RENEWABLE CHEMICAL PRODUCTION FROM NOVEL FATTY ACID FEEDSTOCKS

• US 20110165634A1
• Filed: 12/29/2010
• Published: 07/07/2011
• Est. Priority Date: 11/28/2008
• Status: Active Grant

• Current Assignee: Corbion Biotech, Inc. (Corbion NV)
• Original Assignee: Solazyme Inc.
• Inventors: Rudenko, George, Somanchi, Aravind, Chua, Penelope, Espina, Karen, Franklin, Scott
• Granted Patent: US 8,222,010 B2
• Time in Patent Office: Days
• US Class Current: 435/123
• CPC Class Codes: C07C 1/2078 by a transformation in which at least one -C(=O)-O- moiety is eliminated
• CPC Class Codes: C07K 2319/01 containing a localisation/targetting motif
• CPC Class Codes: C10L 1/02 essentially based on components consisting of carbon, hydrogen, and oxygen only
• CPC Class Codes: C12N 15/79 Vectors or expression systems specially adapted for eukaryotic hosts
• CPC Class Codes: C12N 9/00 Enzymes; Proenzymes; Compositions thereof preparations containing enzymes for cleaning teeth A61K8/66, A61Q11/00; medicinal preparations containing enzymes or proenzymes A61K38/43; enzyme containing detergent compositions C11D; enzymes with nucleic acid structure, e.g. ribozymes, C12N15/113; Processes for preparing, activating, inhibiting, separating or purifying enzymes preparation of malt C12C1/00
• CPC Class Codes: C12N 9/16 acting on ester bonds (3.1)
• CPC Class Codes: C12N 9/2402 hydrolysing O- and S- glycosyl compounds (3.2.1)
• CPC Class Codes: C12P 7/20 Glycerol
• CPC Class Codes: C12P 7/64 Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
• CPC Class Codes: C12P 7/6409 Fatty acids
• CPC Class Codes: C12P 7/6418 by hydrolysis of fatty acid esters
• CPC Class Codes: C12P 7/6427 Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
• CPC Class Codes: C12P 7/6458 by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
• CPC Class Codes: C12P 7/6463 obtained from glyceride producing microorganisms, e.g. single cell oil
• CPC Class Codes: C12P 7/649 Biodiesel, i.e. fatty acid alkyl esters
• CPC Class Codes: C12Y 301/02014 Oleoyl-[acyl-carrier-protein] hydrolase (3.1.2.14), i.e. ACP-thioesterase
• CPC Class Codes: C12Y 302/01026 Beta-fructofuranosidase (3.2.1.26), i.e. invertase
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts
• CPC Class Codes: Y02P 60/87 Re-use of by-products of food processing for fodder production
• CPC Class Codes: Y02T 50/678 : Aviation using fuels of non-fossil origin

Abstract

Disclosed herein are methods of manufacturing renewable chemicals through the manufacture of novel triglyceride oils followed by chemical modification of the oils. Methods such as transesterification, hydrogenation, hydrocracking, deoxygenation, isomerization, interesterification, hydroxylation, hydrolysis and saponification are disclosed. Novel oils containing fatty acid chain lengths of C8, C10, C12 or C14 are also disclosed and are useful as feedstocks in the methods of the invention.

Claims

1. A method of manufacturing a chemical, comprising the steps of:

A. cultivating a cell of the genus Prototheca that comprises an exogenous fatty acyl-ACP thioesterase gene that encodes a fatty acyl-ACP thioesterase having hydrolysis activity towards one or more fatty acyl-ACP substrates of chain length C8, C10, C12, or C14, wherein the cell produces triglyceride oil that has

a. a lipid profile of at least 4% C₈-C₁₄; and

b. at least one of the following attributes;

i. less than 0.4 micrograms/ml of total carotenoids;

ii. less than 0.001 micrograms/ml of lycopene;

iii. less than 0.02 micrograms/ml of beta carotene;

iv. less than 0.02 milligrams of chlorophyll per kilogram of oil;

v. 0.40-0.60 milligrams of gamma tocopherol per 100 grams of oil;

vi. 3-9 mg campesterol per 100 grams of oil;

vii. less than 0.5 milligrams of total tocotrienols per gram of oil; and

B. performing one or more chemical reactions comprising transesterification, hydrogenation, hydrocracking, deoxygenation, isomerization, interesterification, hydroxylation, and/or hydrolysis on a triglyceride oil, whereby the chemical is produced.

2. The method of claim 1 wherein the one or more chemical reactions further comprise performing an amination reaction to produce fatty nitrogen compounds.

3. The method of claim 1 wherein the one or more chemical reactions further comprise performing a hydroxylation reaction to produce hydroxylated fatty acids.

4. The method of claim 1 wherein the one or more chemical reactions further comprise performing an epoxidation reaction to produce epoxidized triglyceride oils.

5. The method of claim 1, wherein the one or more chemical reactions comprise interesterification and the chemical produced is an edible fat for food products.

6. The method of claim 5, wherein the interesterification is a directed interesterification.

7. The method of claim 1, wherein the one or more chemical reactions comprise transesterification followed by deoxygenation and the chemical produced is a fatty alcohol.

8. The method of claim 1, wherein the fatty acyl-ACP thioesterase amino acid sequence is identical to a fatty acyl-ACP thioesterase in Table 3.

9. The method of claim 1, wherein the fatty acyl-ACP thioesterase gene is from at least one of the following species Umbellularia califormica, Cinnamomum camphora, Cuphea hookeriana, Cuphea palustris, and Ulmus americana.

10. The method of claim 1, wherein the triglyceride oil has a lipid profile of at least 30% C8-14.

11. A method of manufacturing a chemical, comprising the steps of:

A. cultivating a cell that comprises an exogenous fatty acyl-ACP thioesterase gene that encodes a fatty acyl-ACP thioesterase having hydrolysis activity towards one or more fatty acyl-ACP substrates of chain length C8, C10, C12, or C14, wherein the cell is an obligate heterotroph and produces triglyceride oil that has

a. a lipid profile of at least 4% C₈-C₁₄; and

b. at least one of the following attributes;

i. less than 0.4 micrograms/ml of total carotenoids;

ii. less than 0.001 micrograms/ml of lycopene;

iii. less than 0.02 micrograms/ml of beta carotene;

iv. less than 0.02 milligrams of chlorophyll per kilogram of oil;

v. 0.40-0.60 milligrams of gamma tocopherol per 100 grams of oil;

vi. 3-9 mg campesterol per 100 grams of oil;

vii. less than 0.5 milligrams of total tocotrienols per gram of oil; and

B. performing one or more chemical reactions comprising transesterification, hydrogenation, hydrocracking, deoxygenation, isomerization, interesterification, hydroxylation, and/or hydrolysis on a triglyceride oil, whereby the chemical is produced.

12. The method of claim 11, wherein the one or more chemical reactions comprise performing a hydrolysis reaction.

13. The method of claim 11, wherein the triglyceride oil is blended with at least one of the following oils before performing the one or more chemical reactions:

soy, rapeseed, canola, palm, palm kernel, coconut, corn, waste vegetable, Chinese tallow, olive, sunflower, cotton seed, chicken fat, beef tallow, porcine tallow, microalgae, macroalgae, Cuphea, flax, peanut, choice white grease, lard, Camelina sativa, mustard seed, cashew nut, oats, lupine kenaf, calendula, hemp, coffee, hazelnut, euphorbia, pumpkin seed, coriander, camellia, sesame, safflower, rice, tung tree, cocoa, copra, plum poppy, castor beans, pecan, jojoba, macademia, Brazil nuts, avocado, petroleum, or a distillate fraction of any of the proceeding oils.

14. The method of claim 11, wherein the one or more chemical reactions comprise hydrogenation and deoxygenation and the chemical produced is separated from naphtha components.

15. The method of claim 11, wherein the one or more chemical reactions comprise transesterification and the chemical produced is a fatty acid ester.

16. The method of claim 11, wherein the cultivation of the cell is cultured in a medium containing sucrose.

17. The method of claim 16, wherein the cell further comprises an exogenous sucrose invertase gene.

18. The method of claim 11, wherein the cell further comprises an endogenous desaturase gene that is knocked out or down-regulated.

19. The method of claim 11, wherein the one or more chemical reactions comprise interesterification and the chemical product is an edible fat for food products.

20. The method of claim 11, wherein the triglyceride oil has a lipid profile of at least 30% C₈-C₁₄.