# US 11,898,120 B2 · Composition containing highly unsaturated fatty acid or alkyl ester thereof and a method for producing the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,898,120 B2
- Document ID: US11898120B2
- Status: Granted
- Kind: B2
- Application number: 17/962,984
- Filed: 2022-10-10
- Published: 2023-02-23
- Granted: 2024-02-13
- Earliest claimed: 2018-12-12
- Assignees: Nissui Corporation
- Applicants: Nissui Corporation
- Inventors: Nobushige Doisaki; Kiyomi Furihata; Hideaki Yamaguchi
- Web page: https://patentgrep.com/patent/US11898120B2

## CPC

- C11C 3/10: Ester interchange
- A23D 9/02: characterised by the production or working-up
- C11B 1/06: by pressing
- C11B 3/00: Refining fats or fatty oils
- C11B 3/12: by distillation
- C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)}
- B01D 3/12: Molecular distillation
- B01D 3/143: {by two or more of a fractionation, separation or rectification step}
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- A23D: EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS (preservation thereof A23B20/00; production, refinement or preservation of animal or vegetable fats or oils C11B, C11C)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)

## Abstract

PROBLEM To provide a composition comprising highly enriched PUFA or its alkyl esters while containing fatty acid esters of 3-MCPD at adequately low concentrations and to provide an efficient method for producing the composition. 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.

## Claims

### Claim 1

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) distilling the composition resulting from step (1) and collecting the main distillate fraction, thereby obtaining a composition comprising 50% by weight or more of fatty acid or fatty acid alkyl esters, wherein the concentration of 3-MCPD as found upon analyzing the main distillate fraction by American Oil Chemists' Society official method Cd 29b-13 assay A is less than 1.80 ppm.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the composition resulting from step (1) is subjected to at least one step selected from (a)-(c) prior to step (2):
(a) reducing a monoacyl glycerol concentration in the composition prepared in step (1) to less than 10,000 ppm, wherein 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.

### Claim 3 (depends on 2)

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

### Claim 4 (depends on 1)

The method according to claim 1, wherein distillation in step (2) is rectification.

### Claim 5 (depends on 2)

The method according to claim 2, 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 (a).

### Claim 6 (depends on 1)

The method 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.

### Claim 7 (depends on 1)

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