# US 2012/0083616 A1 · Method for producing a concentrate of eicosapentaenoic and docosahexaenoic acid esters

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

- Number: US 2012/0083616 A1
- Document ID: US20120083616A1
- Status: Published application
- Kind: A1
- Application number: 13/375,030
- Filed: 2010-06-01
- Published: 2012-04-05
- Earliest claimed: 2009-06-02
- Assignees: Golden Omega S.A.
- Inventors: Tomas Francis Harting Glade; Miguel Angel Diaz Fuenzalida; Alejandro Markovits Rojas
- Web page: https://patentgrep.com/patent/US20120083616A1

## CPC

- C11C 1/025: {by saponification and release of fatty acids}
- A23D 9/02: characterised by the production or working-up
- C11B 3/006: {by extraction}
- C11B 3/04: with acids
- C11B 3/06: with bases
- C11C 1/08: Refining
- C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)}
- 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)

## Abstract

The current invention describes processes for obtaining of concentrates of esters of eicosapentaenoic acid and docosahexaenoic acid for their use in massive and regular human consumption either as a pharmaceutical ingredient or as a food ingredient, which are characterized by having neutral and stable organoleptic properties, free of side effects, which are typical from marine oils derivatives, and with low content of Persistent Organic Pollutants (POP).

## Claims

### Claim 1

Process for obtaining a concentrate of esters of EPA and DHA from crude or refined marine oils, which comprises:
a) contacting crude or refined marine oil with at least one alkali and water at a temperature no higher than 100° C. to obtain a mixture comprising saponified marine oil;
b) contacting the saponified mixture with at least one organic solvents to form a refined phase comprising alkaline salts of fatty acids and an extracted phase;
c) separating the extracted phase from the refined phase;
d) mixing the refined phase with an aqueous solution of an acid to form a non aqueous phase comprising fatty acids and an aqueous phase;
e) separating the aqueous phase of the non-aqueous phase;
f) mixing the separated non aqueous phase with an alcohol and an esterification catalyst at a temperature of at most 150° C. until an esterified mixture comprising esters of fatty acids is obtained;
g) removing the catalyst from the esterified mixture to obtain the catalyst-free esterified mixture;
h) removing any solvents from the catalyst-free esterified mixture to obtain esters of fatty acids, and
i) distilling the esters of fatty acids in a short path distillation column at a temperature of at most 180° C. and a pressure of less than 1 mbar to obtain a concentrate comprising esters of EPA and DHA.

### Claim 2 (depends on 1)

Process according to claim 1, wherein the alkali in step (a) is chosen from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, magnesium hydroxide and mixtures thereof, the weight ratio of alkali to crude or refined oil is approximately 0.15:1, and the weight ratio of water to crude or refined oil is between 0.5:1 and 2:1.

### Claim 3 (depends on 1)

Process according to claim 1, wherein the mixture of step (a) comprises ethanol and the weight ratio of ethanol to crude oil or refined is between 0.5:1 and 2:1.

### Claim 4 (depends on 1)

Process according to claim 1, wherein the mixture of step (a) comprises hexane and the weight ratio of hexane to crude or refined oil is between 0.5:1 and 2:1.

### Claim 5 (depends on 1)

Process according to claim 1, wherein the mixture of step (a) comprises one or more antioxidants and the weight ratio of antioxidant to crude or refined oil is less than 1:100.

### Claim 6 (depends on 1)

Process according to claim 1, wherein the mixture of step (a) is maintained at a pressure of approximately 1 bar and at a temperature of not more than 100° C. during a period of time between 30 and 120 minutes to obtain saponified marine oil.

### Claim 7 (depends on 1)

Process according to claim 1, wherein in step (b) the temperature is between 20 to 60° C., the pressure is approximately 1 bar, the solvent used is chosen from the group consisting of petroleum ether, pentane, hexane, heptane and octane and the weight ratio of solvent to be reacted is between 1:1 and 5:1.

### Claim 8 (depends on 1)

Process according to claim 1, wherein in step (d) the acid is chosen from the group consisting of sulfuric acid, phosphoric acid, acetic acid, formic acid, trichloroacetic acid and carbonic acid, the temperature is between 20 and 70° C., the pressure is about 1 bar and that stoichiometric ratio of the acid to alkali used in step (a) is approximately 1.05:1.

### Claim 9 (depends on 1)

Process according to claim 1, wherein the alcohol of step (f) is chosen from the group consisting of methanol, ethanol and glycerol, the temperature is between 30 and 80° C., the pressure approximately 1 bar and the esterifying mixture is maintained at a temperature between 30 and 80° C. during a time between 60 and 240 minutes to form the esterified mixture.

### Claim 10 (depends on 1)

Process according to claim 1, wherein the esters of fatty acid are distilled at a pressure lower than 0.1 mbar and a temperature less than 150° C.

### Claim 11 (depends on 10)

A concentration of esters of EPA and DHA obtained according to the process of claim 10, wherein the total content of esters of EPA and DHA is at least 40% by weight of the concentrate, the content of trans isomers of the concentrates is equal to or lower than the content of trans isomers of the crude or refined marine oil, the concentrates have neutral organoleptic properties, oxidative stability, and contain less than 90 ng/g of PCB's and less then 2 pg/g of concentrate of dioxins and furans.