# US 10,119,098 B2 · Concentration of fatty acid alkyl esters by enzymatic reactions with glycerol > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,119,098 B2 - Document ID: US10119098B2 - Status: Granted - Kind: B2 - Application number: 11/438,833 - Filed: 2006-05-23 - Published: 2006-12-21 - Granted: 2018-11-06 - Earliest claimed: 2005-05-23 - Assignees: Epax Norway AS - Applicants: Per Christian Saebo; Inge Bruheim; Daniele Mancinelli; Asgeir Saebo - Inventors: Per Christian Saebo; Inge Bruheim; Daniele Mancinelli; Asgeir Saebo - Web page: https://patentgrep.com/patent/US10119098B2 ## CPC - C11C 3/06: with glycerol - A23D 9/013: Other fatty acid esters, e.g. phosphatides - A23K 20/158: Fatty acids; Fats; Products containing oils or fats - A23L 29/04: {Fatty acids or derivatives} - A23L 33/12: Fatty acids or derivatives thereof - C11C 1/005: {Splitting up mixtures of fatty acids into their constituents (processes intended for both fats and fatty acids C11B7/00)} - C11C 3/02: by esterification of fatty acids with glycerol - 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) - A23K: FODDER - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) ## Abstract An enzymatic process for the kinetic separation of alkyl esters under organic solvent free conditions is disclosed. Alkyl esters obtained from e.g. fish oil are reacted with glycerol, in the presence of water, at different rates in an evacuated chamber. The reaction is terminated prior to reaching equilibrium and the enriched alkyl ester fraction is isolated from the reaction mixture by short path distillation. ## Claims ### Claim 1 A method of obtaining a fatty acid ester composition having an increased concentration of at least one alkyl ester, and formulating the same, the method comprising the steps: (a) combining (1) an initial fatty acid ester composition comprising a plurality of different fatty acid esters each at an initial concentration, wherein the plurality of different fatty acid esters comprises at least one alkyl ester selected from the group consisting of cis-6,9,12 octadecatrienoic (GLA) ethyl ester and docosahexaenoic acid (DHA) alkyl ester, (2) glycerol and (3) a catalytically effective amount of an enzyme, to form a mixture, wherein the enzyme is rhizomucor miehei lipase; (b) subjecting the mixture to reaction conditions under reduced pressure of between about 0.1-1.0 mbar and in the presence of water, wherein the water is added as water vapor such that the at least one alkyl ester esterifies with the glycerol at a lower rate as compared to other fatty acid esters in the initial fatty acid ester composition, to provide reaction products comprising (1) a glyceride composition and (2) a modified fatty acid ester composition comprising the at least one alkyl ester, wherein the at least one alkyl ester is present in the modified fatty acid ester composition at a concentration that is at least 11 percentage points more than an initial concentration of the at least one alkyl ester in the initial fatty acid ester composition; (c) separating the modified fatty acid ester composition from the glyceride composition; and (d) formulating the modified fatty acid ester composition as a food product, a feed product, a food supplement or a pharmaceutical product suitable for consumption by an animal or a human. ### Claim 2 (depends on 1) The method of claim 1, wherein the reaction is terminated after a desired concentration of the at least one alkyl ester is reached. ### Claim 3 (depends on 1) The method of claim 1, wherein the reaction conditions comprise agitating the mixture at temperatures between 25° C. and 50° C. ### Claim 4 (depends on 1) The method of claim 1, wherein the separating step comprises short path distillation. ### Claim 5 (depends on 1) The method of claim 1, wherein the separating step comprises removing volatile reaction products from the mixture. ### Claim 6 (depends on 1) The method of claim 1, wherein the fatty acid ester composition is derived from one or more oils selected from the group consisting of fish oil, algae oil, castor oil, evening primrose oil, borage oil, seal oil and whale oil. ### Claim 7 (depends on 1) The method of claim 1, wherein the fatty acid ester composition is derived from fish oil. ### Claim 8 (depends on 1) The method of claim 1, wherein the mixture further comprises a stabilizer. ### Claim 9 (depends on 1) The method of claim 1, wherein the initial fatty acid ester composition and the glycerol are present in the mixture at an initial fatty acid ester composition:glycerol ratio of about 5:1 to about 8:1. ### Claim 10 (depends on 1) The method of claim 1, wherein said formulating step comprises formulating the modified fatty acid ester composition as a food supplement or a pharmaceutical product suitable for consumption by a human. ### Claim 11 A method of obtaining a fatty acid ester composition having an increased concentration of at least one alkyl ester, formulating and consuming of the same, the method comprising the steps: (a) combining (1) an initial fatty acid ester composition comprising a plurality of different fatty acid esters each at an initial concentration, wherein the plurality of different fatty acid esters comprises at least one alkyl ester selected from the group consisting of cis-6,9,12 octadecatrienoic (GLA) ethyl ester and docosahexaenoic acid (DHA) alkyl ester, or (2) glycerol and (3) a catalytically effective amount of an enzyme, to form a mixture, wherein the enzyme is rhizomucor miehei lipase; (b) subjecting the mixture to reaction conditions under reduced pressure of between about 0.1-1.0 mbar and in the presence of water, wherein the water is added as water vapor such that the at least one alkyl ester esterifies with the glycerol at a lower rate as compared to other fatty acid esters in the initial fatty acid ester composition, to provide reaction products comprising (1) a glyceride composition and (2) a modified fatty acid ester composition comprising the at least one alkyl ester, wherein the at least one alkyl ester is present in the modified fatty acid ester composition at a concentration that is at least 11 percentage points more than an initial concentration of the at least one alkyl ester in the initial fatty acid ester composition; (c) separating the modified fatty acid ester composition from the glyceride composition; (d) formulating the modified fatty acid ester composition as a pharmaceutical product suitable for consumption by a human; and (e) consuming of the pharmaceutical product by a human. ### Claim 12 (depends on 11) The method of claim 11, wherein the reaction conditions comprise agitating the mixture at temperatures between 25° C. and 50° C. ### Claim 13 (depends on 11) The method of claim 11, wherein the separating step comprises removing volatile reaction products from the mixture. ### Claim 14 (depends on 11) The method of claim 11, wherein the fatty acid ester composition is derived from one or more oils selected from the group consisting of fish oil, algae oil, castor oil, evening primrose oil, borage oil, seal oil and whale oil. ### Claim 15 (depends on 11) The method of claim 11, wherein the fatty acid ester composition is derived from fish oil. ### Claim 16 (depends on 11) The method of claim 11, wherein the mixture further comprises a stabilizer. ### Claim 17 (depends on 11) The method of claim 11, wherein the initial fatty acid ester composition and the glycerol are present in the mixture at an initial fatty acid ester composition:glycerol ratio of about 5:1 to about 8:1.