WO2003046114A8 - Method for commercial preparation of conjugated linoleic acid using spent alkali transesterification catalyst - Google Patents

Method for commercial preparation of conjugated linoleic acid using spent alkali transesterification catalyst

Info

Publication number
WO2003046114A8
WO2003046114A8 PCT/CA2002/001551 CA0201551W WO03046114A8 WO 2003046114 A8 WO2003046114 A8 WO 2003046114A8 CA 0201551 W CA0201551 W CA 0201551W WO 03046114 A8 WO03046114 A8 WO 03046114A8
Authority
WO
WIPO (PCT)
Prior art keywords
linoleic acid
conjugated linoleic
transesterification catalyst
commercial preparation
spent alkali
Prior art date
Application number
PCT/CA2002/001551
Other languages
French (fr)
Other versions
WO2003046114A3 (en
WO2003046114A2 (en
Inventor
J Reaney Martin
Original Assignee
Canada Majesty In Right Of
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 Canada Majesty In Right Of filed Critical Canada Majesty In Right Of
Priority to AU2002336832A priority Critical patent/AU2002336832A1/en
Priority to CA002466911A priority patent/CA2466911A1/en
Publication of WO2003046114A2 publication Critical patent/WO2003046114A2/en
Publication of WO2003046114A3 publication Critical patent/WO2003046114A3/en
Publication of WO2003046114A8 publication Critical patent/WO2003046114A8/en

Links

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
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • 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
    • C11C1/08—Refining
    • 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
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Abstract

Conjugated linoleic acid is readily prepared by mixing crude alkaline glycerol solution derived as a byproduct of triglyceride transesterification and a linoleate rich triglyceride, ester, soap, phospholipid, fatty acid, or wax and heating the mixture sufficiently to conjugate the linoleate double bonds. The reaction produces a favourable isomer mixture enriched in 10, 12-trans,cis octadecadienoic and 9,11- cis, trans-octadecadienoic acids.
PCT/CA2002/001551 2001-11-27 2002-10-10 Method for commercial preparation of conjugated linoleic acid using spent alkali transesterification catalyst WO2003046114A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002336832A AU2002336832A1 (en) 2001-11-27 2002-10-10 Method for commercial preparation of conjugated linoleic acid using spent alkali transesterification catalyst
CA002466911A CA2466911A1 (en) 2001-11-27 2002-10-10 Method for commercial preparation of conjugated linoleic acid using spent alkali transesterification catalyst

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/994,061 2001-11-27
US09/994,061 US6409649B1 (en) 2001-11-27 2001-11-27 Method for commercial preparation of conjugated linoleic acid using recycled alkali transesterification catalyst

Publications (3)

Publication Number Publication Date
WO2003046114A2 WO2003046114A2 (en) 2003-06-05
WO2003046114A3 WO2003046114A3 (en) 2003-09-04
WO2003046114A8 true WO2003046114A8 (en) 2003-10-16

Family

ID=25540250

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2002/001551 WO2003046114A2 (en) 2001-11-27 2002-10-10 Method for commercial preparation of conjugated linoleic acid using spent alkali transesterification catalyst

Country Status (4)

Country Link
US (1) US6409649B1 (en)
AU (1) AU2002336832A1 (en)
CA (1) CA2466911A1 (en)
WO (1) WO2003046114A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6409649B1 (en) * 2001-11-27 2002-06-25 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture & Agri-Food Canada Method for commercial preparation of conjugated linoleic acid using recycled alkali transesterification catalyst
CA2436650A1 (en) * 2003-08-06 2005-02-06 Naturia Inc. Conjugated linolenic acid (clnatm) compositions: synthesis, purification and uses
US7767713B2 (en) * 2004-08-05 2010-08-03 Palo Alto Investors Linoleic acid active agents for enhancing probability of becoming pregnant
US20090178928A1 (en) * 2007-06-29 2009-07-16 Archer-Daniels-Midland Company Process for Desalting Glycerol Solutions and Recovery of Chemicals
KR101087275B1 (en) * 2007-10-02 2011-12-05 대한민국(농촌진흥청장) Method of preparing conjugated linoleic acid from bio diesel byproduct and composition comprising thereof
CN102229527B (en) * 2009-12-14 2016-05-04 脂质营养品有限公司 Process
US11073522B2 (en) 2016-10-03 2021-07-27 Lincoln Memorial University Structural validation of very long chain dicarboxylic acids

Family Cites Families (25)

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Publication number Priority date Publication date Assignee Title
US2389260A (en) 1945-11-20 Producing unsaturated compounds
US2350583A (en) 1944-06-06 Drying oils
US2242230A (en) 1941-05-20 Process of producing conjugation in
US2343644A (en) 1941-07-30 1944-03-07 Distillation Products Inc Procedure for the preparation of substances containing conjugated double bonds
US4376711A (en) 1977-04-27 1983-03-15 Exxon Research And Engineering Co. Lubricant composition
US4164505A (en) 1977-07-08 1979-08-14 Sylvachem Corporation Flow process for conjugating unconjugated unsaturation of fatty acids
FR2474310A1 (en) 1980-01-25 1981-07-31 Oreal STABLE SOLUTION WITH OXIDATION OF VITAMIN F AND JOJOBA OIL AND COSMETIC COMPOSITIONS CONTAINING THE SAME
DE3019963A1 (en) 1980-05-24 1981-12-03 Henkel KGaA, 4000 Düsseldorf METHOD FOR CONJUGATING MULTIPLE UNSATURATED FATTY ACIDS AND FATTY ACID MIXTURES
US5070104A (en) 1989-02-17 1991-12-03 Wisconsin Alumni Research Foundation Methods of chelating metal and novel compositions therefor
SE9001245L (en) * 1990-04-05 1991-10-06 Carl Johan Lindquist FOERESTRINGSPROCESS
US5053534A (en) 1990-10-11 1991-10-01 Westvaco Corporation Process for making a dicarboxylic acid
US5194640A (en) 1991-06-10 1993-03-16 Westvaco Corporation Process for making high-purity oleic acid
US5430066A (en) 1992-04-29 1995-07-04 Wisconsin Alumni Research Foundation Methods for preventing weight loss, reduction in weight gain, and anorexia due to immune stimulation
US5554646A (en) 1992-04-29 1996-09-10 Wisconsin Alumni Research Foundation Method for reducing body fat in animals
US5674901A (en) 1995-06-01 1997-10-07 Wisconsin Alumni Research Foundation Methods of treating animals to maintain or increase CD-4 and CD-8 cell populations
US5504114A (en) 1992-04-29 1996-04-02 Wisconsin Alumni Research Foundation Method for controlling bird populations
US5428072A (en) 1992-04-29 1995-06-27 Wisconsin Alumni Research Foundation Method of increasing the efficiency of feed conversion in animals
US5585400A (en) 1996-02-27 1996-12-17 Wisconsin Alumni Research Foundation Methods of attenuating the allergic response in animals
US5760083A (en) 1996-08-07 1998-06-02 Wisconsin Alumni Research Foundation Use of CLA to reduce the incidence of valgus and varus leg deforomities in poultry
JP3017108B2 (en) * 1996-10-30 2000-03-06 リノール油脂株式会社 Method for producing conjugated linoleic acid
US5892074A (en) 1997-02-18 1999-04-06 Seidel; Michael C. Synthesis of conjugated linoleic acid (CLA)
US5770217A (en) 1997-07-02 1998-06-23 Atlatl, Inc. Dietary supplement for hematological, immune and appetite enhancement
US6420577B1 (en) * 1999-12-01 2002-07-16 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture Method for commercial preparation of conjugated linoleic acid
AU2001226597A1 (en) * 2000-01-12 2001-07-24 Her Majesty In Right Of Canada As Represented By The Minister Of Agriculture Method for commercial preparation of preferred isomeric forms of ester free conjugated fatty acids with solvent systems containing polyether alcohol solvents
US6409649B1 (en) * 2001-11-27 2002-06-25 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture & Agri-Food Canada Method for commercial preparation of conjugated linoleic acid using recycled alkali transesterification catalyst

Also Published As

Publication number Publication date
AU2002336832A8 (en) 2003-06-10
WO2003046114A3 (en) 2003-09-04
US6409649B1 (en) 2002-06-25
AU2002336832A1 (en) 2003-06-10
WO2003046114A2 (en) 2003-06-05
CA2466911A1 (en) 2003-06-05

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