Methods of refining and producing dibasic esters and acids from natural oil feedstocks
View Patent ↗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.
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.