FR3073231B1 - ENZYMATIC PROCESS FOR THE FORMATION OF ESTOLIDES - Google Patents

ENZYMATIC PROCESS FOR THE FORMATION OF ESTOLIDES Download PDF

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Publication number
FR3073231B1
FR3073231B1 FR1760513A FR1760513A FR3073231B1 FR 3073231 B1 FR3073231 B1 FR 3073231B1 FR 1760513 A FR1760513 A FR 1760513A FR 1760513 A FR1760513 A FR 1760513A FR 3073231 B1 FR3073231 B1 FR 3073231B1
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France
Prior art keywords
estolides
formation
estolid
reaction medium
addition
Prior art date
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FR1760513A
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French (fr)
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FR3073231A1 (en
Inventor
Audrey Robic
Pascal Auffray
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PROD CHIM AUXILIAIRES ET DE SYNTHESE
Produits Chimiques Auxiliaires et de Synthese
Original Assignee
PROD CHIM AUXILIAIRES ET DE SYNTHESE
Produits Chimiques Auxiliaires et de Synthese
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Application filed by PROD CHIM AUXILIAIRES ET DE SYNTHESE, Produits Chimiques Auxiliaires et de Synthese filed Critical PROD CHIM AUXILIAIRES ET DE SYNTHESE
Priority to FR1760513A priority Critical patent/FR3073231B1/en
Priority to PCT/EP2018/080671 priority patent/WO2019092137A1/en
Priority to EP18796958.9A priority patent/EP3707268A1/en
Publication of FR3073231A1 publication Critical patent/FR3073231A1/en
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C12P7/625—Polyesters of hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C12Y301/01003—Triacylglycerol lipase (3.1.1.3)

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne un procédé pour la formation d'estolides à partir d'acides gras hydroxylés caractérisé en ce qu'il est conduit en présence d'une lipase de Streptomyces avermitilis, avantageusement sans solvant, de façon rapide, efficace et avec un nombre d'estolides EN élevé, voire avantageusement supérieur à 1,1. Optionnellement la fonction acide terminale de l'estolide peut être protégée par l'ajout d'un alcool au milieu réactionnel, suivi optionnellement de l'ajout d'un acide organique au milieu réactionnel pour protéger la fonction hydroxyle terminale de l'estolide, par un procédé monotope.The invention relates to a process for the formation of estolides from hydroxylated fatty acids, characterized in that it is carried out in the presence of a lipase from Streptomyces avermitilis, advantageously without solvent, quickly, efficiently and with a number of high EN estolides, or even advantageously greater than 1.1. Optionally, the terminal acid function of the estolid can be protected by the addition of an alcohol to the reaction medium, optionally followed by the addition of an organic acid to the reaction medium in order to protect the terminal hydroxyl function of the estolid, by a monotopic process.

FR1760513A 2017-11-08 2017-11-08 ENZYMATIC PROCESS FOR THE FORMATION OF ESTOLIDES Active FR3073231B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR1760513A FR3073231B1 (en) 2017-11-08 2017-11-08 ENZYMATIC PROCESS FOR THE FORMATION OF ESTOLIDES
PCT/EP2018/080671 WO2019092137A1 (en) 2017-11-08 2018-11-08 Enzymatic method for forming estolides
EP18796958.9A EP3707268A1 (en) 2017-11-08 2018-11-08 Enzymatic method for forming estolides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1760513 2017-11-08
FR1760513A FR3073231B1 (en) 2017-11-08 2017-11-08 ENZYMATIC PROCESS FOR THE FORMATION OF ESTOLIDES

Publications (2)

Publication Number Publication Date
FR3073231A1 FR3073231A1 (en) 2019-05-10
FR3073231B1 true FR3073231B1 (en) 2020-07-17

Family

ID=61003177

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1760513A Active FR3073231B1 (en) 2017-11-08 2017-11-08 ENZYMATIC PROCESS FOR THE FORMATION OF ESTOLIDES

Country Status (3)

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EP (1) EP3707268A1 (en)
FR (1) FR3073231B1 (en)
WO (1) WO2019092137A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT202000018148A1 (en) 2020-07-27 2020-10-27 Antonino Biundo Polyesters derived from unsaturated fatty acids and method for their production
CN117737146B (en) * 2023-12-20 2024-06-18 广东省农业科学院蚕业与农产品加工研究所 Glyceride type fatty acid hydroxy fatty acid ester and preparation method thereof

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2785978A (en) 1951-04-10 1957-03-19 Lever Brothers Ltd Surface active compounds and method for the production thereof
US4582804A (en) 1985-07-09 1986-04-15 Litchfield John H Microbiological synthesis of hydroxy-fatty acids and keto-fatty acids
AU7556591A (en) 1990-03-21 1991-10-21 United States of America, as represented by the Secretary, U.S. Department of Commerce, The Microbial production of a novel compound 7,10-dihydroxy-8-octadecenoic acid from oleic acid
US5380894A (en) 1991-03-01 1995-01-10 The United States Of America As Represented By The Secretary Of Agriculture Production of hydroxy fatty acids and estolide intermediates
US5852196A (en) 1997-03-11 1998-12-22 The United States Of America As Represented By The Secretary Of The Agriculture 12,13,17-trihydroxy-9(z)-octadeoenoic acid and derivatives and microbial isolate for production of the acid
MY139591A (en) 2004-02-26 2009-10-30 Univ Putra Malaysia Process for producing wax ester from dihydroxy fatty acid
JP5373399B2 (en) 2006-09-06 2013-12-18 学校法人慶應義塾 Ricinoleic acid-based polyester composition and process for producing the same
ES2300197B1 (en) 2006-09-15 2009-05-01 Universidad De Barcelona PROCEDURE OF OBTAINING POLYGYRICOLOLATE POLYGYLEROLATE.
FR2906530B1 (en) 2006-09-29 2012-02-17 Stearinerie Dubois Fils PROCESS FOR THE SYNTHESIS OF ESTOLID ESTERS
EP2213694B9 (en) * 2007-09-04 2013-10-09 Keio University 12-hydroxystearic acid copolymer and method for producing the same
FR2942628B1 (en) 2009-03-02 2011-07-01 Arkema France PROCESS FOR PRODUCING RICINOLEIC ACID ESTER BY SELECTIVE ENZYMATIC TRANSESTERIFICATION
EP2480642A1 (en) 2009-09-24 2012-08-01 Dow Global Technologies LLC Estolide compositions having excellent low temperature properties
US20130065970A1 (en) 2011-07-08 2013-03-14 Jakob BREDSGUARD Compositions and products containing estolide compounds
WO2013037017A1 (en) 2011-09-14 2013-03-21 Petróleo Brasileiro S.A. - Petrobras Enzymatic process for the synthesis of estolides
GB201505178D0 (en) 2015-03-26 2015-05-13 Stichting Dienst Landbouwkundi Production of fatty acid estolides

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Publication number Publication date
EP3707268A1 (en) 2020-09-16
WO2019092137A1 (en) 2019-05-16
FR3073231A1 (en) 2019-05-10

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