Highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester with reduced environmental pollutants, and method for producing same

Patent metadata

Field	Value
Publication number	US-9540306-B2
Application number	US-201314400652-A
Country	US
Kind code	B2
Filing date	May 14, 2013
Priority date	May 14, 2012
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

A highly unsaturated fatty acid or a highly unsaturated fatty acid ethyl ester that has been produced using as a feedstock oil a fat or oil that contains highly unsaturated fatty acids as constituent fatty acids and which has been reduced in the contents of environmental pollutants, wherein among the dioxins contained, polychlorinated dibenzoparadioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs) are contained in amounts of less than 0.05 pg-TEQ/g and coplanar PCBs (Co-PCBs) in amounts of less than 0.03 pg-TEQ/g. Also disclosed is a method for producing the highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester by the steps of removing free fatty acids and environmental pollutants by thin-film distillation from a feedstock oil, ethyl esterifying the resulting fat or oil, and refining the same by rectification and column chromatography.

First claim

The invention claimed is:

1. A method of producing a highly unsaturated fatty acid or a highly unsaturated fatty acid ethyl ester with reduced contents of polychlorinated dibenzoparadioxins (PCDDs), polychlorinated dibenzofurans (PCDFs) and coplanar PCB (Co-PCBs), wherein the highly unsaturated fatty acid is eicosapentaenoic acid or dihomo-γ-linoleic acid, the method comprising the steps of:
a) removing free fatty acids and environmental pollutants by thin-film distillation from a feedstock oil containing highly unsaturated fatty acids as constituent fatty acids;
b) ethyl esterifying the highly unsaturated fatty acids present as constituent of fat or oil contained in the product of step (a);
c) refining the product of step (b) by rectification and column chromatography,
wherein a concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 80 area %.

2. The method according to claim 1 , wherein amount of a brominated flame retardant in the highly unsaturated fatty acid or the highly unsaturated fatty acid ethyl ester is also reduced.

3. The method according to claim 1 , wherein the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 85 area %.

4. The method according to claim 1 , wherein the feedstock oil containing highly unsaturated fatty acids as constituent fatty acids is fish oil, krill oil, marine mammal oil or microorganism oil.

5. The method according to claim 1 , wherein the thin-film distillation is carried out at a temperature of 200-270° C.

6. The method according to claim 1 , wherein the thin-film distillation is carried out at a pressure of 5 Pa or lower.

7. The method according to claim 1 , wherein the thin-film distillation is carried out at a flow rate of 20-200 (kg/h)/m 2 .

8. The method according to claim 1 , wherein the thin-film distillation is molecular distillation or short path distillation.

9. The method according to claim 1 , wherein rectification is performed in three or more distillation columns.

10. The method according to claim 1 , wherein refining by column chromatography uses column chromatography of reverse-phase distribution type.

11. The method according to claim 1 , wherein in step (c) the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 90 area %.

12. The method according to claim 1 , wherein in step (c) the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 95 area %.

13. The method according to claim 1 , wherein in step (c) the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 80 area % and at most 97 area %.

14. The method according to claim 1 , wherein the method further comprises the step of:
d) producing the highly unsaturated fatty acid by hydrolyzing the highly unsaturated fatty acid ethyl ester of step (c).

Assignees

• Nippon Suisan Kaisha Ltd

Inventors

• Doisaki Nobushige
• Hata Kazuhiko
• Tokiwa Shinji
• Matsushima Kazunori

Classifications

• A61P3/02

  Nutrients, e.g. vitamins, minerals · CPC title

• C07C67/03 Primary

  by reacting an ester group with a hydroxy group · CPC title

• C07C51/47

  by solid-liquid treatment; by chemisorption · CPC title

• A61K31/232

  having three or more double bonds, e.g. etretinate · CPC title

• A61K31/20

  having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids · CPC title