, the renewable diesel comprises nitrogen. In some embodiments, the renewable diesel comprises nitrogen in an amount of from about 50 ppm to about 100 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of at least about 55 ppm, about 60 ppm, about 65 ppm, about 70 ppm, about 75 ppm, about 80 ppm, about 85 ppm, about 90 ppm, about 95 ppm, or about 100 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of at most about 100 ppm, about 95 ppm, about 90 ppm, about 85 ppm, about 80 ppm, about 75 ppm, about 70 ppm, about 65 ppm, about 60 ppm, or about 55 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of about 55 ppm to about 100 ppm, about 60 ppm to about 95 ppm, about 70 ppm to about 90 ppm, about 75 ppm to about 85 ppm, about 60 ppm to about 80 ppm, or about 70 ppm to about 80 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of about 55 ppm, about 60 ppm, about 65 ppm, about 70 ppm, about 75 ppm, about 80 ppm, about 85 ppm, about 90 ppm, about 95 ppm, or about 100 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of from about 80 ppm to about 90 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of no more than 100 ppm. In some embodiments, the renewable diesel comprises nitrogen in an amount of at least 50 ppm.

In some embodiments, the renewable diesel comprises phosphorus. In some embodiments, the renewable diesel comprises phosphorus in an amount of from about 0.01 ppm to about 2 ppm. In some embodiments, the renewable diesel comprises phosphorus in an amount of at least about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.3 ppm, about 0.5 ppm, about 1 ppm, about 1.5 ppm, or about 2 ppm. In some embodiments, the renewable diesel comprises phosphorus in an amount of at most about 2 ppm, about 1.5 ppm, about 1 ppm, about 0.5 ppm, about 0.3 ppm, about 0.2 ppm, about 0.15 ppm, about 0.1 ppm, about 0.05 ppm, or about 0.01 ppm. In some embodiments, the renewable diesel comprises phosphorus in an amount of about 0.01 ppm to about 2 ppm, about 0.05 ppm to about 1.5 ppm, about 0.1 ppm to about 0.5 ppm, about 0.15 ppm to about 0.3 ppm, about 0.2 ppm to about 1.5 ppm, or about 0.2 ppm to about 0.5 ppm. In some embodiments, the renewable diesel comprises phosphorus in an amount of about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.3 ppm, about 0.5 ppm, about 1 ppm, about 1.5 ppm, or about 2 ppm. In some embodiments, the renewable diesel comprises phosphorus in an amount of from about 0.1 ppm to about 0.3 ppm. In some embodiments, the renewable diesel comprises phosphorus in an amount of no more than 1 ppm.

In some embodiments, the renewable diesel comprises potassium. In some embodiments, the renewable diesel comprises potassium in an amount of from about 0.5 ppm to about 3 ppm. In some embodiments, the renewable diesel comprises potassium in an amount of at least about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the renewable diesel comprises potassium in an amount of at most about 3 ppm, about 2.5 ppm, about 2.2 ppm, about 2 ppm, about 1.6 ppm, about 1.4 ppm, about 1.2 ppm, about 1 ppm, about 0.8 ppm, or about 0.5 ppm. In some embodiments, the renewable diesel comprises potassium in an amount of about 0.5 ppm to about 3 ppm, about 0.8 ppm to about 2.5 ppm, about 1 ppm to about 2 ppm, about 1.2 ppm to about 1.6 ppm, about 1.4 ppm to about 2.5 ppm, or about 1.4 ppm to about 2 ppm. In some embodiments, the renewable diesel comprises potassium in an amount of about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the renewable diesel comprises potassium in an amount of less than 2 ppm. In some embodiments, the renewable diesel comprises potassium in an amount of from about 1 ppm to about 2 ppm.

In some embodiments, the renewable diesel comprises magnesium. In some embodiments, the renewable diesel comprises magnesium in an amount of from about 0.5 ppm to about 3 ppm. In some embodiments, the renewable diesel comprises magnesium in an amount of at least about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the renewable diesel comprises magnesium in an amount of at most about 3 ppm, about 2.5 ppm, about 2.2 ppm, about 2 ppm, about 1.6 ppm, about 1.4 ppm, about 1.2 ppm, about 1 ppm, about 0.8 ppm, or about 0.5 ppm. In some embodiments, the renewable diesel comprises magnesium in an amount of about 0.5 ppm to about 3 ppm, about 0.8 ppm to about 2.5 ppm, about 1 ppm to about 2 ppm, about 1.2 ppm to about 1.6 ppm, about 1.4 ppm to about 2.5 ppm, or about 1.4 ppm to about 2 ppm. In some embodiments, the renewable diesel comprises magnesium in an amount of about 0.5 ppm, about 0.8 ppm, about 1 ppm, about 1.2 ppm, about 1.4 ppm, about 1.6 ppm, about 2 ppm, about 2.2 ppm, about 2.5 ppm, or about 3 ppm. In some embodiments, the renewable diesel comprises magnesium in an amount of less than 2 ppm. In some embodiments, the renewable diesel comprises magnesium in an amount of from about 1 ppm to about 2 ppm.

In some embodiments, the renewable diesel comprises calcium. In some embodiments, the renewable diesel comprises calcium in an amount of from about 1 ppm to about 5 ppm. In some embodiments, the renewable diesel comprises calcium in an amount of at least about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the renewable diesel comprises calcium in an amount of at most about 5.5 ppm, about 5 ppm, about 4.5 ppm, about 4 ppm, about 3.5 ppm, about 3 ppm, about 2.5 ppm, about 2 ppm, about 1.5 ppm, or about 1 ppm. In some embodiments, the renewable diesel comprises calcium in an amount of about 1 ppm to about 5.5 ppm, about 1.5 ppm to about 5 ppm, about 2 ppm to about 4 ppm, about 2.5 ppm to about 3.5 ppm, about 3 ppm to about 5 ppm, or about 3 ppm to about 4 ppm. In some embodiments, the renewable diesel comprises calcium in an amount of about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the renewable diesel comprises calcium in an amount of less than 5 ppm. In some embodiments, the renewable diesel comprises calcium in an amount of from about 3 ppm to about 4 ppm.

In some embodiments, the renewable diesel comprises sodium. In some embodiments, the renewable diesel comprises sodium in an amount of from about 3 ppm to about 8 ppm. In some embodiments, the renewable diesel comprises sodium in an amount of at least about 0.5 ppm, about 1 ppm, about 2 ppm, about 3 ppm, about 4 ppm, about 5 ppm, about 6 ppm, about 7 ppm, about 8 ppm, or about 9 ppm. In some embodiments, the renewable diesel comprises sodium in an amount of at most about 9 ppm, about 8 ppm, about 7 ppm, about 6 ppm, about 5 ppm, about 4 ppm, about 3 ppm, about 2 ppm, about 1 ppm, or about 0.5 ppm. In some embodiments, the renewable diesel comprises sodium in an amount of about 0.5 ppm to about 9 ppm, about 1 ppm to about 8 ppm, about 3 ppm to about 7 ppm, about 4 ppm to about 6 ppm, about 1 ppm to about 5 ppm, or about 3 ppm to about 5 ppm. In some embodiments, the renewable diesel comprises sodium in an amount of about 0.5 ppm, about 1 ppm, about 2 ppm, about 3 ppm, about 4 ppm, about 5 ppm, about 6 ppm, about 7 ppm, about 8 ppm, or about 9 ppm. In some embodiments, the renewable diesel comprises the sodium in an amount of from about 5 ppm to about 6 ppm. In some embodiments, the renewable diesel comprises the sodium in an amount of less than about 6 ppm.

In some embodiments, the renewable diesel comprises iron. In some embodiments, the renewable diesel comprises iron in an amount of from about 0.05 ppm to about 0.5 ppm. In some embodiments, the renewable diesel comprises iron in an amount of at least about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.4 ppm, about 0.5 ppm, or about 0.6 ppm. In some embodiments, the renewable diesel comprises iron in an amount of at most about 0.6 ppm, about 0.5 ppm, about 0.4 ppm, about 0.3 ppm, about 0.25 ppm, about 0.2 ppm, about 0.15 ppm, about 0.1 ppm, about 0.05 ppm, or about 0.01 ppm. In some embodiments, the renewable diesel comprises iron in an amount of about 0.01 ppm to about 0.6 ppm, about 0.05 ppm to about 0.5 ppm, about 0.1 ppm to about 0.3 ppm, about 0.15 ppm to about 0.25 ppm, about 0.2 ppm to about 0.5 ppm, or about 0.2 ppm to about 0.3 ppm. In some embodiments, the renewable diesel comprises iron in an amount of about 0.01 ppm, about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.4 ppm, about 0.5 ppm, or about 0.6 ppm. In some embodiments, the renewable diesel comprises iron in an amount of from about 0.1 ppm to about 0.3 ppm. In some embodiments, the renewable diesel comprises iron in an amount of less than about 0.3 ppm.

In some embodiments, the renewable diesel comprises aluminum. In some embodiments, the renewable diesel comprises aluminum in an amount of from about 0.1 ppm to about 0.5 ppm. In some embodiments, the renewable diesel comprises aluminum in an amount of at least about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.35 ppm, about 0.4 ppm, about 0.45 ppm, or about 0.5 ppm. In some embodiments, the renewable diesel comprises aluminum in an amount of at most about 0.5 ppm, about 0.45 ppm, about 0.4 ppm, about 0.35 ppm, about 0.3 ppm, about 0.25 ppm, about 0.2 ppm, about 0.15 ppm, about 0.1 ppm, or about 0.05 ppm. In some embodiments, the renewable diesel comprises aluminum in an amount of about 0.05 ppm to about 0.5 ppm, about 0.1 ppm to about 0.45 ppm, about 0.2 ppm to about 0.4 ppm, about 0.25 ppm to about 0.35 ppm, about 0.1 ppm to about 0.3 ppm, or about 0.2 ppm to about 0.3 ppm. In some embodiments, the renewable diesel comprises aluminum in an amount of about 0.05 ppm, about 0.1 ppm, about 0.15 ppm, about 0.2 ppm, about 0.25 ppm, about 0.3 ppm, about 0.35 ppm, about 0.4 ppm, about 0.45 ppm, or about 0.5 ppm. In some embodiments, the renewable diesel comprises aluminum in an amount of from about 0.1 ppm to about 0.4 ppm. In some embodiments, the renewable diesel comprises aluminum in an amount of less than about 0.4 ppm.

In some embodiments, the renewable diesel comprises silicon. In some embodiments, the renewable diesel comprises silicon in an amount of from about 1 ppm to about 5 ppm. In some embodiments, the renewable diesel comprises silicon in an amount of at least about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the renewable diesel comprises silicon in an amount of at most about 5.5 ppm, about 5 ppm, about 4.5 ppm, about 4 ppm, about 3.5 ppm, about 3 ppm, about 2.5 ppm, about 2 ppm, about 1.5 ppm, or about 1 ppm.

In some embodiments, the renewable diesel comprises silicon in an amount of about 1 ppm to about 5.5 ppm, about 1.5 ppm to about 5 ppm, about 2.5 ppm to about 4.5 ppm, about 3 ppm to about 4 ppm, about 1.5 ppm to about 3.5 ppm, or about 2.5 ppm to about 3.5 ppm. In some embodiments, the renewable diesel comprises silicon in an amount of about 1 ppm, about 1.5 ppm, about 2 ppm, about 2.5 ppm, about 3 ppm, about 3.5 ppm, about 4 ppm, about 4.5 ppm, about 5 ppm, or about 5.5 ppm. In some embodiments, the renewable diesel comprises silicon in an amount of from about 3 ppm to about 4 ppm. In some embodiments, the renewable diesel comprises silicon in an amount of less than about 4 ppm.

In some embodiments, the renewable diesel comprises organic chlorides. In some embodiments, the renewable diesel comprises organic chlorides in an amount of at most about 3 ppm, about 2.5 ppm, about 2 ppm, about 1.5 ppm, about 1.2 ppm, about 1 ppm, about 0.7 ppm, about 0.5 ppm, about 0.2 ppm, or about 0.1 ppm. In some embodiments, the renewable diesel comprises organic chlorides in an amount of less than 1 ppm.

In some embodiments, the renewable diesel comprises free fatty acids. In some embodiments, the free fatty acids comprise one or more of (C22:0) behenic acid, (C18:3) linolenic acid, (C24:0) lignoceric acid, (C18:1) oleic acid, and <C14:0 fatty acids.

In some embodiments, the renewable diesel comprises behenic acid. In some embodiments, the renewable diesel comprises behenic acid in an amount of from about 40 wt % to about 60 wt % (e.g., relative to the total amount of free fatty acids). In some embodiments, the renewable diesel comprises behenic acid in an amount of at least about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, or about 75 wt %. In some embodiments, the renewable diesel comprises behenic acid in an amount of at most about 75 wt %, about 70 wt %, about 65 wt %, about 60 wt %, about 55 wt %, about 50 wt %, about 45 wt %, about 40 wt %, about 35 wt %, or about 30 wt %. In some embodiments, the renewable diesel comprises behenic acid in an amount of about 30 wt % to about 75 wt %, about 35 wt % to about 70 wt %, about 40 wt % to about 60 wt %, about 45 wt % to about 55 wt %, about 50 wt % to about 70 wt %, or about 50 wt % to about 60 wt %. In some embodiments, the renewable diesel comprises behenic acid in an amount of about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, or about 75 wt %. In some embodiments, the wt % of behenic acid is relative to the total amount of free fatty acids.

In some embodiments, the renewable diesel comprises linolenic acid. In some embodiments, the renewable diesel comprises linolenic acid in an amount of from about 10 wt % to about 30 wt % (e.g., relative to the total amount of free fatty acids). In some embodiments, the renewable diesel comprises linolenic acid in an amount of at least about 10 wt %, about 12 wt %, about 15 wt %, about 17 wt %, about 20 wt %, about 22 wt %, about 25 wt %, about 17 wt %, about 30 wt %, or about 35 wt %. In some embodiments, the renewable diesel comprises linolenic acid in an amount of at most about 35 wt %, about 30 wt %, about 17 wt %, about 25 wt %, about 22 wt %, about 20 wt %, about 17 wt %, about 15 wt %, about 12 wt %, or about 10 wt %. In some embodiments, the renewable diesel comprises linolenic acid in an amount of about 10 wt % to about 35 wt %, about 12 wt % to about 30 wt %, about 17 wt % to about 17 wt %, about 20 wt % to about 25 wt %, about 12 wt % to about 22 wt %, or about 17 wt % to about 22 wt %. In some embodiments, the renewable diesel comprises linolenic acid in an amount of about 10 wt %, about 12 wt %, about 15 wt %, about 17 wt %, about 20 wt %, about 22 wt %, about 25 wt %, about 17 wt %, about 30 wt %, or about 35 wt %. In some embodiments, the wt % of linolenic acid is relative to the total amount of free fatty acids.

In some embodiments, the renewable diesel comprises lignoceric acid. In some embodiments, the renewable diesel comprises lignoceric acid in an amount of from about 10 wt % to about 25 wt % (e.g., relative to the total amount of free fatty acids). In some embodiments, the renewable diesel comprises lignoceric acid in an amount of at least about 10 wt %, about 12 wt %, about 15 wt %, about 17 wt %, about 20 wt %, about 22 wt %, about 25 wt %, about 17 wt %, about 30 wt %, or about 35 wt %. In some embodiments, the renewable diesel comprises lignoceric acid in an amount of at most about 35 wt %, about 30 wt %, about 17 wt %, about 25 wt %, about 22 wt %, about 20 wt %, about 17 wt %, about 15 wt %, about 12 wt %, or about 10 wt %. In some embodiments, the renewable diesel comprises lignoceric acid in an amount of about 10 wt % to about 35 wt %, about 12 wt % to about 30 wt %, about 12 wt % to about 22 wt %, about 15 wt % to about 20 wt %, about 17 wt % to about 17 wt %, or about 17 wt % to about 22 wt %. In some embodiments, the renewable diesel comprises lignoceric acid in an amount of about 10 wt %, about 12 wt %, about 15 wt %, about 17 wt %, about 20 wt %, about 22 wt %, about 25 wt %, about 17 wt %, about 30 wt %, or about 35 wt %. In some embodiments, the wt % of lignoceric acid is relative to the total amount of free fatty acids.

In some embodiments, the renewable diesel comprises oleic acid. In some embodiments, the renewable diesel comprises oleic acid in an amount of from about 1 wt % to about 10 wt % (e.g., relative to the total amount of free fatty acids). In some embodiments, the renewable diesel comprises oleic acid in an amount of at least about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt %. In some embodiments, the renewable diesel comprises oleic acid in an amount of at most about 10 wt %, about 9 wt %, about 8 wt %, about 7 wt %, about 6 wt %, about 5 wt %, about 4 wt %, about 3 wt %, about 2 wt %, or about 1 wt %. In some embodiments, the renewable diesel comprises oleic acid in an amount of about 1 wt % to about 10 wt %, about 2 wt % to about 9 wt %, about 3 wt % to about 7 wt %, about 4 wt % to about 6 wt %, about 5 wt % to about 9 wt %, or about 5 wt % to about 7 wt %. In some embodiments, the renewable diesel comprises oleic acid in an amount of about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt %. In some embodiments, the wt % of oleic acid is relative to the total amount of free fatty acids.

In some embodiments, the renewable diesel comprises <C₁₄ fatty acids (e.g., fatty acids of carbon chain length less than 14). In some embodiments, the renewable diesel comprises <C₁₄ fatty acids in an amount of from about 0.1 wt % to about 5 wt % (e.g., relative to the total amount of free fatty acids). In some embodiments, the renewable diesel comprises <C₁₄ fatty acids in an amount of at least about 0.1 wt %, about 0.5 wt %, about 1 wt %, about 1.5 wt %, about 2 wt %, about 2.5 wt %, about 3 wt %, about 3.5 wt %, about 4 wt %, or about 5 wt %. In some embodiments, the renewable diesel comprises <C₁₄ fatty acids in an amount of at most about 5 wt %, about 4 wt %, about 3.5 wt %, about 3 wt %, about 2.5 wt %, about 2 wt %, about 1.5 wt %, about 1 wt %, about 0.5 wt %, or about 0.1 wt %. In some embodiments, the renewable diesel comprises <C₁₄ fatty acids in an amount of about 0.1 wt % to about 5 wt %, about 0.5 wt % to about 4 wt %, about 1 wt % to about 3 wt %, about 1.5 wt % to about 2.5 wt %, about 2 wt % to about 4 wt %, or about 2 wt % to about 3 wt %. In some embodiments, the renewable diesel comprises <C₁₄ fatty acids in an amount of about 0.1 wt %, about 0.5 wt %, about 1 wt %, about 1.5 wt %, about 2 wt %, about 2.5 wt %, about 3 wt %, about 3.5 wt %, about 4 wt %, or about 5 wt %. In some embodiments, the wt % of <C₁₄ fatty acids is relative to the total amount of free fatty acids.

While preferred embodiments of the present disclosure have been shown and described herein, it will be obvious to those skilled in the art that such embodiments are provided by way of example only. Numerous variations, changes, and substitutions will now occur to those skilled in the art without departing from the disclosure. It should be understood that various alternatives to the embodiments of the disclosure described herein may be employed in practicing the disclosure. It is intended that the following claims define the scope of the disclosure and that methods and structures within the scope of these claims and their equivalents be covered thereby.

EXAMPLES

The following examples are provided to further illustrate some embodiments of the present disclosure but are not intended to limit the scope of the disclosure; it will be understood by their exemplary nature that other procedures, methodologies, or techniques known to those skilled in the art may alternatively be used.

Example 1: Method of Preparing Sustainable Fuels from Bio-Derived Lipids

In Example 1, sustainable fuels were prepared from bio-derived lipids according to the following process.

Here, heavy oil, a mixture of lipids described by Formula (I-A) and Formula (I-B), and shown in Table 1, was produced via fermentation of A. pullulans in an aerobic environment utilizing xylose, glucose, sucrose, and arabinose among other carbon sources. The heavy oil product has a mannitol headgroup, and a chain of three hydroxylated decanoic acid molecules. The complete fermentation design includes feed holding tanks, fermentation broth holding tanks, process cooling, vent gas scrubber, and the CIP system. The heavy oil was purified via solvent extraction with methyl ethyl ketone and the solvent was removed through vacuum distillation and centrifugation.

The purified heavy oil was then fed into a bench-scale packed-bed reactor which was packed with solid catalyst in order to conduct both hydrotreating and isomerization/cracking.

Hydrotreatment and isomerization/cracking of the purified heavy oil occurred over numerous operating conditions and using a variety of solid catalysts, several of which are described below. Generally, the purified heavy oil was fed at a rate of about 1.5-12 mL/hr, and this feed stream was heated to 60-80° C. to aid flow. The reactor was held at an elevated pressure of about 30-60 bar, and an elevated temperature of about 325-400° C. After reacting over the catalyst bed, liquid products were collected and analyzed via gas chromatography-mass spectrometry (GC/MS).

In one instance, similar to Example 1, Ni/SAPO-11 was used as the catalyst at 350° C. and 40 bar, and the resulting mixture of products (average carbon number=8.5) is summarized in Table 2A and 2B.

TABLE 2A
wt %	Species

38.8%	nonane
8.5%	3-nonene
5.6%	4-nonene
4.2%	MEK
3.7%	2-nonene
3.5%	4-butyl-phenol
2.5%	h eptane
2.1%	p entane
1.9%	2-nonene
1.7%	h exane
1.4%	decanoic acid
1.3%	pentyl-cyclopentane
1.1%	1,5-diisopropyl-2,3-dimethyl-cyclohexane
1.1%	1-nonene
0.9%	o ctane

TABLE 2B
wt %	Species

0.78%	Alkanes (C>14)
41.41%	Alkanes (C9-C14)
7.92%	Alkanes (C<9)
3.00%	Aromatic species
5.90%	Cyclic species
25.53%	Alkenes
15.47%	Oxygenated species

In one instance, Pt/SAPO-11 was used as the catalyst at 350° C. and 40 bar, and the resulting mixture of products (average carbon number=9) is summarized in Table 3A and 3B.

TABLE 3A
wt %	Species

64.74%	n onane
4.25%	4-methyl octane
2.93%	h eptane
2.52%	3-methyl octane
2.25%	pentane
2.06%	hexane
1.26%	3-nonene
1.08%	methyl-cyclopentane
1.02%	2-butyl phenol
0.74%	butyl benzene
0.67%	4-nonene
0.62%	decane
0.61%	2,5-dimethyl heptane
0.59%	2-nonene
0.58%	propyl-benzene

TABLE 3B
wt %	Species

1.11%	Alkanes (C>14)
74.00%	Alkanes (C9-C14)
8.90%	Alkanes (C<9)
6.73%	Aromatic species
2.66%	Cyclic species
3.10%	Alkenes
3.50%	Oxygenated species

In one instance, Pt/SAPO-11 was used as the catalyst at 375° C. and 40 bar, and the resulting mixture of products (average carbon number=8.4) is summarized in Table 4A and 4B.

TABLE 4A
wt %	Species

58.50%	nonane
5.45%	pentane
4.28%	4-methyl octane
3.45%	butane
3.01%	heptane
2.59%	3-methyl octane
2.21%	hexane
1.33%	methyl-cyclopentane
1.05%	2-methyl butane
0.92%	benzene
0.84%	propyl-benzene
0.78%	butyl-benzene
0.77%	2-methyl pentane
0.69%	cyclopentane
0.67%	toluene

TABLE 4B
wt %	Species

0.66%	Alkanes (C>14)
68.38%	Alkanes (C9-C14)
17.41%	Alkanes (C<9)
7.20%	Aromatic species
2.80%	Cyclic species
1.20%	Alkenes
2.40%	Oxygenated species

In another instance, 5% Pd/C was used as a catalyst at 375° C. and 40 bar, and the resulting mixture of products (average carbon number=8.4) is summarized in Table 5A and 5B.

TABLE 5A
wt %	Species

64.97%	nonane
6.00%	heptane
5.26%	hexane
4.75%	pentane
1.89%	toluene
1.65%	2,4-dimethyl hexane
1.61%	butane
1.38%	4-methyl octane
1.17%	butyl benzene
1.04%	benzene
0.85%	ethylbenzene
0.81%	propyl-benzene
0.80%	3-methyl octane
0.65%	1,2,4,5-tetrahydronaphthalene
0.64%	naphthalene

TABLE 5B
wt %	Species

0.00%	Alkanes (C>14)
68.40%	Alkanes (C9-C14)
19.26%	Alkanes (C<9)
9.80%	Aromatic species
2.50%	Cyclic species
0.10%	Alkenes
0.00%	Oxygenated species

In one instance, 5% Pd/C was used as the catalyst at 350° C. and 40 bar, and the resulting mixture of products after 18 hours on-stream (average carbon number=8.6) is summarized in Table 6A and 6B.

TABLE 6A
wt %	Species

77.09%	nonane
3.90%	heptane
3.79%	pentane
2.80%	hexane
2.06%	butane
1.02%	butyl-cyclohexane
0.85%	decane
0.75%	pentyl-cyclohexane
0.67%	octane
0.65%	undecane
0.46%	1-ethyl-2-methyl benzene
0.40%	cyclohexane
0.39%	methyl-cyclohexane
0.33%	methyl-cyclopentane
0.32%	toluene

TABLE 6B
wt %	Species

0.22%	Alkanes (C>14)
79.52%	Alkanes (C9-C14)
13.22%	Alkanes (C<9)
2.70%	Aromatic species
4.20%	Cyclic species
0.00%	Alkenes
0.10%	Oxygenated species

For the same instance using 5% Pd/C at 350° C. and 40 bar, the resulting mixture of products after 26 hours on-stream (average carbon number=8.7) is summarized in Table 7A and 7B, and the resulting mixture of products after 42 hours on-stream (average carbon number=8.8) is summarized in Table 8A and 8B.

TABLE 7A
wt %	Species

79.94%	nonane
3.56%	heptane
3.02%	pentane
2.48%	hexane
1.43%	butane
1.30%	butyl-cyclohexane
0.81%	decane
0.81%	pentyl-cyclohexane
0.68%	undecane
0.62%	octane
0.48%	cyclohexane
0.38%	methyl-cyclopentane
0.36%	methyl-cyclohexane
0.31%	pentadecane
0.30%	decahydro-naphthalene

TABLE 7B
wt %	Species

0.37%	Alkanes (C>14)
82.11%	Alkanes (C9-C14)
11.11%	Alkanes (C<9)
1.80%	Aromatic species
4.50%	Cyclic species
0.00%	Alkenes
0.20%	Oxygenated species

TABLE 8A
wt %	Species

79.00%	nonane
3.45%	heptane
2.81%	pentane
2.47%	hexane
2.02%	butyl-cyclohexane
1.12%	pentyl-cyclohexane
1.03%	butane
0.76%	decane
0.69%	undecane
0.68%	octane
0.67%	cyclohexane
0.43%	methyl-cyclopentane
0.37%	methyl-cyclohexane
0.35%	pentadecane
0.30%	heptylcyclohexane

TABLE 8B
wt %	Species

0.44%	Alkanes (C>14)
81.00%	Alkanes (C9-C14)
10.44%	Alkanes (C<9)
1.90%	Aromatic species
5.80%	Cyclic species
0.00%	Alkenes
0.40%	Oxygenated species

In Example 1, in one instance, 5% Pd/C was used as the catalyst at 350° C. and 60 bar, and the resulting mixture of products (average carbon number=8.7) is summarized in Table 9A and 9B. Notably, significantly more cyclic products were produced at this elevated pressure as compared to 40 bar.

TABLE 9A
wt %	Species

62.41%	nonane
9.03%	butyl-cyclohexane
5.81%	heptane
4.93%	pentane
2.86%	hexane
2.33%	butane
1.33%	decane
1.32%	Pentyl-cyclohexane
1.11%	undecane
1.02%	octane
0.78%	cyclohexane
0.61%	methyl-cyclopentane
0.59%	methyl-cyclohexane
0.51%	pentadecane
0.48%	decahydro-naphthalene

TABLE 9B
wt %	Species

0.61%	Alkanes (C>14)
67.58%	Alkanes (C9-C14)
16.95%	Alkanes (C<9)
0.80%	Aromatic species
13.80%	Cyclic species
0.00%	Alkenes
0.30%	Oxygenated species

In one instance, Mo₂C was used as the catalyst at 350° C. and 40 bar, and the resulting mixture of products (average carbon number=8.5) is summarized in Table 10A and 10B. Notably, significantly more C10 hydrocarbons were produced with this catalyst as compared to Pt/SAPO-11 and 5% Pd/C.

TABLE 10A
wt %	Species

38.85%	nonane
13.16%	decane
11.86%	butane
8.17%	hexane
3.18%	butyl-cyclohexane
3.18%	butyl-benzene
2.65%	pentane
2.63%	octane
1.61%	heptane
1.20%	methyl-cyclopentane
1.10%	2,4-diisopropyl-1,1-dimethyl cyclohexane
1.04%	undecane
0.79%	cyclohexane
0.72%	propane
0.32%	propyl cyclohexane

TABLE 10B
wt %	Species

0.94%	Alkanes (C>14)
54.92%	Alkanes (C9-C14)
27.64%	Alkanes (C<9)
5.11%	Aromatic species
8.20%	Cyclic species
1.27%	Alkenes
1.90%	Oxygenated species

Example 2: Blending Bio-Derived SAF with Conventional Jet Fuel

Sustainable fuels were prepared as described in Example 1. After liquid products were collected, they were blended with conventional fossil-based Jet-A fuel at sustainable fuel: Jet-A mass ratios of 1:9 and 1:19. Samples were thoroughly mixed and analyzed via simulated distillation (SimDist). SimDist curves for the conventional jet fuel as well as the above-described blends are shown in FIG. 5.

FIG. 5 depicts simulated distillation curves for conventional Jet-A (solid), 10% sustainable fuel/90% conventional Jet-A (dashed), and 5% sustainable fuel/95% conventional Jet-A (dotted).

Example 3: Method of Preparing Sustainable Aviation Fuel and Renewable Diesel

In Example 3, Sustainable aviation fuel and renewable diesel may be prepared according to the scheme in FIG. 1 and FIG. 2.

Sustainable aviation fuel and renewable diesel were prepared according to the following process (101, 203). Mannitol and a mixture of 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone were provided (102). The estimated flow of mannitol and lactones was about 847 kg/h. To the reactor, hydrogen (103, 208) was added along with distillers corn oil (DCO) (104, 209). The estimated flow of DCO was about 847 kg/h. The mixture was reacted at about 340° C. and 30 bar to produce deoxygenated hydrocarbons, carbon dioxide, carbon monoxide, and water via hydrogenation, hydrodeoxygenation, dehydration, decarboxylation, and decarbonylation reactions. This reaction took place in the presence of a Mo₂C/Al₂O₃ catalyst. The products of the reaction were separated in a flash drum at 165° C. and 20 bar and the resulting hydrocarbons were fed to the isomerization and cracking reactor. In the isomerization and cracking step, the hydrocarbons were partially cracked and isomerized to a diverse mix of products, as described in Tables 10A & 10B.

The resulting mix of products were fractionated to produce a renewable diesel cut (106, 211), a SAF cut (107, 212), and a sustainable light fuel cut (108, 213). The estimated production of aviation fuel was about 754 kg/h. The estimated production of diesel was about 267 kg/h. The estimated production of light fuels was about 347 kg/h. Overall estimated mass yields per kg of oil fed to the reactor are about 0.45 kg aviation fuel/kg oil, 0.2 kg light fuels/kg oil, 0.16 kg diesel/kg oil, and 0.21 kg H₂O/kg oil. The remainder of the output comprises carbon dioxide.

Example 4: Method of Preparing Lactone Mixture

In Example 4, heavy oil was produced via fermentation of A. pullulans in an aerobic environment utilizing xylose, glucose, sucrose, and arabinose among other carbon sources. The heavy oil product has a mannitol headgroup, and a chain of three hydroxylated decanoic acid molecules. The complete fermentation design includes feed holding tanks, fermentation broth holding tanks, process cooling, vent gas scrubber, and the CIP system.

The resulting crude heavy oil was processed via the downstream processing block. The downstream processing block includes a Coflore liquid-liquid extraction unit, a water stripper distillation column, and a two liquid phase decanter system. In this system, fermentation broth is counter-currently exposed to MEK solvent (205), preferentially extracting the heavy oil product. An extract phase, saturated in water but enriched in the heavy oil was sent to the distillation block. The raffinate phase, deficient in the heavy oil, contained the cells and other water-soluble components. The raffinate was sent to the stripping column (reboiler operated at 100° C. and condenser operated at 73° C.), where any remaining MEK is stripped from the system before the water stream is discharged for wastewater treatment (206). Recycled MEK and water are mixed and allowed to settle in the decanter (operated at 40° C.). The aqueous and organic phases are immiscible, and are separated before being recycled to the stripper and liquid-liquid extraction units respectively.

The mass flow of the fermentation broth is about 17,693 kg/h and the solvent to fermentation broth ratio is about 0.5. The flow rate of the extract leaving this block is about 8705 kg/h and contains about 99.95 wt % of the heavy oil product.

Distillation Route A. The heavy oil product was saponified in sodium hydroxide. A 12:1 base: oil molar ratio was utilized. The saponification was completed at about 30° C. followed by lactonization in dilute mineral acid (e.g., sulfuric acid or hydrochloric acid at pH of about 2.5). The lactonization steps occurred at about 150° C. Following lactonization, the sample was neutralized with 9% NaHCO₃/H₂O for a total of three washes. This results in a crude lactone product which is about 50 wt % lactones, as measured by GC-MS.

The crude lactone product was then further purified via vacuum distillation, which took place at less than 200° C. under vacuum (pressure <10 mbar). The distillation resulted in the production of the lactone products, 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone.

Distillation Route B. The heavy oil product was acidified in concentration mineral acid (e.g., sulfuric acid or hydrochloric acid) at a pH of about 0. The acidification took place at a temperature of about 150° C. This was followed by vacuum distillation at less than 200° C. under vacuum (pressure <10 mbar). The distillation resulted in the production of the lactone products, 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone.

Distillation Route (′. The heavy oil product was saponified in a strong base, such as potassium hydroxide or sodium hydroxide. The saponification was completed at about 40° C. After saponification, thermal lactonization of the saponified heavy oil was completed at a temperature of greater than 250° C. in the absence of an acid catalyst, followed by (or concurrently) distilling the lactone products, 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone.

In each distillation route, the resulting stream was sent to the fuel production block. The flow rate of the heavy oil to the distillation block is about 888 kg/h. The estimated conversion efficacy is about 1% conversion to residue, 4% conversion to water, 24% conversion to mannitol, and 71% conversion to lactones.

The resulting lactones are used in the process described in Example 3.

Additional Embodiments

The following exemplary embodiments are provided, the order of which is not to be construed as designating levels of importance:

Provided herein, in some embodiments, is a method of preparing a sustainable fuel, the method comprising:

• • (a) providing a composition, wherein the composition comprises:
    • one or more substituted or unsubstituted lactones, one or more lipids represented by a structure of Formula (I), or a combination thereof;

• • • wherein,
      • R¹ is hydrogen (H) or COCH₃;
      • R² is 1 to 10 O-acylated 3,5-dihydroxydecanoate or 3,5-dihydroxydodecanoate groups;
      • R³ is L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; and
      • R⁴ is C₅-C₇ alkyl;
  • (b) processing the composition to produce a crude fuel mixture; and
  • (c) purifying the crude fuel mixture to provide the sustainable fuel.

In some embodiments, the composition comprises one or more substituted or unsubstituted lactones.

In some embodiments, the composition comprises one or more substituted or unsubstituted saturated or unsaturated lactones.

In some embodiments, the composition comprises one or more substituted saturated or unsaturated lactones.

In some embodiments, the composition comprises one or more saturated or

unsaturated lactones substituted with one or more of C₁-C₈ alkyl and hydroxyl.

In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-δ-lactone.

In some embodiments, the composition comprises 3,5-dihydroxydecanoic acid-δ-lactone.

In some embodiments, the composition comprises 5-hydroxy-2-decenoic acid-δ-lactone and 3,5-dihydroxydecanoic acid-δ-lactone.

In some embodiments, R² is 1 to 10 O-acylated 3,5-dihydroxydecanoate ester groups.

In some embodiments, R⁴ is C₅ alkyl or C₇ alkyl.

In some embodiments, R¹ is L- or D-mannitol, L- or D-glycerol, or L- or D-arabitol.

In some embodiments, the one or more lipids comprise:

or a combination thereof.

In some embodiments, the processing comprises hydrotreatment, product separation, isomerization, cracking, or a combination thereof.

In some embodiments, the processing does not comprise deodorization, neutralization, degumming, bleaching, or a combination thereof.

In some embodiments, the hydrotreatment comprises use of a catalyst.

In some embodiments, the isomerization and/or cracking comprise use of a catalyst.

In some embodiments, the catalyst is a sulfide, carbide, phosphide, or nanoparticle of Pd, Pt, Ni, Ru, Mo, Co, Ag, Cu, Sn, W, Rh, Au, Ir, Fe or a combination thereof.

In some embodiments, the catalyst is CoMoS_x, NiMoS_x, WS₂, MoS₂, MoC, Mo₂C_<9 or a combination thereof.

In some embodiments, the hydrotreatment comprises use of a catalyst support.

In some embodiments, the isomerization and/or cracking comprise use of a catalyst support.

In some embodiments, the catalyst support comprises carbon, a metal oxide, a zeolite, a zeotype, or a combination thereof.

In some embodiments, the metal oxide is TiO₂, Al₂O₃, SiO₂, ZrO₂, or CeO₂.

In some embodiments, the zeolite is beta zeolite, faujasite, mordenite, ZSM-5, ZSM-22, or ZSM-23.

In some embodiments, the zeotype is SAPO-11, SAPO-5, or SAPO-34.

In some embodiments, the hydrotreatment comprises use of a NiMo sulfide/Al₂O₃ catalyst.

In some embodiments, the isomerization and/or cracking comprises use of a Pt/SAPO-11, Ni/SAPO-11, of Pd/C catalyst.

In some embodiments, the hydrotreatment is completed at a temperature of at least 250° C.

In some embodiments, the hydrotreatment is completed at a temperature of at least 300° C.

In some embodiments, the hydrotreatment is completed at a temperature of from about 300° C. to about 400° C.

In some embodiments, the hydrotreatment is completed at a temperature of from about 320° C. to about 360° C.

In some embodiments, the isomerization and/or cracking is completed at a temperature of at least 250° C.

In some embodiments, the isomerization and/or cracking is completed at a temperature of at least 300° C.

In some embodiments, the isomerization and/or cracking is completed at a temperature of from about 300° C. to about 400° C.

In some embodiments, the isomerization and/or cracking is completed at a temperature of from about 320° C. to about 360° C.

In some embodiments, the product separation comprises flash evaporation.

In some embodiments, the flash evaporation comprises use of a flash drum at a temperature of from about 150° C. to about 180°.

In some embodiments, the purifying comprises fractionation.

In some embodiments, the fractionation comprises use of a reboiler and a condenser.

In some embodiments, the reboiler comprises a temperature of at least 200° C.

In some embodiments, the reboiler comprises a temperature of from about 200° C. to about 300° C.

In some embodiments, the condenser comprises a temperature of at least 50° C.

In some embodiments, the condenser comprises a temperature of from about 50° C. to about 90° C.

In some embodiments, the hydrotreatment is completed at a pressure of at least 10 atm.

In some embodiments, the hydrotreatment is completed at a pressure of at least 20 atm.

In some embodiments, the hydrotreatment is completed at a pressure of from about 10 atm to about 300 atm.

In some embodiments, the isomerization and/or cracking is completed at a pressure of at least 5 atm.

In some embodiments, the isomerization and/or cracking is completed at a pressure of at least 10 atm.

In some embodiments, the isomerization and/or cracking is completed at a pressure of from about 10 atm to about 30 atm.

In some embodiments, the composition further comprises vegetable oil, waste oil, animal fat, or a combination thereof.

In some embodiments, the composition further comprises soybean oil, corn oil, canola oil, jatropha oil, sunflower oil, castor bean oil, palm oil, or a combination thereof.

In some embodiments, the composition further comprises distillers corn oil.

In some embodiments, the composition further comprises hydrogen.

In some embodiments, the composition comprises the substituted or unsubstituted lactone in an amount of at least 40 wt %.

In some embodiments, the composition comprises the substituted or unsubstituted lactone in an amount of at least 60 wt %.

In some embodiments, the sustainable fuel comprises sustainable aviation fuel (SAF), renewable diesel, sustainable light fuel, renewable naphtha, or a combination thereof.

In some embodiments, the sustainable fuel comprises SAF in an amount of at least 30 wt %.

In some embodiments, the sustainable fuel comprises SAF in an amount of at least 40 wt %.

In some embodiments, the sustainable fuel comprises SAF in an amount of at least 50 wt %.

In some embodiments, the sustainable fuel comprises SAF in an amount of from about 40 wt % to about 70 wt %.

In some embodiments, the sustainable fuel comprises SAF in an amount of about 58 wt %.

In some embodiments, the sustainable fuel comprises renewable diesel in an amount of at least 10 wt %.

In some embodiments, the sustainable fuel comprises renewable diesel in an amount of from about 10 wt % to about 30 wt %.

In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of at least 10 wt %.

In some embodiments, the sustainable fuel comprises renewable naphtha in an amount of from about 10 wt % to about 30 wt %.

In some embodiments, the sustainable fuel comprises light fuel in an amount of at least 10 wt %.

In some embodiments, the sustainable fuel comprises light fuel in an amount of from about 10 wt % to about 30 wt %.

In some embodiments, the sustainable fuel comprises: SAF in an amount of from about 40 wt % to about 70 wt %; renewable diesel in an amount of from about 10 wt % to about 30 wt %; renewable naphtha in an amount of from about 10 wt % to about 30 wt %; and light fuel in an amount of from about 10 wt % to about 30 wt %.

In some embodiments, the method further comprises combusting the light fuel and recovering the waste heat.

In some embodiments, the method further comprises combusting the renewable naphtha and recovering the waste heat.

In some embodiments, the method further comprises combusting the renewable diesel and recovering the waste heat.

In some embodiments, the one or more lipids is bioderived.

In some embodiments, the one or more lipids is derived from an organism.

In some embodiments, the one or more lipids is produced by an organism.

In some embodiments, the organism is Aureobasidium pullulans or a genetically modified version thereof.

In some embodiments, the organism produces at least 50 g/L titer of the one or more lipids.

In some embodiments, after production of the one or more lipids by the organism, the method further comprises collecting the one or more lipids.

In some embodiments, the collecting comprises liquid-liquid extraction, distillation, physical separation, mechanical cell disruption, supercritical fluid extraction, gravimetric separation, flash evaporation, or a combination thereof.

In some embodiments, the liquid-liquid extraction comprises use of a solvent comprising chloroform, methanol, butanol, isopropanol, hexane, toluene, petroleum ether, methyl ethyl ketone (MEK), acetonitrile, ethyl acetate, or a combination thereof.

In some embodiments, the liquid-liquid extraction comprises countercurrent liquid extraction.

In some embodiments, the liquid-liquid extraction is completed at a temperature of from about 25° C. to about 60° C.

In some embodiments, the liquid-liquid extraction is completed at a temperature of from about 35° C. to about 50° C.

In some embodiments, the distillation is water stripping distillation, steam distillation, vacuum distillation, azeotropic distillation, fractional distillation, or simple distillation.

In some embodiments, the distillation comprises water stripping distillation.

In some embodiments, the distillation comprises use of a reboiler and a condenser.

In some embodiments, the reboiler comprises a temperature of from about 80° C. to about 120° C.

In some embodiments, the reboiler comprises a temperature of from about 90° C. to about 110° C.

In some embodiments, the condenser comprises a temperature of from about 50° C. to about 90° C.

In some embodiments, the condenser comprises a temperature of from about 60° C. to about 80° C.

In some embodiments, the physical separation comprises centrifugation, decantation, or a combination thereof.

In some embodiments, the physical separation is completed at a temperature of from about 25° C. to about 60° C.

In some embodiments, the physical separation is completed at a temperature of from about 35° C. to about 50° C.

In some embodiments, the centrifugation comprises disc stack centrifugation.

In some embodiments, the collecting comprises flash evaporation.

In some embodiments, the flash evaporation comprises use of a flash drum at a temperature of from about 35° C. to about 55° C.

In some embodiments, the collecting comprises liquid-liquid extraction, distillation, physical separation, and flash evaporation.

In some embodiments, the method further comprises reacting and distilling the one or more lipids to provide one or more substituted or unsubstituted lactones.

In some embodiments, the reacting comprises contacting the at least a portion of the lipids with a catalyst.

In some embodiments, the catalyst is an acid catalyst.

In some embodiments, the acid catalyst is hydrochloric acid, sulfuric acid, hydrobromic acid, phosphoric acid, iodic acid, or a combination thereof.

In some embodiments, the method does not comprise the use of a catalyst.

In some embodiments, the distillation comprises simple distillation, fractional distillation, vacuum distillation, spinning band distillation, azeotropic distillation, wiped film distillation, or a combination thereof.

In some embodiments, the distillation comprises wiped film distillation.

In some embodiments, the reacting and distillation provides a yield of the one or more substituted or unsubstituted lactones of at least 70 wt %.

In some embodiments, the sustainable fuel comprises a carbon intensity (CI) of less than 40 g CO₂e/MJ.

In some embodiments, a cost of producing the SAF is at least 60% lower than the cost of producing aviation fuel using HEFA and oilseed oil as a feedstock.

In some embodiments, a cost of producing the SAF is at least 15% lower than the cost of producing aviation fuel using HEFA and palm oil as a feedstock.

In some embodiments, provided herein is an aviation fuel, comprising:

• • (a) C₈-C₁₆ deoxygenated hydrocarbons, comprising:
  • (i) C₈-C₁₀ deoxygenated hydrocarbons in an amount of at least 70 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons;
  • (ii) C₁₁-C₁₃ deoxygenated hydrocarbons in an amount of at most 15 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons;
  • (iii) C₁₄-C₁₆ deoxygenated hydrocarbons in an amount of at most 15 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons; and
  • (d) one or more of sulfur, nitrogen, phosphorus, potassium, magnesium, calcium, sodium, iron, aluminum, and silicon.

In some embodiments, the C₈-C₁₀ deoxygenated hydrocarbons are present in an amount of at least about 70 wt % relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₈-C₁₀ deoxygenated hydrocarbons are present in an amount of from about 70 wt % to about 100 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₈-C₁₀ deoxygenated hydrocarbons are present in an amount of about 90 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₁₁-C₁₃ deoxygenated hydrocarbons are present in an amount of less than about 15 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₁₁-C₁₃ deoxygenated hydrocarbons are present in an amount of from about 1 wt % to about 15 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₁₁-C₁₃ deoxygenated hydrocarbons are present in an amount of about 5 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₁₄-C₁₆ deoxygenated hydrocarbons are present in an amount of less than about 15 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₁₄-C₁₆ deoxygenated hydrocarbons are present in an amount of from about 0.5 wt % to about 15 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the C₁₄-C₁₆ deoxygenated hydrocarbons are present in an amount of about 6 wt %, relative to the total amount of C₈-C₁₆ deoxygenated hydrocarbons.

In some embodiments, the aviation fuel comprises sulfur in an amount of from about 10 ppm to about 50 ppm.

In some embodiments, the aviation fuel comprises nitrogen in an amount of from about 50 ppm to about 100 ppm.

In some embodiments, the aviation fuel comprises phosphorus in an amount of from about 0.01 ppm to about 2 ppm.

In some embodiments, the aviation fuel comprises potassium in an amount of from about 0.5 ppm to about 3 ppm.

In some embodiments, the aviation fuel comprises magnesium in an amount of from about 0.5 ppm to about 3 ppm.

In some embodiments, the aviation fuel comprises calcium in an amount of from about 1 ppm to about 5 ppm.

In some embodiments, the aviation fuel comprises sodium in an amount of from about 3 ppm to about 8 ppm.

In some embodiments, the aviation fuel comprises iron in an amount of from about 0.05 ppm to about 0.5 ppm.

In some embodiments, the aviation fuel comprises aluminum in an amount of from about 0.1 ppm to about 0.5 ppm.

In some embodiments, the aviation fuel comprises silicon in an amount of from about 1 ppm to about 5 ppm.

In some embodiments, the sustainable aviation fuel satisfies the Jet Fuel A and/or Jet Fuel A-1 specification.

In some embodiments, the produced sustainable aviation fuel is blended with conventional/fossil-based jet fuel and the fuel blend meets the Jet Fuel A-1 specification or the Jet Fuel A specification.

In some embodiments, provided herein is a diesel fuel, comprising:

• • (a) C₁₆-C₂₂ deoxygenated hydrocarbons, comprising:
  • (i) C₁₆-C₁₈ deoxygenated hydrocarbons in an amount of at least 40 wt % relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons;
  • (ii) C₁₉-C₂₀ deoxygenated hydrocarbons in an amount of at least 15 wt % relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons;
  • (iii) C₂₁-C₂₂ deoxygenated hydrocarbons in an amount of at least 15 wt % relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons; and
  • (e) one or more of sulfur, nitrogen, phosphorus, potassium, magnesium, calcium, sodium, iron, aluminum, and silicon.

In some embodiments, the C₁₆-C₁₈ deoxygenated hydrocarbons are present in an amount of less than 70 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₁₆-C₁₈ deoxygenated hydrocarbons are present in an amount of from about 40 wt % to about 70 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₁₆-C₂₈ deoxygenated hydrocarbons are present in an amount of about 50 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₁₉-C₂₀ deoxygenated hydrocarbons are present in an amount of less than 40 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₁₉-C₂₀ deoxygenated hydrocarbons are present in an amount of from about 15 wt % to about 40 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₁₉-C₂₀ deoxygenated hydrocarbons are present in an amount of about 25 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₂₁-C₂₂ deoxygenated hydrocarbons are present in an amount of less than 40 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₂₁-C₂₂ deoxygenated hydrocarbons are present in an amount of from about 15 wt % to about 40 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the C₂₁-C₂₂ deoxygenated hydrocarbons are present in an amount of about 25 wt %, relative to the total amount of C₁₆-C₂₂ deoxygenated hydrocarbons.

In some embodiments, the diesel fuel comprises sulfur in an amount of from about 10 ppm to about 50 ppm.

In some embodiments, the diesel fuel comprises nitrogen in an amount of from about 50 ppm to about 100 ppm.

In some embodiments, the diesel fuel comprises phosphorus in an amount of from about 0.01 ppm to about 2 ppm.

In some embodiments, the diesel fuel comprises potassium in an amount of from about 0.5 ppm to about 3 ppm.

In some embodiments, the diesel fuel comprises magnesium in an amount of from about 0.5 ppm to about 3 ppm.

In some embodiments, the diesel fuel comprises calcium in an amount of from about 1 ppm to about 5 ppm.

In some embodiments, the diesel fuel comprises sodium in an amount of from about 3 ppm to about 8 ppm.

In some embodiments, the diesel fuel comprises iron in an amount of from about 0.05 ppm to about 0.5 ppm.

In some embodiments, the diesel fuel comprises aluminum in an amount of from about 0.1 ppm to about 0.5 ppm.

In some embodiments, the diesel fuel comprises silicon in an amount of from about 1 ppm to about 5 ppm.

In some embodiments, the diesel fuel is Diesel #1, Diesel #2, or a combination thereof.

While preferred embodiments of the present disclosure have been shown and described herein, it will be obvious to those skilled in the art that such embodiments are provided by way of example only. Numerous variations, changes, and substitutions will now occur to those skilled in the art without departing from the disclosure. It should be understood that various alternatives to the embodiments of the present disclosure may be employed in practicing the present disclosure. It is intended that the following claims define the scope of the present disclosure and that methods and structures within the scope of these claims and their equivalents be covered thereby.