US 10,240,172 B2Granted

Method for producing high purity omega-3 fatty acid ethyl ester

AssigneeBizen Chemical Co., Ltd.

InventorsYoshio Shimizu, Keisuke Uryu, Tetsuro Taira, Jun Fujii

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Abstract

The present invention relates to the field of methods for purifying fatty acid ethyl esters. According to the present invention, a method for obtaining a ω3 fatty acid ethyl ester, such as EPA and DHA, each as a high purity product at a high yield is provided. In the method according to the present invention, a raw material fat including EPA and DHA is treated with a lipolytic enzyme and ethyl-esterification is performed as needed; the treated substance is fractionated into a glyceride fraction and a free fatty acid fraction; a fraction comprising more EPA ester and a fraction comprising DHA ester are obtained from the respective fractions; the fraction comprising more EPA ester is purified to prepare a high-purity EPA ester; and the fraction comprising more DHA ester is purified to prepare a high-purity DHA ester.

Claims17

Dependent claims

A method for preparing an eicosapentaenoic acid ethyl ester and a docosahexaenoic acid ethyl ester from a raw material fat comprising eicosapentaenoic acid and docosahexaenoic acid, the method comprising the steps of:

(a) treating the raw material fat with a lipolytic enzyme to obtain a treated substance;
(b) fractionating the treated substance of step (a) into a glyceride fraction and a free fatty acid fraction;
(c) ethyl-esterifying each of the glyceride fraction and the free fatty acid fraction obtained in step (b) as needed to obtain an ethyl-esterified glyceride fraction and an ethyl-esterified free fatty acid fraction;
(d) purifying and fractionating the ethyl-esterified glyceride fraction into:
(1) a first fraction of the ethyl-esterified glyceride fraction comprising more docosahexaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying and comprising less eicosapentaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying;
and
(2) a second fraction of the ethyl-esterified glyceride fraction comprising more eicosapentaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying and comprising less docosahexaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying;
(e) purifying and fractionating the ethyl-esterified free fatty acid fraction into:
(3) a first fraction of the ethyl-esterified free fatty acid fraction comprising more docosahexaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying and comprising less eicosapentaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying;
and
(4) a second fraction of the ethyl-esterified free fatty acid fraction comprising more eicosapentaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying and comprising less docosahexaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying;
(f) mixing the fraction (1) of step (d) with the fraction (3) of step (e) to obtain a first mixture;
(g) mixing the fraction (2) of step (d) with the fraction (4) of step (e) to obtain a second mixture;
(h) further purifying the first mixture of step (f) to obtain a purified substance comprising a docosahexaenoic acid ethyl ester;
and
(i) further purifying the second mixture of step (g) to obtain a purified substance comprising an eicosapentaenoic acid ethyl ester.

13 more elements

(a) treating the raw material fat with a lipolytic enzyme to obtain a treated substance, which takes place under conditions for ethyl-esterifying fatty acids;
(b) fractionating the treated substance of step (a) into a glyceride fraction and an ethyl-esterified free fatty acid fraction;
(c) ethyl-esterifying the glyceride fraction obtained in step (b), to obtain an ethyl-esterified glyceride fraction;
(d) purifying and fractionating the ethyl-esterified glyceride fraction into:
(1) a first fraction of the ethyl-esterified glyceride fraction comprising more docosahexaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying and comprising less eicosapentaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying;
and
(2) a second fraction of the ethyl-esterified glyceride fraction comprising more eicosapentaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying and comprising less docosahexaenoic acid ethyl ester than the ethyl-esterified glyceride fraction prior to the step (d) of purifying;
(e) purifying and fractionating the ethyl-esterified free fatty acid fraction into:
(3) a first fraction of the ethyl-esterified free fatty acid fraction comprising more docosahexaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying and comprising less eicosapentaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying;
and
(4) a second fraction of the ethyl-esterified free fatty acid fraction comprising more eicosapentaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying and comprising less docosahexaenoic acid ethyl ester than the ethyl-esterified free fatty acid fraction prior to the step (e) of purifying;
(f) mixing the fraction (1) of step (d) with the fraction (3) of step (e) to obtain a first mixture;
(g) mixing the fraction (2) of step (d) with the fraction (4) of step (e) to obtain a second mixture;
(h) further purifying the first mixture of step (f) to obtain a purified substance comprising a docosahexaenoic acid ethyl ester;
and
(i) further purifying the second mixture of step (g) to obtain a purified substance comprising an eicosapentaenoic acid ethyl ester.

13 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/914,804Filed 18 Aug 2014
Priority: JP 2013-17976930 Aug 2013
Published: US 2016/0208296 A121 Jul 2016
Granted: 26 Mar 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification19 codes

C12P 7/6432
Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone: eicosapentaenoic acids [EPA]
C07C 67/03
Preparation of carboxylic acid esters: by reacting an ester group with a hydroxy group
C07C 67/08
Preparation of carboxylic acid esters: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
C07C 67/54
By change in the physical state, e.g. crystallisation: by distillation