IP Library Granted Patent US 7,084,286
Granted Patent B2
US 7,084,286 · App. 10/489,017 · Granted Aug 1, 2006

Method for producing conjugated fatty acid esters

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Quick Facts
Patent No.
US 7,084,286
App. No.
10/489,017
Granted
Aug 1, 2006
Kind
B2
Abstract

Processes for preparing conjugated fatty acid products are described wherein (a) a composition which comprises a fatty acid ester having at least two unconjugated, carbon-carbon double bonds is provided; (b) the fatty acid ester is conjugated in the presence of a water-free base; (c) phosphoric acid is added to the conjugated fatty acid ester such that phosphate salts are precipitated; and (d) the precipitated phosphate salts are removed.

Claims (33)

1. A process for preparing conjugated fatty acid products, said process comprising:

(a) providing a composition which comprises a fatty acid ester having at least two unconjugated, carbon-carbon double bonds;

(b) conjugating the fatty acid ester in the presence of a water-free base;

(c) adding phosphoric acid to the conjugated fatty acid ester such that phosphate salts are precipitated; and

(d) removing the precipitated phosphate salts.

2. The process according to claim 1 , wherein the fatty acid ester comprises a fatty acid portion having from 12 to 22 carbon atoms and a fatty alcohol portion having from 1 to 5 carbon atoms.

3. The process according to claim 1 , wherein the fatty acid ester comprises a fatty acid portion having from 16 to 18 carbon atoms and a fatty alcohol portion having from 1 to 5 carbon atoms.

4. The process according to claim 1 , wherein the fatty acid ester comprises a linoleic acid alkyl ester.

5. The process according to claim 4 , wherein the linoleic acid alkyl ester is selected from the group consisting of linoleic acid methyl ester, linoleic acid ethyl ester and mixtures thereof.

6. The process according to claim 1 , wherein the fatty acid ester comprises linoleic acid methyl ester.

7. The process according to claim 1 , wherein the water-free base comprises an alkali metal alcoholate.

8. The process according to claim 2 , wherein the water-free base comprises an alkali metal alcoholate.

9. The process according to claim 4 , wherein the water-free base comprises an alkali metal alcoholate.

10. The process according to claim 1 , wherein the water-free base comprises an alkali metal alcoholate having from 1 to 10 carbon atoms.

11. The process according to claim 7 , wherein the alkali metal alcoholate comprises a component selected from the group consisting of methanolates, ethanolates, t-butanolates, and mixtures thereof.

12. The process according to claim 7 , wherein the alkali metal alcoholate comprises a potassium alcoholate.

13. The process according to claim 7 , wherein the alkali metal alcoholate comprises a component selected from the group consisting of potassium methanolate, potassium ethanolate, potassium t-butanolate, and mixtures thereof.

14. The process according to claim 1 , wherein the phosphoric acid is added as an aqueous solution having a concentration of 85% or more.

15. The process according to claim 1 , further comprising adding glycerol to the conjugated fatty acid ester whereby a conjugated fatty acid glyceride is obtained via transesterification and the phosphoric acid is added to the conjugated fatty acid glyceride.

16. The process according to claim 15 , further comprising removing alcohol produced during the transesterification.

17. The process according to claim 1 , wherein the composition comprises a sunflower oil alkyl ester.

18. The process according to claim 1 , wherein the composition comprises a sunflower oil methyl ester.

19. A process for preparing conjugated fatty acid products, said process comprising:

(a) providing a composition which comprises a linoleic acid alkyl ester having at least two unconjugated, carbon-carbon double bonds;

(b) conjugating the fatty acid ester in the presence of an alkali metal alcoholate;

(c) adding an aqueous solution of phosphoric acid having a concentration of 85% or more to the conjugated fatty acid ester such that phosphate salts are precipitated; and

(d) removing the precipitated phosphate salts.

20. A process for preparing conjugated fatty acid products, said process comprising:

(a) providing a composition which comprises a linoleic acid alkyl ester having at least two unconjugated, carbon-carbon double bonds;

(b) conjugating the fatty acid ester in the presence of an alkali metal alcoholate;

(c) adding glycerol to the conjugated fatty acid ester whereby a conjugated fatty acid glyceride is obtained via transesterification and removing alcohol produced during the transesterification;

(d) adding phosphoric acid to the conjugated fatty acid glyceride such that phosphate salts are precipitated; and

(e) removing the precipitated phosphate salts.