IP Library Granted Patent US 7,138,256
Granted Patent B2
US 7,138,256 · App. 10/516,987 · Granted Nov 21, 2006

Processes for preparing conjugated linoleic acid from conjugated linoleic acid esters

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Quick Facts
Patent No.
US 7,138,256
App. No.
10/516,987
Granted
Nov 21, 2006
Kind
B2
Abstract

Processes for preparing conjugated linoleic acid are described wherein a conjugated linoleic acid lower alkyl ester is subjected to hydrolysis in the presence of an enzyme to form a hydrolyzate comprising a conjugated linoleic acid and a lower alkanol, wherein at least a portion of the lower alkanol is continuously removed; the hydrolyzate is separated into an organic phase and an aqueous/alcoholic phase; and the conjugated linoleic acid is separated from the organic phase.

Claims (22)

1. A process comprising:

(a) subjecting a conjugated linoleic acid lower alkyl ester to hydrolysis in the presence of an enzyme to form a hydrolyzate comprising a conjugated linoleic acid and a lower alkanol, wherein at least a portion of the lower alkanol is continuously removed;

(b) separating the hydrolyzate into an organic phase and an aqueous/alcoholic phase; and

(c) separating the conjugated linoleic acid from the organic phase.

2. The process according to claim 1 , wherein the conjugated linoleic acid corresponds to the general formula (I):

R 1 CO—OR 2   (I)

wherein R 1 CO represents a linoleic acid acyl group having conjugated double bonds and R 2 represents an alkyl group having from 1 to 4 carbons.

3. The process according to claim 1 , wherein the enzyme comprises a compound selected from the group consisting of esterases, lipases and mixtures thereof.

4. The process according to claim 1 , wherein the enzyme comprises at least one microorganism selected from the group consisting of Alcaligenes., Aspergillus niger, Candida antarctica A, Candida antarctica B, Candida cylindracea, Chromobacterium viscosum, Rhizomucor miehei, Penicilium camemberti, Penicilium roqueforti, Porcine pancreas, Pseudomonas cepacia, Pseudomonas fluorescens, Rhizopus javanicus, Rhizopus oryzae , and Thermoinyces lanugenosus.

5. The process according to claim 2 , wherein the enzyme comprises at least one microorganism selected from the group consisting of Alcaligenes., Aspergillus niger, Candida antarctica A, Candida antarctica B, Candida cylindracea, Chromobacterium viscosum, Rhizomucor miehei, Penicilium camemberti, Penicilium roqueforti, Porcine pancreas, Pseudomonas cepacia, Pseudomonas flucrescens, Rhizopus javanicus, Rhizopus oryzae , and Thermomyces lanugenosus.

6. The process according to claim 1 , wherein the enzyme comprises at least one microorganism selected from the group consisting of Candida antarctica B, Chromobacterium viscosum , and Thermomyces lanugenosus.

7. The process according to claim 2 , wherein the enzyme comprises at least one microorganism selected from the group consisting of Candida antarctica B, Chromobacterium viscosum , and Thermomyces lanugenosus.

8. The process according to claim 1 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C.

9. The process according to claim 2 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C.

10. The process according to claim 6 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C.

11. The process according to claim 7 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C.

12. The process according to claim 1 , wherein the hydrolysis is carried out to a conversion of 60% by weight.

13. The process according to claim 1 , wherein a constant water content of from 30 to 70% by weight is maintained during the hydrolysis and at least a portion of the water/lower alkanol phase is continuously removed by application of a vacuum of from 20 to 60±5 mbar.

14. The process according to claim 1 , wherein water content is adjusted to from 0 to 20% by weight during the hydrolysis and at least a portion of the water/lower alkanol phase is continuously removed by application of a vacuum of from 20 to 60±5 mbar.

15. The process according to claim 1 , wherein the hydrolysis is carried out in two or more stages and a water content of from 50 to 75% by weight is used in each stage.

16. The process according to claim 1 , wherein the hydrolysis is carried out to a conversion of greater than 90% by weight.

17. The process according to claim 1 , wherein the hydrolysis is carried out to a conversion of greater than 99% by weight.

Assignments (2)
PATENT AND TRADEMARK TRANSFER AND LICENSE AGREEMENT Recorded Nov 11, 2008
From: COGNIS DEUTSCHLAND GMBH & CO. KG
To: COGNIS IP MANAGEMENT GMBH
Reel/Frame 021805/0578 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2004
From: ZANDER, LARS; BUSCH, STEFAN; MEYER, CAROLIN; BOTH, SABINE; SCHOERKEN, ULRICH
To: COGNIS DEUTSCHLAND GMBH & CO. KG
Reel/Frame 016727/0147 →