Free-polyunsaturated-fatty-acid-containing composition and method for manufacturing same

Patent metadata

Field	Value
Publication number	US-11193085-B2
Application number	US-201815906645-A
Country	US
Kind code	B2
Filing date	Feb 27, 2018
Priority date	Aug 31, 2015
Publication date	Dec 7, 2021
Grant date	Dec 7, 2021

Abstract

Provided is a free-polyunsaturated-fatty-acid-containing composition that has a total metal content of 0.1 ppm or less and that comprises at least one free polyunsaturated fatty acid having 20 or more carbon atoms, in an amount that is at least 80.0% of the amount of fatty acids in the composition; and a method for manufacturing a free-polyunsaturated-fatty-acid-containing composition, comprising: providing a raw material composition containing at least one polyunsaturated fatty acid having 20 or more carbon atoms; performing a hydrolysis treatment on a reaction solution prepared by combining the provided raw material composition, a lower alcohol, water having a total metal content of 0.01 ppm or less, and an alkali catalyst; and limiting the contact between the reaction composition and the metal after the hydrolysis treatment so that the product T [cm2×days] of the contact surface area [cm2] per 1 g and the contact time [days] between the composition and the metal is 100 or less.

First claim

What is claimed is:

1. A free polyunsaturated fatty acid-containing composition, (i) comprising at least one free polyunsaturated fatty acid in an amount that a content thereof is 80.0% or greater of fatty acids in the composition; (ii) having a content of the conjugated unsaturated fatty acid in the range of 0.001% to 1.2% of the fatty acids in the composition; and (iii) having a total iron content of being 0.1 ppm or less,
wherein the polyunsaturated fatty acid is selected from the group consisting of eicosadienoic acid, dihomo-γ-linolenic acid, Mead acid, eicosatetraenoic acid, arachidonic acid, eicosapentaenoic acid, docosatetraenoic acid, docosapentaenoic acid, and docosahexaenoic acid.

2. The free polyunsaturated fatty acid-containing composition according to claim 1 , wherein a peroxide value is 5.0 meq/kg or less.

3. The free polyunsaturated fatty acid-containing composition according to claim 1 , wherein an anisidine value is 5.0 or less.

4. The free polyunsaturated fatty acid-containing composition according to claim 1 , wherein, in a case where a membrane evaluation test described below is performed by using the free polyunsaturated fatty acid-containing composition, a time passed until a membrane formed by using a test solution prepared from the free polyunsaturated fatty acid-containing composition is broken is 1.4 or greater when a time passed until a membrane formed by using a reference solution is broken is expressed as 1;
Membrane evaluation test:
a circular frame for the membrane evaluation test, the circular frame having a plurality of inner frames, is immersed in a fatty acid test solution (a reference solution or a test solution) in a condition at a temperature of 25° C., 1 atmosphere, and a relative humidity of 55%, then membranes are formed in sections formed by the plurality of inner frames by bringing the circular frame above a liquid surface, and a time required for at least one formed membrane to be broken is measured;
Preparation of test solution:
Reference solution:
an aqueous solution of iron (II) sulfate heptahydrate is added to the free polyunsaturated fatty acid composition such that an iron concentration is 100 ppm, ethanol is added and homogenized, and then a solvent is removed by using vacuum to prepare a free polyunsaturated fatty acid composition containing 100 ppm of iron in the composition; and 0.5 g of the free polyunsaturated fatty acid-containing composition containing 100 ppm of iron, 0.15 g of 48 wt. % sodium hydroxide, and 9.35 g of purified water are mixed to prepare an aqueous solution containing approximately 5 wt. % of free polyunsaturated fatty acid sodium in the aqueous solution, and the obtained aqueous solution is used as a reference solution;
Test solution:
an aqueous solution containing approximately 5 wt. % of free polyunsaturated fatty acid sodium in the aqueous solution is prepared by mixing 0.5 g of the free polyunsaturated fatty acid-containing composition, 0.15 g of 48 wt. % sodium hydroxide, and 9.35 g of purified water, and the obtained aqueous solution is used as a test solution; and
Preparation of circular frame for test:
a tool that is formed from plastic and that has five sections divided by inner frames having a thickness of 2 mm in an outer frame having a diameter of 64 mm, an inner diameter of 52 mm, and a thickness of 3 mm is used as the circular frame for test.

5. The free polyunsaturated fatty acid-containing composition of claim 1 , wherein a content of the fatty acid alkyl ester is 0.2% or less of the fatty acids in the composition.

Assignees

• Nippon Suisan Kaisha Ltd

Inventors

• Yamaguchi Hideaki
• Doisaki Nobushige
• Sato Seizo
• Kosuge Yuhei

Classifications

• C11C3/003

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

• C11C1/04 Primary

  by hydrolysis · CPC title

• C07C51/09

  from carboxylic acid esters or lactones · CPC title

• A23L33/12

  Fatty acids or derivatives thereof · CPC title

• A23K20/158

  Fatty acids; Fats; Products containing oils or fats · CPC title