WO2008024023A1 - Catalyseur permettant d'obtenir des éthers d'acide acrylique selon une réaction de métathèse de dialkylmaléates (variantes), et composition catalytique associée - Google Patents

Catalyseur permettant d'obtenir des éthers d'acide acrylique selon une réaction de métathèse de dialkylmaléates (variantes), et composition catalytique associée Download PDF

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Publication number
WO2008024023A1
WO2008024023A1 PCT/RU2007/000415 RU2007000415W WO2008024023A1 WO 2008024023 A1 WO2008024023 A1 WO 2008024023A1 RU 2007000415 W RU2007000415 W RU 2007000415W WO 2008024023 A1 WO2008024023 A1 WO 2008024023A1
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WO
WIPO (PCT)
Prior art keywords
catalyst
reaction
ethylene
acrylic acid
isopropoxystyrene
Prior art date
Application number
PCT/RU2007/000415
Other languages
English (en)
Russian (ru)
Inventor
Aleksei Vadimovich Nizovtsev
Egor Vladimirovich Shutko
Vladimir Vladimirovich Afanasiev
Tatyana Modestovna Dolgina
Natalya Borisovna Bespalova
Original Assignee
Limited Liability Company 'united Research And Development Centre'
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Filing date
Publication date
Application filed by Limited Liability Company 'united Research And Development Centre' filed Critical Limited Liability Company 'united Research And Development Centre'
Publication of WO2008024023A1 publication Critical patent/WO2008024023A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2269—Heterocyclic carbenes
    • B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4092—Regeneration or reactivation of catalysts containing metals involving a stripping step, with stripping gas or solvent
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • 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

La présente invention relève de la synthèse organique et se rapporte en particulier à la production d'un catalyseur homogène permettant d'obtenir des éthers d'acide acrylique selon une réaction de métathèse de maléates avec de l'éthylène. L'invention concerne deux variantes de catalyseur permettant d'obtenir des éthers d'acide acrylique selon une réaction de métathèse de dialkylmaléates avec de l'éthylène, à savoir un catalyseur de formule (I) et un catalyseur de formule (II). L'utilisation des catalyseurs selon l'invention permet d'augmenter le nombre de cycles de ces derniers au cours de la métathèse de dialkylmaléates avec de l'éthylène, aussi bien à des températures modérées (proches de 50 °C) lors d'un processus sans stripping du produit, qu'à des températures proches de 120 °C lorsque l'acrylate obtenu est strippé du mélange réactionnel. L'invention concerne également une composition catalytique qui permet d'augmenter non seulement le nombre de cycles mais également la durée de vie du catalyseur, et qui est particulièrement efficace à des températures proches de 120 °C, lorsque l'acrylate formé est strippé du mélange réactionnel. Une telle composition contient ledit catalyseur et du 2-isopropoxystyrol ou des dérivés de ce dernier, en un rapport correspondant à 1 équivalent molaire de catalyseur pour 5 à 100 équivalents molaires de 2-isopropoxystyrol ou de son dérivé.
PCT/RU2007/000415 2006-08-15 2007-07-30 Catalyseur permettant d'obtenir des éthers d'acide acrylique selon une réaction de métathèse de dialkylmaléates (variantes), et composition catalytique associée WO2008024023A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2006129578/04A RU2311231C1 (ru) 2006-08-15 2006-08-15 Катализатор для получения эфиров акриловой кислоты по реакции метатезиса диалкилмалеатов (варианты) и каталитическая композиция на его основе
RU2006129578 2006-08-15

Publications (1)

Publication Number Publication Date
WO2008024023A1 true WO2008024023A1 (fr) 2008-02-28

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PCT/RU2007/000415 WO2008024023A1 (fr) 2006-08-15 2007-07-30 Catalyseur permettant d'obtenir des éthers d'acide acrylique selon une réaction de métathèse de dialkylmaléates (variantes), et composition catalytique associée

Country Status (2)

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RU (1) RU2311231C1 (fr)
WO (1) WO2008024023A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009045637A2 (fr) * 2007-08-10 2009-04-09 Genomatica, Inc. Procédés de synthèse d'oléfines et de dérivés
EP2269974A1 (fr) * 2009-07-02 2011-01-05 Stichting Dienst Landbouwkundig Onderzoek Synthèse d'oléfines d'origine biologique
JP2011523625A (ja) * 2008-04-09 2011-08-18 マテリア， インコーポレイテッド 置換された骨格を有するｎ−ヘテロ環状カルベンリガンドを有するルテニウムオレフィン複分解触媒
US8691553B2 (en) 2008-01-22 2014-04-08 Genomatica, Inc. Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol
US8865439B2 (en) 2008-05-01 2014-10-21 Genomatica, Inc. Microorganisms for the production of methacrylic acid
US8993285B2 (en) 2009-04-30 2015-03-31 Genomatica, Inc. Organisms for the production of isopropanol, n-butanol, and isobutanol
US9017983B2 (en) 2009-04-30 2015-04-28 Genomatica, Inc. Organisms for the production of 1,3-butanediol
US9023636B2 (en) 2010-04-30 2015-05-05 Genomatica, Inc. Microorganisms and methods for the biosynthesis of propylene
US9260729B2 (en) 2008-03-05 2016-02-16 Genomatica, Inc. Primary alcohol producing organisms
US9562241B2 (en) 2009-08-05 2017-02-07 Genomatica, Inc. Semi-synthetic terephthalic acid via microorganisms that produce muconic acid
US10167477B2 (en) 2009-10-23 2019-01-01 Genomatica, Inc. Microorganisms and methods for the production of aniline
US10385344B2 (en) 2010-01-29 2019-08-20 Genomatica, Inc. Microorganisms and methods for the biosynthesis of (2-hydroxy-3methyl-4-oxobutoxy) phosphonate
US10793882B2 (en) 2010-07-26 2020-10-06 Genomatica, Inc. Microorganisms and methods for the biosynthesis of aromatics, 2,4-pentadienoate and 1,3-butadiene

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WO2011079439A1 (fr) * 2009-12-30 2011-07-07 Zannan Scitech Co., Ltd. Catalyseurs de métathèse d'activité élevée sélectifs vis-à-vis des réactions de romp et de rcm
PL400162A1 (pl) * 2012-07-27 2014-02-03 Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy

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WO2004035596A1 (fr) * 2002-10-15 2004-04-29 Boehringer Ingelheim International Gmbh Complexes de ruthenium en tant que (pre)catalyseurs de reaction de metathese
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Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2543657A3 (fr) * 2007-08-10 2013-08-14 Genomatica, Inc. Procédés pour la synthèse d'acide acrylique et dérivés à partir de l'acide fumarique
WO2009045637A3 (fr) * 2007-08-10 2009-09-03 Genomatica, Inc. Procédés de synthèse d'oléfines et de dérivés
US10081587B2 (en) 2007-08-10 2018-09-25 Genomatica, Inc. Methods for the synthesis of olefins and derivatives
US9365874B2 (en) 2007-08-10 2016-06-14 Genomatica, Inc. Methods for synthesis of olefins and derivatives
EP2348008A1 (fr) * 2007-08-10 2011-07-27 Genomatica, Inc. Procédés pour la synthèse d'acide acrylique et dérivés à partir d'acide fumarique
WO2009045637A2 (fr) * 2007-08-10 2009-04-09 Genomatica, Inc. Procédés de synthèse d'oléfines et de dérivés
US8455683B2 (en) 2007-08-10 2013-06-04 Genomatica, Inc. Methods for the synthesis of olefins and derivatives
US9051552B2 (en) 2008-01-22 2015-06-09 Genomatica, Inc. Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol
US8691553B2 (en) 2008-01-22 2014-04-08 Genomatica, Inc. Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol
US11613767B2 (en) 2008-03-05 2023-03-28 Genomatica, Inc. Primary alcohol producing organisms
US9260729B2 (en) 2008-03-05 2016-02-16 Genomatica, Inc. Primary alcohol producing organisms
US10208320B2 (en) 2008-03-05 2019-02-19 Genomatica, Inc. Primary alcohol producing organisms
JP2011523625A (ja) * 2008-04-09 2011-08-18 マテリア， インコーポレイテッド 置換された骨格を有するｎ−ヘテロ環状カルベンリガンドを有するルテニウムオレフィン複分解触媒
US9951355B2 (en) 2008-05-01 2018-04-24 Genomatica, Inc. Microorganisms for the production of methacrylic acid
US8865439B2 (en) 2008-05-01 2014-10-21 Genomatica, Inc. Microorganisms for the production of methacrylic acid
US8900837B2 (en) 2008-05-01 2014-12-02 Genomatica, Inc. Microorganisms for the production of 2-hydroxyisobutyric acid
US8993285B2 (en) 2009-04-30 2015-03-31 Genomatica, Inc. Organisms for the production of isopropanol, n-butanol, and isobutanol
US9017983B2 (en) 2009-04-30 2015-04-28 Genomatica, Inc. Organisms for the production of 1,3-butanediol
WO2011002284A1 (fr) * 2009-07-02 2011-01-06 Stichting Dienst Landbouwkundig Onderzoek Synthèse d'oléfines d'origine biologique
EP2269974A1 (fr) * 2009-07-02 2011-01-05 Stichting Dienst Landbouwkundig Onderzoek Synthèse d'oléfines d'origine biologique
US10041093B2 (en) 2009-08-05 2018-08-07 Genomatica, Inc. Semi-synthetic terephthalic acid via microorganisms that produce muconic acid
US9562241B2 (en) 2009-08-05 2017-02-07 Genomatica, Inc. Semi-synthetic terephthalic acid via microorganisms that produce muconic acid
US10415063B2 (en) 2009-08-05 2019-09-17 Genomatica, Inc. Semi-synthetic terephthalic acid via microorganisms that produce muconic acid
US10167477B2 (en) 2009-10-23 2019-01-01 Genomatica, Inc. Microorganisms and methods for the production of aniline
US10612029B2 (en) 2009-10-23 2020-04-07 Genomatica, Inc. Microorganisms and methods for the production of aniline
US10385344B2 (en) 2010-01-29 2019-08-20 Genomatica, Inc. Microorganisms and methods for the biosynthesis of (2-hydroxy-3methyl-4-oxobutoxy) phosphonate
US9023636B2 (en) 2010-04-30 2015-05-05 Genomatica, Inc. Microorganisms and methods for the biosynthesis of propylene
US10793882B2 (en) 2010-07-26 2020-10-06 Genomatica, Inc. Microorganisms and methods for the biosynthesis of aromatics, 2,4-pentadienoate and 1,3-butadiene

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Publication number Publication date
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