Lauric ester compositions

• US 9,394,550 B2
• Filed: 03/27/2015
• Issued: 07/19/2016
• Est. Priority Date: 03/28/2014
• Status: Active Grant

• Current Assignee: Corbion Biotech, Inc. (Corbion NV)
• Original Assignee: Terravia Holdings, Inc. (Corbion NV)
• Inventors: Dummer, Timothy, Bond, Risha
• Primary Examiner(s): Cutliff, Yate K
• Application Number:
  US14/671,894
• Publication Number:
  US 20150275149A1
• Time in Patent Office: 480 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C09D 9/005 containing organic solvents
• CPC Class Codes: C09K 3/00 Materials not provided for elsewhere
• CPC Class Codes: C09K 8/52 Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/08 with fatty acids
• CPC Class Codes: C11D 3/188 Terpenes
• CPC Class Codes: C11D 3/2093 Esters; Carbonates
• CPC Class Codes: C11D 7/248 Terpenes
• CPC Class Codes: C11D 7/266 Esters or carbonates
• CPC Class Codes: C12P 7/6436 Fatty acid esters

Abstract

Provided are compositions containing alkyl esters derived from triglyceride oils produced from genetically engineered microalgae. Specific embodiments relate to esters derived from oils with high C10-C12 fatty acid profile. Compositions comprising the esters include cleaning products, completion fluids, work-over fluids, drilling fluids, metal working fluids, lubricants, paints, and inks.

Claims

1. A composition comprising C1-C4 esters of fatty acids derived from triglyceride oil produced by a microalga that is a recombinant oleaginous cell of the genus Prototheca, the oil having an altered fatty acid profile relative to an oil produced by a non-recombinant microalga of the genus Prototheca, the altered fatty acid profile having at least 10% C10:

0 and 40% C12;

0 fatty acids, the composition having a reduced odor compared to a composition where all the fatty acids are derived from vegetable or animal triglyceride oil having a fatty acid profile of at least 40% C12;

0 fatty acids.

2. The composition of claim 1, wherein the odor is an unpleasant odor characteristic of a C6 or C8 fatty acid or ester thereof.

3. The composition of claim 1, wherein the ester is a methyl, ethyl, propyl, iso-propyl, butyl, or a tert-butyl ester.

4. The composition of claim 1, having an altered fatty acid profile wherein C12:

0>

C10;

0>

C14;

0.

5. The composition of claim 1, wherein at least 50% of the fatty acids are C12:

0 fatty acids or the combined total amount of C;

10 and C;

12 fatty acids is at least 60%.

6. The composition of claim 1, wherein at least 15% of the fatty acids are C10:

0 fatty acids.

7. The composition of claim 1, wherein 15-25% of the fatty acids are C10:

0 fatty acids.

8. The composition of claim 1, wherein 10-15% of the fatty acids are C14:

0 fatty acids.

9. The composition of claim 1, wherein less than 8%, 7%, or 6% of the fatty acids are C16:

0 fatty acids.

10. The composition of claim 1, wherein less than 0.5% of the fatty acids are C8:

0 fatty acids.

11. The composition of claim 1, wherein less than 0.1%, 0.01%, or 0.001% of the fatty acids are C6:

0 fatty acids.

12. The composition of claim 1, comprising a terpene.

13. The composition of claim 12, wherein the terpene is limonene.

14. A method for preparing a composition comprising C1-C4 esters of fatty acids derived from triglyceride oil produced by a microalga of the genus Prototheca, the composition having a reduced odor compared to a composition where all the fatty acids are derived from vegetable oil, the method comprising:

a) providing oil produced by a microalga that is a recombinant oleaginous cell of the genus Prototheca, the oil comprising triacylglycerides having an altered fatty acid profile relative to an oil produced by a non-recombinant microalga of the genus Prototheca, wherein the most abundant fatty acids are C12;

0 fatty acids; and

b) treating the triacylglycerides with a C1-C4 alcohol under transesterification conditions to form C1-C4 esters of the microalgal derived fatty acids.

15. The method of claim 14, wherein the C1-C4 alcohol is methanol, ethanol, propanol, iso-propanol, butanol, or a tert-butanol.

16. The method of claim 14 further comprising blending the C1-C4 esters of fatty acids with one or more of a terpene, a C1-C4 ester of lactic acid, a surfactant, an emulsifier, or water.