Composition containing highly unsaturated fatty acid or alkyl ester thereof and a method for producing the same

Patent metadata

Field	Value
Publication number	US-10696924-B1
Application number	US-201916404662-A
Country	US
Kind code	B1
Filing date	May 6, 2019
Priority date	Dec 12, 2018
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

MEANS FOR SOLVING A composition that contains fatty acids or fatty acid alkyl esters as its major component, the composition containing highly unsaturated fatty acid or alkyl ester thereof, wherein the proportion of the highly unsaturated fatty acid in the constituent fatty acids of the composition is 50 area % or more and wherein the concentration of 3-MCPD as found upon analyzing the composition by American Oil Chemists' Society official method Cd 29b-13 assay A is less than 1.80 ppm.

First claim

What is claimed is:

1. A composition that contains fatty acids or fatty acid alkyl esters as its major component, the composition containing highly unsaturated fatty acid or alkyl ester thereof, wherein the proportion of the highly unsaturated fatty acid in the constituent fatty acids of the composition is 50 area % or more and wherein the concentration of 3-MCPD as found upon analyzing the composition by American Oil Chemists' Society official method Cd 29b-13 assay A is less than 1.80 ppm, and the concentration of trans-isomers in the composition is 0.01 area % or more.

2. The composition according to claim 1 , wherein the proportion of the highly unsaturated fatty acid in the constituent fatty acids of the composition is 70 area % or more.

3. The composition according to claim 1 , wherein the concentration of 3-MCPD as found upon analyzing the composition by American Oil Chemists' Society official method Cd 29b-13 assay A is less than a detection limit.

4. The composition according to claim 1 , wherein the highly unsaturated fatty acid is eicosapentaenoic acid, docosahexaenoic acid, dihomo-γ-linolenic acid, arachidonic acid, or a combination thereof.

5. The composition according to claim 1 , which is a distillation product.

6. The composition according to claim 1 , wherein a raw material of the composition is a fish oil, a microorganism oil, a vegetable oil or a marine animal oil.

7. A distillation feed composition containing a highly unsaturated fatty acid alkyl ester,
wherein the highly unsaturated fatty acid alkyl ester comprises a highly unsaturated fatty acid alkyl ester to be enriched and
wherein the concentration of monoacyl glycerol comprising as constituent fatty acid a fatty acid having 5 or more carbon atoms fewer than the highly unsaturated fatty acid which constitutes the highly unsaturated fatty acid alkyl ester to be enriched is greater than zero ppm and less than 10,000 ppm and/or the iron concentration is less than 0.20 ppm.

8. The composition according to claim 7 , wherein the concentration of monoacyl glycerol comprising as the constituent fatty acid a fatty acid having 6 carbon atoms fewer than the highly unsaturated fatty acid which constitutes the highly unsaturated fatty acid alkyl ester to be enriched is less than 10,000 ppm.

9. The composition according to claim 7 , wherein the chlorine concentration is less than 10 ppm.

10. The composition according to claim 7 , wherein the highly unsaturated fatty acid alkyl ester to be enriched is an alkyl ester of eicosapentaenoic acid, docosahexaenoic acid, dihomo-γ-linolenic acid, or arachidonic acid, or a combination thereof.

11. The composition according to claim 7 , wherein a raw material of the composition is a fish oil, a microorganism oil, a vegetable oil or a marine animal oil.

12. A method for producing a composition containing a highly unsaturated fatty acid or an alkyl ester thereof, which comprises:
(1) alkyl esterifying a raw material containing a triglyceride comprising a highly unsaturated fatty acid as constituent fatty acid to prepare a composition containing a highly unsaturated fatty acid alkyl ester;
(2) at least one selected from among
(a) reducing a monoacyl glycerol concentration in the composition prepared in step (1) to less than 10,000 ppm, where the monoacyl glycerol comprises as constituent fatty acid a fatty acid that has 5 or more carbon atoms fewer than the highly unsaturated fatty acid that constitutes the highly unsaturated fatty acid alkyl ester to be enriched in the composition prepared in step (1),
(b) reducing an iron concentration in the composition prepared in step (1) to less than 0.20 ppm, and
(c) reducing a chlorine concentration in the composition prepared in step (1) to less than 10 ppm; and

(3) distilling the composition resulting from step (2) and collecting the main distillate fraction.

13. The method according to claim 12 , wherein the concentration of 3-MCPD as found upon analyzing the main distillate fraction from step (3) by American Oil Chemists' Society official method Cd 29b-13 assay A is less than 1.80 ppm.

14. The method according to claim 12 , wherein step (2)(a) is performed by silica gel chromatography.

15. The method according to claim 12 , wherein distillation in step (3) is rectification.

16. The method according to claim 12 , wherein the concentration of monoacyl glycerol comprising as the constituent fatty acid a fatty acid that has 6 carbon atoms fewer than the highly unsaturated fatty acid that constitutes the highly unsaturated fatty acid alkyl ester to be enriched is reduced to less than 10,000 ppm in step (2).

17. The method according to claim 12 , wherein the highly unsaturated fatty acid is eicosapentaenoic acid, docosahexaenoic acid, dihomo-γ-linolenic acid, arachidonic acid, or a combination thereof.

18. The method according to claim 12 , wherein the raw material is a fish oil, a microorganism oil, a vegetable oil or a marine animal oil.

Assignees

• Nippon Suisan Kaisha Ltd

Inventors

• Doisaki Nobushige
• Furihata Kiyomi
• Yamaguchi Hideaki

Classifications

• C11C3/10 Primary

  Ester interchange · CPC title

• C11C3/003

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title

• C11B3/12 Primary

  by distillation · CPC title

• C11B3/00 Primary

  Refining fats or fatty oils · CPC title

• A23D9/02

  characterised by the production or working-up · CPC title