WO2009047444A1 - Procedes de synthese de diacides gras par metathese de diacides insatures obtenus par fermentation d'acides gras naturels - Google Patents
Procedes de synthese de diacides gras par metathese de diacides insatures obtenus par fermentation d'acides gras naturels Download PDFInfo
- Publication number
- WO2009047444A1 WO2009047444A1 PCT/FR2008/051664 FR2008051664W WO2009047444A1 WO 2009047444 A1 WO2009047444 A1 WO 2009047444A1 FR 2008051664 W FR2008051664 W FR 2008051664W WO 2009047444 A1 WO2009047444 A1 WO 2009047444A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- diacids
- unsaturated
- metathesis
- formula
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- 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
- 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
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/44—Polycarboxylic 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
Definitions
- the invention relates to a method of synthesis by cross metathesis of saturated or unsaturated diacids or saturated fatty diesters from a fatty acid or a natural monounsaturated fatty ester.
- the most well-known unsaturated diacids or diesters are those comprising chains containing from 4 to 6 carbon atoms, such as C 4 acids, maleic and fumaric acids, C 5 acids, citraconic, mesaconic and itaconic acids and C 6 acids, 2-methylene glutaric and muconic acids.
- C 4 acids maleic and fumaric acids
- C 5 acids citraconic
- mesaconic and itaconic acids and C 6 acids 2-methylene glutaric and muconic acids.
- dimers generally obtained by condensation of unsaturated carboxylic acids. The properties, syntheses and uses of these diacids are described in the Uhlmann Encyclopedia Vol. A8, pages 533-536.
- Another example is the cleavage of ricinoleic acid by the action of sodium hydroxide at a temperature above 180 ° C.
- This method used industrially makes it possible to obtain the diacid containing 10 carbon atoms.
- the same method, as illustrated in the diagram below, can be applied to lesquerolic acid and leads to the formation of a diacid with 12 carbon atoms.
- This method has the advantage of using renewable raw materials but is limited mainly to diacid C10, lesquerolic acid is still not widespread, and therefore this method is relatively little used.
- diacid-diamine type In the chemical industry and in particular that of polymers, such as the production of polyamides of diacid-diamine type or of technical polymers, it is necessary to have a whole range of saturated or unsaturated diacids. These diacids will be raw materials that can be further converted into diamines of the same chain length by simple chemical reaction. Unsaturated diacids will be used as monomers of specialty polymers.
- the term "diacid” will be used for the sake of clarity to indicate indifferently the diacid and the diester.
- the fatty acid can be treated either in its acid form or in its ester form. The transition from one form to another is simply by alcoholysis, esterification or hydrolysis.
- the proposed solution is to work from monounsaturated long-chain natural fatty acids which are oxidized by fermentation to diacids which are cross-metathesized with an acrylic-type compound.
- long-chain natural fatty acid is meant an acid derived from plant or animal media, including algae, more generally from the plant kingdom, and therefore renewable having at least 10 and preferably at least 14 carbon atoms per molecule.
- acids examples include C10 acids, obtusilic (cis-4-decenoic) and caproleic (cis-9-decenoic) acids, C12 acids, lauroleic acids (cis-5- dodecenoic) and linderic (cis-4-dodecenoic), C14 acids, myristoleic (cis-9-tetradecenoic), physeteric (cis-5-tetradecenoic) and tsuzuic (cis-4- tetradecenoic acid), C16 acid, palmitoleic acid (cis-9-hexadecenoic acid), C18 acids, oleic (cis-9-octadecenoic), elaidic (trans-9-octadecenoic), petroselinic (cis-9-hexadecenoic) 6-octadecenoic), vaccenic (cis-11-octadecenoic) and ricinoleic
- propylene is produced and is removed from the reaction medium.
- R 3 is CH 3
- the second step is illustrated by synthetic examples of short chain fatty acids are given below. All the mechanisms detailed below illustrate, to facilitate the presentation, the acid form. However, metathesis is also effective with an ester and is often more effective. In the same way, the diagrams illustrate reactions with the cis isomer of acids (or esters); the mechanisms are equally applicable to trans isomers.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08837762.7A EP2191003B1 (fr) | 2007-09-20 | 2008-09-17 | Procédés de synthèse de diacides gras par métathèse de diacides insaturés obtenus par fermentation d'acides gras naturels |
JP2010525401A JP6073044B2 (ja) | 2007-09-20 | 2008-09-17 | 天然脂肪酸の発酵で得られる不飽和二酸のメタセシスによる脂肪二酸の合成方法 |
US12/678,366 US9023626B2 (en) | 2007-09-20 | 2008-09-17 | Methods for the synthesis of fatty diacids by the metathesis of unsaturated diacids obtained by fermentation of natural fatty acids |
BRPI0816431-2A2A BRPI0816431A2 (pt) | 2007-09-20 | 2008-09-17 | Processo de síntese de diácidos ou diésteres |
CN200880116942A CN101868552A (zh) | 2007-09-20 | 2008-09-17 | 通过由天然脂肪酸发酵得到的不饱和二酸的复分解合成脂肪二酸的方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0757691A FR2921363B1 (fr) | 2007-09-20 | 2007-09-20 | Procedes de synthese de diacides gras par metathese de diacides insatures obtenus par fermentation d'acides gras naturels |
FR0757691 | 2007-09-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009047444A1 true WO2009047444A1 (fr) | 2009-04-16 |
Family
ID=39401187
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2008/051664 WO2009047444A1 (fr) | 2007-09-20 | 2008-09-17 | Procedes de synthese de diacides gras par metathese de diacides insatures obtenus par fermentation d'acides gras naturels |
Country Status (7)
Country | Link |
---|---|
US (1) | US9023626B2 (fr) |
EP (1) | EP2191003B1 (fr) |
JP (1) | JP6073044B2 (fr) |
CN (1) | CN101868552A (fr) |
BR (1) | BRPI0816431A2 (fr) |
FR (1) | FR2921363B1 (fr) |
WO (1) | WO2009047444A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014122410A2 (fr) | 2013-02-08 | 2014-08-14 | Arkema France | Synthese conjuguee d'un nitrile- ester/acide et d'un diester/diacide |
US20140235517A1 (en) * | 2011-02-13 | 2014-08-21 | Trent University | Esters for use as a base stock and in lubricant applications |
WO2014125223A1 (fr) | 2013-02-15 | 2014-08-21 | Arkema France | Utilisation de mercapto-esters methyliques en tant qu'agents de transfert de chaine |
US9382189B2 (en) | 2013-02-08 | 2016-07-05 | Arkema France | Synthesis of a branched unsaturated compound by means of cross metathesis |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5921194B2 (ja) * | 2009-01-15 | 2016-05-24 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | グルタコネートの製造方法 |
DE102010010984A1 (de) * | 2010-03-10 | 2011-09-15 | Emery Oleochemicals Gmbh | Verfahren zur Herstellung von Dicarbonsäuren oder Dicarbonsäureestern durch Metathese |
WO2012071439A1 (fr) * | 2010-11-22 | 2012-05-31 | The Regents Of The University Of California | Cellules hôtes et procédés pour produire des diacides |
FR2978147B1 (fr) | 2011-07-19 | 2015-01-09 | Arkema France | Procede de synthese d'acides omega-fonctionnalises a partir d'acides ou esters gras hydroxyles |
FR2992642B1 (fr) | 2012-06-29 | 2015-06-19 | Novance | Procede de synthese d’acides insatures biosources |
WO2014085393A1 (fr) | 2012-11-30 | 2014-06-05 | Elevance Renewable Sciences | Procédés de fabrication d'oléfines internes fonctionnalisées et leurs utilisations |
FI128953B (en) | 2019-09-26 | 2021-03-31 | Neste Oyj | Production of renewable chemicals including metathesis and microbial oxidation |
FI128954B (en) | 2019-09-26 | 2021-03-31 | Neste Oyj | Preparation of renewable base oil including metathesis |
FI128952B (en) | 2019-09-26 | 2021-03-31 | Neste Oyj | Preparation of renewable alkenes including metathesis |
US20230089404A1 (en) * | 2021-09-18 | 2023-03-23 | Indian Oil Corporation Limited | Bioassisted Process For Selective Conversion Of Alkane Rich Refinery Stream |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474882A (en) * | 1980-10-09 | 1984-10-02 | Daicel Chemical Industries, Ltd. | Microbiological process for the preparation of unsaturated dicarboxylic acids |
Family Cites Families (14)
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US3823070A (en) * | 1971-12-23 | 1974-07-09 | Hasegawa T Co Ltd | Process for producing a straight chain dicarboxylic acid,an omega-hydroxy fatty acid,and an omega-1-keto fatty acid |
JPS5543759B2 (fr) * | 1972-06-28 | 1980-11-07 | ||
JPS5592691A (en) | 1978-12-28 | 1980-07-14 | Baiorisaac Center:Kk | Purification of dicarboxylic acid produced by fermentation |
US5254466A (en) | 1989-11-06 | 1993-10-19 | Henkel Research Corporation | Site-specific modification of the candida tropicals genome |
JP2002535297A (ja) * | 1999-01-26 | 2002-10-22 | カリフォルニア インスティチュート オブ テクノロジー | 末端オレフィンのクロスメタセシスのための方法 |
DE19907519A1 (de) * | 1999-02-22 | 2000-08-31 | Basf Ag | Verfahren zur Herstellung von substituierten Olefinen |
MXPA01012033A (es) * | 1999-05-24 | 2002-11-04 | California Inst Of Techn | Catalizador de metatesis de metal-carbeno basado en inidazolidina. |
ATE239690T1 (de) * | 1999-08-05 | 2003-05-15 | Frische Gmbh | Verfahren zur gewinnung von gesättigten dicarbonsäuren aus der ozonolyse ungesättigter fettsäuren |
US6569670B2 (en) * | 1999-09-30 | 2003-05-27 | Cognis Corporation | Fermentation process |
IL149720A0 (en) * | 1999-11-18 | 2002-11-10 | Metathesis syntheses of pheremones or their components | |
US6660505B2 (en) * | 2000-06-22 | 2003-12-09 | Cognis Corporation | Isolation of carboxylic acids from fermentation broth |
US6777213B2 (en) * | 2002-10-29 | 2004-08-17 | Cognis Corporation | Isolation of carboxylic acids from fermentation broth |
FR2878246B1 (fr) * | 2004-11-23 | 2007-03-30 | Inst Francais Du Petrole | Procede de co-production d'olefines et d'esters par ethenolyse de corps gras insatures dans des liquides ioniques non-aqueux |
RU2367644C2 (ru) * | 2005-03-03 | 2009-09-20 | Мицуи Кемикалз, Инк. | Способ получения олефинов |
-
2007
- 2007-09-20 FR FR0757691A patent/FR2921363B1/fr not_active Expired - Fee Related
-
2008
- 2008-09-17 EP EP08837762.7A patent/EP2191003B1/fr not_active Not-in-force
- 2008-09-17 CN CN200880116942A patent/CN101868552A/zh active Pending
- 2008-09-17 WO PCT/FR2008/051664 patent/WO2009047444A1/fr active Application Filing
- 2008-09-17 US US12/678,366 patent/US9023626B2/en not_active Expired - Fee Related
- 2008-09-17 BR BRPI0816431-2A2A patent/BRPI0816431A2/pt not_active Application Discontinuation
- 2008-09-17 JP JP2010525401A patent/JP6073044B2/ja not_active Expired - Fee Related
Patent Citations (1)
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US4474882A (en) * | 1980-10-09 | 1984-10-02 | Daicel Chemical Industries, Ltd. | Microbiological process for the preparation of unsaturated dicarboxylic acids |
Non-Patent Citations (4)
Title |
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A.K. CHATTERJEE ET AL.: "Formal vinyl CH activation and allylic oxidation by olefin metathesis", ANGEW. CHEM. INT.ED., vol. 41, no. 17, 2002, pages 3171 - 3174, XP002481692 * |
C.-X. BAI ET AL.: "Lewis-acid assisted cross metathesis of acrylonitrile with functionalized olefins catalyzed by phosphine-free ruthenium carbene complex.", ORG.BIOMOL.CHEM., vol. 3, 2005, pages 4139 - 4142, XP002481691 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002481693, Database accession no. 1780726 * |
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002481694, Database accession no. 1707959 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140235517A1 (en) * | 2011-02-13 | 2014-08-21 | Trent University | Esters for use as a base stock and in lubricant applications |
US9359571B2 (en) * | 2011-02-13 | 2016-06-07 | Trent University | Esters for use as a base stock and in lubricant applications |
WO2014122410A2 (fr) | 2013-02-08 | 2014-08-14 | Arkema France | Synthese conjuguee d'un nitrile- ester/acide et d'un diester/diacide |
US9382189B2 (en) | 2013-02-08 | 2016-07-05 | Arkema France | Synthesis of a branched unsaturated compound by means of cross metathesis |
US9567293B2 (en) | 2013-02-08 | 2017-02-14 | Arkema France | Combined synthesis of a nitrile-ester/acid and of a diester/diacid |
WO2014125223A1 (fr) | 2013-02-15 | 2014-08-21 | Arkema France | Utilisation de mercapto-esters methyliques en tant qu'agents de transfert de chaine |
Also Published As
Publication number | Publication date |
---|---|
FR2921363A1 (fr) | 2009-03-27 |
FR2921363B1 (fr) | 2009-11-06 |
BRPI0816431A2 (pt) | 2014-10-14 |
US20100196973A1 (en) | 2010-08-05 |
US9023626B2 (en) | 2015-05-05 |
EP2191003A1 (fr) | 2010-06-02 |
JP6073044B2 (ja) | 2017-02-01 |
JP2010539225A (ja) | 2010-12-16 |
EP2191003B1 (fr) | 2015-06-03 |
CN101868552A (zh) | 2010-10-20 |
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