WO2011095284A1 - Enrichissement d'acides gras polyinsaturés - Google Patents

Enrichissement d'acides gras polyinsaturés Download PDF

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Publication number
WO2011095284A1
WO2011095284A1 PCT/EP2011/000259 EP2011000259W WO2011095284A1 WO 2011095284 A1 WO2011095284 A1 WO 2011095284A1 EP 2011000259 W EP2011000259 W EP 2011000259W WO 2011095284 A1 WO2011095284 A1 WO 2011095284A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
salt solution
acid salt
salts
fatty acids
Prior art date
Application number
PCT/EP2011/000259
Other languages
German (de)
English (en)
Inventor
Peter Horlacher
Dieter Hietsch
Thomas Rosen
Jörg SCHWARZER
Ulrich SCHÖRKEN
Original Assignee
Cognis Ip Management Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Ip Management Gmbh filed Critical Cognis Ip Management Gmbh
Publication of WO2011095284A1 publication Critical patent/WO2011095284A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • 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
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/005—Splitting up mixtures of fatty acids into their constituents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • 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
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents

Definitions

  • the present invention relates to a process for the enrichment of polyunsaturated fatty acids (PUFA), in particular EPA and / or DHA. Furthermore, the present invention relates to a composition containing 0.1 to 1 GC area% saturated fatty acids (SAFA) and at least 70 GC area% PUFA.
  • PUFA polyunsaturated fatty acids
  • SAFA saturated fatty acids
  • Polyunsaturated fatty acids are fatty acids containing at least two double bonds. These include, for example, linoleic acid, alpha-linolenic acid, gamma-linolenic acid and arachidonic acid. Polyunsaturated fatty acids have at least five carbon atoms. In the following, polyunsaturated fatty acids are understood in particular to mean those which have at least six C atoms. Omega-3 fatty acids are also among the polyunsaturated fatty acids. EPA and DHA are special omega-3 fatty acids.
  • EPA is the abbreviation for (5Z, 8Z, 11Z, 14Z, 17Z) -eicosa-5,8, 11,14,17-pentaenoic acid.
  • DHA is the abbreviation for (4Z, 7Z, 10Z, 13Z, 16Z, 19Z) docosa-4,7, 10,13,16,19-hexaenoic acid.
  • Polyunsaturated fatty acids can be used as ingredients of foods, in dietary supplements or in functional foods. They can also be used in the pharmaceutical sector, for example in the case of EPA and DHA for the therapy or prophylaxis of coronary heart disease. They are usually used as glycerol esters, ie as part of fats. But you can also as free fatty acids or in the form of esters, eg. As ethyl esters, are used.
  • Polyunsaturated fatty acids especially EPA and DHA may be derived from natural sources, e.g. B. from fish oil, are obtained.
  • natural sources e.g. B. from fish oil
  • processes for the enrichment of polyunsaturated fatty acids, in particular of EPA and / or of DHA are required, by means of which polyunsaturated fatty acids, in particular EPA and / or DHA natural sources such.
  • B. fish oil can be enriched.
  • DE 969103 discloses the accumulation of EPA and DHA from solid sodium soaps by using organic solvents in which the sodium soaps are not soluble but the other adjunct substances.
  • GB 719 513 discloses a process in which soaping of fats and oils gives soaps which in turn are converted into solid substances. Then the unsaturated soaps are dissolved with water-miscible organic solvents. A two-stage crystallization with two crystallization stages at different temperatures is not disclosed.
  • WO 2009/020406 discloses a crystallization process for the enrichment of PUFA. However, no two-step process with two crystallization stages at different temperatures is disclosed.
  • the object of the present invention is to provide a process for the enrichment of polyunsaturated fatty acids and to provide a composition obtainable by this process.
  • Providing a first fatty acid salt solution in a solvent may be accomplished by contacting a mixture of free fatty acids with a solvent and a sodium or lithium base.
  • This provision may also be such that a compound of the fatty acids, e.g. As an ester, in particular an ester glycerol or an ester with ethanol, with a solvent and a sodium or a lithium base are brought into contact.
  • a compound of the fatty acids e.g. As an ester, in particular an ester glycerol or an ester with ethanol
  • hydrolysis of the esters to the fatty acid salts takes place.
  • the process according to the invention makes it possible to produce highly enriched EPA and / or DHA products starting from fish oils.
  • the products produced by the process according to the invention can be used in the pharmaceutical sector in the dietary supplement market and as so-called "infant nutrition" for child nutrition.
  • the method according to the invention has many advantages.
  • An advantage is that even at crystallization temperatures of -18 ° C or above, a significant accumulation of polyunsaturated fatty acids can be achieved.
  • the proportion of saturated fatty acids can be reduced to a content of less than 4% (crystallization at Room temperature, ie at 23 ° C) or less than 1% (crystallization at -18 ° C) can be reduced.
  • the crystallization is preferably carried out in the presence of an organic solvent, such as. As ethanol performed.
  • the weight ratio of solvent (preferably water-containing ethanol) to the lithium and / or sodium salts of the fatty acids (including the saturated and unsaturated fatty acids) is 2 to 1 to 4 to 1.
  • water-containing ethanol When water-containing ethanol is used as a solvent, its water content is preferably 3-10% by weight, more preferably 4-8% by weight.
  • the filter cake was then washed with 450 g of ethanol.
  • the filtrate was cooled to -18 ° C and stirred at -18 ° C for one hour.
  • the resulting precipitate was separated analogously to the first filtration and washed the filter cake.
  • the resulting filtrate was placed in a reaction flask and the solvent was removed in vacuo (25 mbar) at 40 ° C.
  • To the residue was added 750 g of deionized water and 220 g of phosphoric acid (75%). The mixture was heated to 70 ° C, stirred for 15 minutes and then allowed to stand for phase separation. After separating the aqueous phase, the organic phase was washed again with water. The free fatty acid was then dried in vacuo (25 mbar).
  • the filter cake was then washed with 450 g of ethanol.
  • the filtrate was cooled to -18 ° C and stirred at -18 ° C for one hour.
  • the precipitate was separated analogously to the first filtration and washed the filter cake.
  • the resulting filtrate was placed in a reaction flask and the solvent was removed in vacuo (25 mbar) at 40 ° C.
  • To the residue was added 750 g of deionized water and 220 g of phosphoric acid (75%).
  • the mixture was heated to 70 ° C, stirred for 15 minutes and then allowed to stand for phase separation. After separating the aqueous phase, the organic phase was rinsed again with water.
  • the free fatty acid was then dried in vacuo (25 mbar).
  • compositions of PUFA and SAFA in which the S AFA content is less than 1 area% (GC after ethylation of the free fatty acids, flame ionization detector FID), in particular 0.1 to 1 area% and PUFA content at.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé d'enrichissement d'acides gras polyinsaturés (PUFA), en particulier d'EPA et/ou de DHA. L'invention concerne également une composition contenant 0,1 à 1 % surfacique mesuré par chromatographie en phase gazeuse (GC) d'acides gras saturés (SAFA) et au moins 70 % surfacique (GC) de PUFA.
PCT/EP2011/000259 2010-02-02 2011-01-22 Enrichissement d'acides gras polyinsaturés WO2011095284A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10001000.8 2010-02-02
EP10001000 2010-02-02

Publications (1)

Publication Number Publication Date
WO2011095284A1 true WO2011095284A1 (fr) 2011-08-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/000259 WO2011095284A1 (fr) 2010-02-02 2011-01-22 Enrichissement d'acides gras polyinsaturés

Country Status (1)

Country Link
WO (1) WO2011095284A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8889895B2 (en) 2011-03-08 2014-11-18 Cognis Ip Management Gmbh Process for the distillation of fatty acid esters
US9050308B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
WO2015154997A1 (fr) * 2014-04-07 2015-10-15 Epax Norway As Composition d'acides gras mono-insaturés à chaine longue et son procédé de production
US9492545B2 (en) 2012-05-07 2016-11-15 Omthera Pharmaceuticals Inc. Compositions of statins and omega-3 fatty acids
CN115715559A (zh) * 2022-11-08 2023-02-28 嘉必优生物技术（武汉）股份有限公司 一种富集油脂中dha的方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB719513A (en) 1951-09-25 1954-12-01 Olav Notevarp Improved process for fractionating highly unsaturated fatty acids from less unsaturated and saturated fatty acids
DE969103C (de) 1951-09-25 1958-04-30 Amund Sletnes Verfahren zur Gewinnung von wertvollen Bestandteilen aus Fetten und OElen
GB824574A (en) 1956-07-09 1959-12-02 Canada Packers Ltd Process for the fractionation of fatty acid mixtures
US2934547A (en) * 1955-09-19 1960-04-26 Emery Industries Inc Method of separating fatty acids
EP1211304A2 (fr) * 2000-11-30 2002-06-05 Sepu Fine Chem Co., Ltd. Procédé d'isolation d'acides gras insaturés hautement purifiés par cristallisation
WO2009020406A1 (fr) 2007-08-07 2009-02-12 Granate Seed Limited Procédés de préparation de substances lipidiques, substances lipidiques ainsi produites et leurs utilisations
US20090163730A1 (en) * 2005-12-21 2009-06-25 Reaney Martin J T Process for the preparation of biodiesel

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB719513A (en) 1951-09-25 1954-12-01 Olav Notevarp Improved process for fractionating highly unsaturated fatty acids from less unsaturated and saturated fatty acids
DE969103C (de) 1951-09-25 1958-04-30 Amund Sletnes Verfahren zur Gewinnung von wertvollen Bestandteilen aus Fetten und OElen
US2934547A (en) * 1955-09-19 1960-04-26 Emery Industries Inc Method of separating fatty acids
GB824574A (en) 1956-07-09 1959-12-02 Canada Packers Ltd Process for the fractionation of fatty acid mixtures
EP1211304A2 (fr) * 2000-11-30 2002-06-05 Sepu Fine Chem Co., Ltd. Procédé d'isolation d'acides gras insaturés hautement purifiés par cristallisation
US20090163730A1 (en) * 2005-12-21 2009-06-25 Reaney Martin J T Process for the preparation of biodiesel
WO2009020406A1 (fr) 2007-08-07 2009-02-12 Granate Seed Limited Procédés de préparation de substances lipidiques, substances lipidiques ainsi produites et leurs utilisations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ACTA CHEMICA SCANDINAVIA, vol. 17, no. 10, 1963, pages 2622 - 2627
JAOCS, vol. 77, no. 4, 2000, pages 425 - 428
TOR-CHERN CHEN ET AL: "Enrichment of eicosapentaenoic acid and docosahexaenoic acid in saponified menhaden oil.", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 77, no. 4, 1 April 2000 (2000-04-01), pages 425 - 428, XP002588209, DOI: 10.1007/S11746-000-0068-7 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8889895B2 (en) 2011-03-08 2014-11-18 Cognis Ip Management Gmbh Process for the distillation of fatty acid esters
US9050308B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9050309B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US10117844B2 (en) 2012-01-06 2018-11-06 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9492545B2 (en) 2012-05-07 2016-11-15 Omthera Pharmaceuticals Inc. Compositions of statins and omega-3 fatty acids
WO2015154997A1 (fr) * 2014-04-07 2015-10-15 Epax Norway As Composition d'acides gras mono-insaturés à chaine longue et son procédé de production
CN106459829A (zh) * 2014-04-07 2017-02-22 艾帕克斯挪威联合股份有限公司 长链单不饱和脂肪酸组合物及其制备方法
EP3613833A1 (fr) 2014-04-07 2020-02-26 Epax Norway AS Composition d'acides gras monoinsaturés à longue chaîne et composition d'acides gras polyinsaturés à longue chaîne et son procédé de fabrication
CN106459829B (zh) * 2014-04-07 2020-03-06 艾帕克斯挪威联合股份有限公司 长链单不饱和脂肪酸组合物及其制备方法
CN115715559A (zh) * 2022-11-08 2023-02-28 嘉必优生物技术（武汉）股份有限公司 一种富集油脂中dha的方法

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