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WO2010010309A3 - Procede de synthese d'esters de l'acide acrylique bioressources - Google Patents

Procede de synthese d'esters de l'acide acrylique bioressources Download PDF

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Publication number
WO2010010309A3
WO2010010309A3 PCT/FR2009/051491 FR2009051491W WO2010010309A3 WO 2010010309 A3 WO2010010309 A3 WO 2010010309A3 FR 2009051491 W FR2009051491 W FR 2009051491W WO 2010010309 A3 WO2010010309 A3 WO 2010010309A3
Authority
WO
WIPO (PCT)
Prior art keywords
acrylic acid
synthesis
acid esters
bioresourced
subjected
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/FR2009/051491
Other languages
English (en)
Other versions
WO2010010309A2 (fr
Inventor
Jean-Luc Dubois
Alain Riondel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Arkema France SA
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
Priority to US13/055,864 priority Critical patent/US20110190464A1/en
Priority to RU2011106917/04A priority patent/RU2514422C2/ru
Priority to BRPI0911712A priority patent/BRPI0911712A2/pt
Priority to CN200980137294XA priority patent/CN102164885A/zh
Priority to JP2011519223A priority patent/JP2011529034A/ja
Priority to KR1020137023517A priority patent/KR101441268B1/ko
Application filed by Arkema France SA filed Critical Arkema France SA
Priority to EP09740377A priority patent/EP2321253A2/fr
Publication of WO2010010309A2 publication Critical patent/WO2010010309A2/fr
Publication of WO2010010309A3 publication Critical patent/WO2010010309A3/fr
Priority to ZA2011/00528A priority patent/ZA201100528B/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/52Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C07C51/252Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/03Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/08Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54Acrylic acid esters; Methacrylic acid esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10Esters
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/582Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L'invention vise un procédé de synthèse d'un ester de l'acide acrylique de formule CH2=CH-COO-R dans laquelle R représente un radical alkyle comportant de 1 à 18 atomes de carbone et comprenant le cas échéant un hétéroatome, l'azote, caractérisé en ce que dans une première étape on soumet du glycérol CH2OH-CHOH- CH2OH à une réaction de déshydratation en présence d'un catalyseur acide pour obtenir de l'acroléine de formule CH2=CH-CHO, puis, dans une deuxième étape on transforme l'acroléine ainsi formée par oxydation catalytique en acide acrylique CH2=CH-COOH puis, dans une troisième étape, on soumet l'acide issu de la deuxième étape à une réaction d'estérifîcation au moyen d'un alcool ROH dans lequel R a la signification donnée ci-dessus. L'invention vise également les esters bioressourcés fabriqués selon le procédé ainsi que les polymères synthétisés en utilisant ces esters comme monomères ou comonomères de polymérisation.
PCT/FR2009/051491 2008-07-25 2009-07-24 Procede de synthese d'esters de l'acide acrylique bioressources Ceased WO2010010309A2 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
RU2011106917/04A RU2514422C2 (ru) 2008-07-25 2009-07-24 Способ синтеза биоресурсных сложных эфиров акриловой кислоты
BRPI0911712A BRPI0911712A2 (pt) 2008-07-25 2009-07-24 processo de síntese de um éter do ácido acrílico, ésteres, processo de síntese de um aminoester do ácido acrílico, aminoéster do ácido acrílico, uso dos ésteres e polímeros ou copolímeros "
CN200980137294XA CN102164885A (zh) 2008-07-25 2009-07-24 用于合成生物来源化的丙烯酸酯的方法
JP2011519223A JP2011529034A (ja) 2008-07-25 2009-07-24 生物材料を起源とするアクリル酸エステルの合成方法
KR1020137023517A KR101441268B1 (ko) 2008-07-25 2009-07-24 생물자원화 아크릴산 에스테르의 합성 방법
US13/055,864 US20110190464A1 (en) 2008-07-25 2009-07-24 Method for the synthesis of bioresourced acrylic acid esters
EP09740377A EP2321253A2 (fr) 2008-07-25 2009-07-24 Procede de synthese d'esters de l'acide acrylique bioressources
ZA2011/00528A ZA201100528B (en) 2008-07-25 2011-01-20 Method for the synthesis of bioresourced acrylic acid esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0855125A FR2934261B1 (fr) 2008-07-25 2008-07-25 Procede de synthese d'esters de l'acide acrylique
FR0855125 2008-07-25

Publications (2)

Publication Number Publication Date
WO2010010309A2 WO2010010309A2 (fr) 2010-01-28
WO2010010309A3 true WO2010010309A3 (fr) 2010-03-18

Family

ID=40527595

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2009/051491 Ceased WO2010010309A2 (fr) 2008-07-25 2009-07-24 Procede de synthese d'esters de l'acide acrylique bioressources

Country Status (11)

Country Link
US (1) US20110190464A1 (fr)
EP (1) EP2321253A2 (fr)
JP (2) JP2011529034A (fr)
KR (2) KR101441268B1 (fr)
CN (1) CN102164885A (fr)
BR (1) BRPI0911712A2 (fr)
FR (1) FR2934261B1 (fr)
MY (1) MY157134A (fr)
RU (1) RU2514422C2 (fr)
WO (1) WO2010010309A2 (fr)
ZA (1) ZA201100528B (fr)

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JP2011168502A (ja) * 2010-02-16 2011-09-01 Teijin Ltd 芳香族カルボン酸化合物
JP2011168501A (ja) * 2010-02-16 2011-09-01 Teijin Ltd 芳香族カルボン酸エステル化合物
BR112013004935A2 (pt) * 2010-09-07 2016-08-02 Myriant Corp "desitratação catalítica de ácido láctico e ésteres de ácido láctico".
FR2968659B1 (fr) * 2010-12-08 2013-04-26 Arkema France Procede de preparation de (meth)acrylates d'alkylaminoalkyle
DE102011081649A1 (de) 2011-08-26 2013-02-28 Evonik Röhm Gmbh Längerkettige Methacrylate aus nachwachsenden Rohstoffen
FR2985998B1 (fr) * 2012-01-23 2014-01-31 Arkema France Procede de production d'acrylate de 2-octyle par transesterification
FR2985999B1 (fr) * 2012-01-23 2014-01-31 Arkema France Procede de production d'acrylate de 2-octyle par transesterification
CN104837799B (zh) * 2012-12-07 2020-07-31 艾菲纽技术公司 将可自生物质衍生得的脂肪醇催化转化制得有价值的烯烃或含氧化合物
KR101616528B1 (ko) * 2013-07-16 2016-04-28 주식회사 엘지화학 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법
FR3008971B1 (fr) * 2013-07-29 2016-08-19 Arkema France Procede de production en continu d'acrylates legers par esterification d'un acide acrylique de grade ester brut
CA2861524A1 (fr) 2013-09-16 2014-11-03 Armstrong World Industries, Inc. Procedes de preparation d'acide methacrylique a partir de materiaux d'origine biologique
KR101606191B1 (ko) 2013-09-30 2016-03-24 주식회사 엘지화학 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법
PT3194357T (pt) 2014-09-19 2019-07-25 Sibur Holding Public Joint Stock Co Processo para a preparação de ésteres de ácido carboxílico na presença de um catalisador contendo titânio
KR101774543B1 (ko) 2014-12-19 2017-09-04 주식회사 엘지화학 글리세린 탈수 반응용 촉매, 이의 제조 방법 및 상기 촉매를 이용한 아크롤레인의 제조 방법
CN110586120A (zh) * 2018-06-12 2019-12-20 中国石油化工股份有限公司 负载型丙烯酸催化剂合成丙烯酸的方法
EP3862815A4 (fr) * 2018-10-03 2021-11-03 FUJIFILM Corporation Solution chimique, réceptacle de solution chimique, procédé de formation de motif de réserve, et procédé de fabrication de puce à semi-conducteur
KR102371579B1 (ko) 2019-05-09 2022-03-07 주식회사 엘지화학 (메트)아크릴산 에스테르계 화합물 제조방법
BR102020022314A2 (pt) * 2020-10-30 2022-05-10 Oxiteno S.A. Indústria E Comércio Processo para a preparação de poliacrilatos alcoxilados funcionais, poliacrilatos alcoxilados funcionais, e, uso dos mesmos
CN119958945B (zh) * 2025-04-07 2025-09-02 恩德斯豪斯(北京)科技有限公司 一种生物源碳同位素富集方法及系统

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US2917538A (en) * 1957-12-19 1959-12-15 Dow Chemical Co Process for the production of acrylic acid esters
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Also Published As

Publication number Publication date
KR20110022704A (ko) 2011-03-07
MY157134A (en) 2016-05-13
US20110190464A1 (en) 2011-08-04
JP2011529034A (ja) 2011-12-01
CN102164885A (zh) 2011-08-24
RU2514422C2 (ru) 2014-04-27
RU2011106917A (ru) 2012-08-27
FR2934261B1 (fr) 2015-04-10
JP2014205668A (ja) 2014-10-30
KR101441268B1 (ko) 2014-09-17
ZA201100528B (en) 2012-05-01
BRPI0911712A2 (pt) 2015-10-06
KR20130103639A (ko) 2013-09-23
FR2934261A1 (fr) 2010-01-29
EP2321253A2 (fr) 2011-05-18
WO2010010309A2 (fr) 2010-01-28

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