Methods of refining and producing dibasic esters and acids from natural oil feedstocks

Patent metadata

Field	Value
Publication number	US-9284512-B2
Application number	US-201514628467-A
Country	US
Kind code	B2
Filing date	Feb 23, 2015
Priority date	Oct 12, 2009
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

First claim

What is claimed is:

1. A method of refining a natural oil, comprising:
providing a terminal olefin ester and an internal olefin ester, wherein the terminal olefin ester is an ester of 9-decenoic acid and the internal olefin ester is an ester of 9-dodecenoic acid; and
reacting the terminal olefin ester with the internal olefin ester in the presence of a metathesis catalyst to form a dibasic ester of 9-octadecenedioic acid and 1-butene.

2. The method of claim 1 , wherein the ester of 9-decenoic acid is an alkyl ester of 9-decenoic acid.

3. The method of claim 2 , wherein the alkyl ester of 9-decenoic acid is methyl 9-decenoate.

4. The method of claim 1 , wherein the ester of 9-dodecenoic acid is an alkyl ester of 9-dodecenoic acid.

5. The method of claim 4 , wherein the alkyl ester of 9-dodecenoic acid is methyl 9-dodecenoate.

6. The method of claim 1 , wherein the dibasic ester of 9-octadecenedioic acid is a dialkyl ester of 9-octadecenedioic acid.

7. The method of claim 6 , wherein the dialkyl ester of 9-octadecenedioic acid is dimethyl 9-octadecenedioate.

8. The method of claim 1 , comprising separating at least a portion of the 1-butene from the dibasic ester of 9-octadecenedioic acid during the reacting.

9. The method of claim 1 , comprising hydrolyzing the dibasic ester of 9-octadecenedioic acid to form 9-octadecenedioic acid.

10. The method of claim 1 , wherein at least a portion of the internal olefin ester is formed by reacting a portion of the terminal olefin ester with a low-molecular-weight internal olefin.

11. The method of claim 10 , wherein the low-molecular-weight internal olefin is selected from the group consisting of: 2-pentene, 3-hexene, 3-heptene, 3-octnene, 3-nonene, and mixtures thereof.

12. The method of claim 11 , wherein the low-molecular-weight internal olefin is 3-hexene.

13. The method of claim 1 , wherein the ester of 9-decenoic acid is formed by a process that comprises reacting a first natural oil fatty acid ester with a first low-molecular weight olefin in the presence of a metathesis catalyst.

14. The method of claim 13 , wherein the first low-molecular-weight-olefin is selected from the group consisting of: ethylene, propylene, 1-butene, and mixtures thereof.

15. The method of claim 14 , wherein the first low-molecular-weight olefin is ethylene.

16. The method of claim 14 , wherein the first low-molecular-weight olefin is 1-butene.

17. The method of claim 13 , wherein the first natural oil fatty acid ester is an ester of a natural oil fatty acid selected from the group consisting of: oleic acid, linoleic acid, and linolenic acid.

18. The method of claim 1 , wherein the ester of 9-dodecenoic acid is formed by a process that comprises reacting a second natural oil fatty acid ester with a second low-molecular weight olefin in the presence of a metathesis catalyst.

19. The method of claim 18 , wherein the second low-molecular-weight olefin is 1-butene.

20. The method of claim 18 , wherein the second natural oil fatty acid ester is an ester of a natural oil fatty acid selected from the group consisting of: oleic acid, linoleic acid, and linolenic acid.

Assignees

• Elevance Renewable Sciences
• Elevance Renewable Sicences Inc

Inventors

• Snead Thomas E
• Cohen Steven A
• Gildon Demond L

Classifications

• C10G45/00 Primary

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