Renewable chemical production from novel fatty acid feedstocks

• US 8,222,010 B2
• Filed: 12/29/2010
• Issued: 07/17/2012
• Est. Priority Date: 11/28/2008
• Status: Active Grant

• Current Assignee: Corbion Biotech, Inc. (Corbion NV)
• Original Assignee: Solazyme Inc.
• Inventors: Franklin, Scott, Somanchi, Aravind, Espina, Karen, Rudenko, George, Chua, Penelope
• Primary Examiner(s): Kosson, Rosanne
• Application Number:
  US12/981,409
• Publication Number:
  US 20110165634A1
• Time in Patent Office: 566 Days
• Field of Search: 435/134, 435/196, 435/233, 435/193, 435/189, 435/69.1
• US Class Current: 435/134
• 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, the method comprising:

(a) cultivating a cell of an oleaginous microorganism 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 and an exogenous invertase gene, wherein the cell is cultured in a medium comprising sucrose and the cell produces triglyceride oil that has a lipid profile of at least 4% C8-C14;

(b) performing one or more chemical reactions on the triglyceride oil to produce the chemical; and

(c) separating the chemical from the reaction mixture after performing step (b).

3. The method of claim 1, wherein the fatty acyl-ACP thioesterase gene is from Umbellularia californica, Cinnamomum camphora, Cuphea hookeriana, Cuphea palustris, or Ulmus americana.

4. The method of claim 1, wherein the oleaginous microorganism is an obligate heterotroph.

5. The method of claim 4, 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 bean, pecan, jojoba, macademia, Brazil nut, avocado, petroleum, or a distillate fraction of any of the proceeding oils.

7. The method of claim 1, wherein the one or more chemical reactions comprise a transesterification, hydrogenation, hydrocracking, hydroprocessing, hydrotreating, fluid catalytic cracking, hydrodeoxygenation, hydrodesulfurization, epoxidation, deoxygenation, isomerization, interestification, directed interestification, hydroxylation and/or hydrolysis.

8. The method of claim 1, wherein the oleaginous microorganism is a microalga.

9. The method of claim 8, wherein the microalga is of the genus Prototheca.

10. The method of claim 1, wherein the chemical comprises a fatty acid, a fatty acid methyl ester, a fatty nitrile, an ester, a dimer acid, a quat, a surfactant, a fatty alkanolamide, a fatty alcohol sulfate, a resin, an emulsifier, a fatty alcohol, an olefin, a higher alkane, a linear alkylbenzyl sulfonate, or a sulfated fatty acid.

19. The method of claim 8, wherein the microalga is of the species Prototheca moriformis.

2. A method of manufacturing a chemical, the method comprising:

(a) cultivating a cell of an oleaginous microorganism that comprises an exogenous fatty acyl-ACP thioesterase gene that encodes a fatty acyl-ACP thioesterase having hydrolysis activity toward one or more fatty acyl-ACP substrates of chain length C8, C10, C12, or C14, wherein the cell produces triglyceride oil that has a lipid profile of at least 4% C8-C14;

(b) performing one or more chemical reactions on the triglyceride oil, wherein the one or more chemical reactions comprise an amination reaction to produce the chemical, which comprises a fatty nitrogen compound; and

(c) separating the chemical from the reaction mixture after performing step (b).

11. The method of claim 2, wherein the oleaginous microorganism is an obligate heterotroph.

12. The method of claim 2, wherein the oleaginous microorganism is a microalga.

13. The method of claim 12, wherein the microalga is an obligate heterotroph.

14. The method of claim 12, wherein the microalga is of the genus Prototheca or Chlorella.

6. A method of manufacturing a chemical, the method comprising:

(a) cultivating a cell of an oleaginous microorganism 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 lipid profile of at least 4% C8-C14, wherein the cell further comprises an endogenous desaturase gene that is knocked out or down-regulated;

(b) performing one or more chemical reactions on the triglyceride oil to produce the chemical; and

(c) separating the chemical from the reaction mixture after performing step (b).

15. The method of claim 6, wherein the oleaginous microorganism is an obligate heterotroph.

16. The method of claim 6, wherein the oleaginous microorganism is a microalga.

17. The method of claim 16, wherein the microalga is an obligate heterotroph.

18. The method of claim 16, wherein the microalga is of the genus Prototheca or Chlorella.