JP2010539225A5 - - Google Patents
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- JP2010539225A5 JP2010539225A5 JP2010525401A JP2010525401A JP2010539225A5 JP 2010539225 A5 JP2010539225 A5 JP 2010539225A5 JP 2010525401 A JP2010525401 A JP 2010525401A JP 2010525401 A JP2010525401 A JP 2010525401A JP 2010539225 A5 JP2010539225 A5 JP 2010539225A5
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- JP
- Japan
- Prior art keywords
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- acid
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- carbon atoms
- formula
- Prior art date
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- 150000005690 diesters Chemical class 0.000 claims description 5
- 238000005686 cross metathesis reaction Methods 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- JHVMNDBTBXOUQL-UHFFFAOYSA-N pentadec-2-enedioic acid Chemical compound OC(=O)CCCCCCCCCCCC=CC(O)=O JHVMNDBTBXOUQL-UHFFFAOYSA-N 0.000 claims description 2
- PRHYKPOPIDLQKJ-UHFFFAOYSA-N undec-2-enedioic acid Chemical compound OC(=O)CCCCCCCC=CC(O)=O PRHYKPOPIDLQKJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 102000004020 Oxygenases Human genes 0.000 claims 2
- 108090000417 Oxygenases Proteins 0.000 claims 2
- 238000000855 fermentation Methods 0.000 claims 2
- 230000004151 fermentation Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims 1
- 241000222178 Candida tropicalis Species 0.000 claims 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- 238000005649 metathesis reaction Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UHODXFUBERXNHW-UHFFFAOYSA-N docos-9-enedioic acid Chemical compound OC(=O)CCCCCCCCCCCC=CCCCCCCCC(O)=O UHODXFUBERXNHW-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- ZRPFJAPZDXQHSM-UHFFFAOYSA-L 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole;dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)CCN1C1=C(C)C=C(C)C=C1C ZRPFJAPZDXQHSM-UHFFFAOYSA-L 0.000 description 1
- AQBHDSSFDBDOLS-UHFFFAOYSA-N 11-methoxy-11-oxoundec-9-enoic acid Chemical compound COC(=O)C=CCCCCCCCC(O)=O AQBHDSSFDBDOLS-UHFFFAOYSA-N 0.000 description 1
- GRZDROOKRHIWCK-UHFFFAOYSA-N 18-methoxy-18-oxooctadec-9-enoic acid Chemical compound COC(=O)CCCCCCCC=CCCCCCCCC(O)=O GRZDROOKRHIWCK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HVJJUDAMOHYMRL-UHFFFAOYSA-L dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)Cl HVJJUDAMOHYMRL-UHFFFAOYSA-L 0.000 description 1
- AASUFOVSZUIILF-UHFFFAOYSA-N diphenylmethanone;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AASUFOVSZUIILF-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0757691 | 2007-09-20 | ||
| 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 |
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010539225A JP2010539225A (ja) | 2010-12-16 |
| JP2010539225A5 true JP2010539225A5 (enExample) | 2016-09-01 |
| JP6073044B2 JP6073044B2 (ja) | 2017-02-01 |
Family
ID=39401187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525401A Expired - Fee Related 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 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9023626B2 (enExample) |
| EP (1) | EP2191003B1 (enExample) |
| JP (1) | JP6073044B2 (enExample) |
| CN (1) | CN101868552A (enExample) |
| BR (1) | BRPI0816431A2 (enExample) |
| FR (1) | FR2921363B1 (enExample) |
| WO (1) | WO2009047444A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010081885A2 (en) * | 2009-01-15 | 2010-07-22 | Basf Se | Method for the production of glutaconate |
| DE102010010984A1 (de) * | 2010-03-10 | 2011-09-15 | Emery Oleochemicals Gmbh | Verfahren zur Herstellung von Dicarbonsäuren oder Dicarbonsäureestern durch Metathese |
| WO2012071439A1 (en) * | 2010-11-22 | 2012-05-31 | The Regents Of The University Of California | Host cells and methods for producing diacid compounds |
| US8741822B2 (en) * | 2011-02-13 | 2014-06-03 | Trent University | Esters for use as a base stock and in lubricant applications |
| 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 |
| US20140171677A1 (en) | 2012-11-30 | 2014-06-19 | Elevance Renewable Sciences, Inc. | Methods of Making Functionalized Internal Olefins and Uses Thereof |
| FR3001966A1 (fr) | 2013-02-08 | 2014-08-15 | Arkema France | Synthese conjuguee d'un nitrile- ester/acide et d'un diester/diacide |
| FR3001964B1 (fr) | 2013-02-08 | 2015-02-20 | Arkema France | Synthese de compose insature ramifie par metathese croisee |
| FR3002230B1 (fr) | 2013-02-15 | 2016-02-05 | Arkema France | Utilisation de mercapto-esters methyliques en tant qu'agents de transfert de chaine |
| 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 |
| FI128953B (en) * | 2019-09-26 | 2021-03-31 | Neste Oyj | Production of renewable chemicals including metathesis and microbial oxidation |
| US20230089404A1 (en) * | 2021-09-18 | 2023-03-23 | Indian Oil Corporation Limited | Bioassisted Process For Selective Conversion Of Alkane Rich Refinery Stream |
| IT202200026568A1 (it) | 2022-12-22 | 2024-06-22 | Novamont Spa | Produzione fermentativa di acidi dicarbossilici |
| JP7716790B1 (ja) * | 2024-05-24 | 2025-08-01 | 築野グループ株式会社 | 水素化不飽和二塩基酸組成物、水素化不飽和二塩基酸組成物の製造方法、ポリエステル組成物、及びポリアミド組成物 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (enExample) * | 1972-06-28 | 1980-11-07 | ||
| JPS5592691A (en) | 1978-12-28 | 1980-07-14 | Baiorisaac Center:Kk | Purification of dicarboxylic acid produced by fermentation |
| JPS5765194A (en) * | 1980-10-09 | 1982-04-20 | Daicel Chem Ind Ltd | Microbial preparation of unsaturated dicarboxylic acid |
| US5254466A (en) | 1989-11-06 | 1993-10-19 | Henkel Research Corporation | Site-specific modification of the candida tropicals genome |
| WO2000043343A2 (en) * | 1999-01-26 | 2000-07-27 | California Institute Of Technology | Novel methods for cross-metathesis of terminal olefins |
| DE19907519A1 (de) * | 1999-02-22 | 2000-08-31 | Basf Ag | Verfahren zur Herstellung von substituierten Olefinen |
| CN1213032C (zh) * | 1999-05-24 | 2005-08-03 | 加州理工学院 | 咪唑烷基金属卡宾易位催化剂 |
| DE59905469D1 (de) * | 1999-08-05 | 2003-06-12 | 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 |
| JP4943612B2 (ja) * | 1999-11-18 | 2012-05-30 | エル ペダーソン リチャード | フェロモン又はその成分のメタセシス合成方法 |
| 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 US US12/678,366 patent/US9023626B2/en not_active Expired - Fee Related
- 2008-09-17 JP JP2010525401A patent/JP6073044B2/ja not_active Expired - Fee Related
- 2008-09-17 CN CN200880116942A patent/CN101868552A/zh active Pending
- 2008-09-17 BR BRPI0816431-2A2A patent/BRPI0816431A2/pt not_active Application Discontinuation
- 2008-09-17 WO PCT/FR2008/051664 patent/WO2009047444A1/fr not_active Ceased
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