FR3080623B1 - Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse - Google Patents

Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse Download PDF

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Publication number
FR3080623B1
FR3080623B1 FR1853708A FR1853708A FR3080623B1 FR 3080623 B1 FR3080623 B1 FR 3080623B1 FR 1853708 A FR1853708 A FR 1853708A FR 1853708 A FR1853708 A FR 1853708A FR 3080623 B1 FR3080623 B1 FR 3080623B1
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France
Prior art keywords
meth
hydrolysis
thermoplastic
depolymerization
recovery
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Active
Application number
FR1853708A
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English (en)
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FR3080623A1 (fr
Inventor
Jean-Luc Dubois
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
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Arkema France SA
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Publication date
Priority to FR1853708A priority Critical patent/FR3080623B1/fr
Application filed by Arkema France SA filed Critical Arkema France SA
Priority to CA3097475A priority patent/CA3097475A1/fr
Priority to PCT/FR2019/050991 priority patent/WO2019207264A1/fr
Priority to US17/049,735 priority patent/US11739192B2/en
Priority to BR112020021672-0A priority patent/BR112020021672A2/pt
Priority to KR1020207033445A priority patent/KR20210005113A/ko
Priority to EP19729579.3A priority patent/EP3784724A1/fr
Publication of FR3080623A1 publication Critical patent/FR3080623A1/fr
Application granted granted Critical
Publication of FR3080623B1 publication Critical patent/FR3080623B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/14—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with steam or water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/04—Acrylic acid; Methacrylic acid
    • 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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/16—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with inorganic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
    • C08J2333/12—Homopolymers or copolymers of methyl methacrylate
    • 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
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Abstract

L'invention porte sur un procédé de recyclage (100) d'un article à base de résine polymère thermoplastique (méth)acrylique, caractérisé en ce qu'il comprend les étapes suivantes : - introduction (110) de l'article dans un système adapté pour le recyclage de polymère thermoplastique, - dépolymérisation (130) au moins partielle de la résine polymère thermoplastique (méth)acrylique de façon à former des monomères (méth)acrylates, - introduction (140) d'un catalyseur d'hydrolyse dans un réacteur d'hydrolyse, - introduction (150) d'eau dans ledit réacteur d'hydrolyse, et - conversion (160) dans le réacteur d'hydrolyse, d'au moins une partie des monomères (méth)acrylates en acide (méth)acrylique. L'invention porte en outre sur un système de recyclage d'un article à base de résine polymère thermoplastique (méth)acrylique.
FR1853708A 2018-04-27 2018-04-27 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse Active FR3080623B1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FR1853708A FR3080623B1 (fr) 2018-04-27 2018-04-27 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse
PCT/FR2019/050991 WO2019207264A1 (fr) 2018-04-27 2019-04-26 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse
US17/049,735 US11739192B2 (en) 2018-04-27 2019-04-26 Recovery of (meth) acrylic resin by depolymerization and hydrolysis
BR112020021672-0A BR112020021672A2 (pt) 2018-04-27 2019-04-26 recuperação de resina (met)acrílica por despolimerização e hidrólise
CA3097475A CA3097475A1 (fr) 2018-04-27 2019-04-26 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse
KR1020207033445A KR20210005113A (ko) 2018-04-27 2019-04-26 해중합 및 가수분해에 의한 (메트)아크릴 수지의 회수
EP19729579.3A EP3784724A1 (fr) 2018-04-27 2019-04-26 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1853708A FR3080623B1 (fr) 2018-04-27 2018-04-27 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse
FR1853708 2018-04-27

Publications (2)

Publication Number Publication Date
FR3080623A1 FR3080623A1 (fr) 2019-11-01
FR3080623B1 true FR3080623B1 (fr) 2021-01-08

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
FR1853708A Active FR3080623B1 (fr) 2018-04-27 2018-04-27 Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse

Country Status (7)

Country Link
US (1) US11739192B2 (fr)
EP (1) EP3784724A1 (fr)
KR (1) KR20210005113A (fr)
BR (1) BR112020021672A2 (fr)
CA (1) CA3097475A1 (fr)
FR (1) FR3080623B1 (fr)
WO (1) WO2019207264A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3117678B1 (fr) 2020-12-16 2024-02-23 Arkema France Article composite à base d’une matrice thermoplastique intégrant au moins un transducteur comprenant un polymère piézoélectrique
CN114634413B (zh) * 2022-04-02 2023-05-26 北京化工大学 一种聚甲基丙烯酸甲酯催化解聚为单体的方法和反应装置
JP2024019097A (ja) * 2022-07-29 2024-02-08 住友化学株式会社 メタクリル酸メチル組成物
EP4321500A1 (fr) * 2022-08-08 2024-02-14 Arkema France Procédé et installation pour la production d'un monomère par dépolymérisation du polymère correspondant

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19729065A1 (de) * 1997-07-08 1999-01-14 Ver Foerderung Inst Kunststoff Verfahren zur Depolymerisation von Polymethylmethacrylat (PMMA) unter Einwirkung von Wärme und unter Verwendung von Zusatzstoffen
FR2781393B1 (fr) * 1998-07-22 2000-08-25 Rhone Poulenc Fibres Procede de regeneration d'un catalyseur d'hydrolyse cyclisante d'un aminonitrile en lactame et utilisation du catalyseur regenere pour la fabrication de lactames
EP1352891A1 (fr) * 2002-04-12 2003-10-15 Oleon Procédé pour l'hydrolyse directe d'esters d'acides gras en acides gras correspondants
JP4022748B2 (ja) 2002-09-18 2007-12-19 富士ゼロックス株式会社 色処理方法および色処理装置、記録媒体、色処理プログラム、画像形成装置
US20080021241A1 (en) * 2004-11-12 2008-01-24 Carlson Curtis I Jr Process for production of methacrylic acid
CN102247705B (zh) * 2011-04-07 2014-04-30 上海通凌新能源科技发展有限公司 蒸馏过程中废热能源再利用的系统及再利用方法
DE102011076642A1 (de) * 2011-05-27 2012-11-29 Evonik Röhm Gmbh Verfahren zur Herstellung von Methacrylsäure
CN103588636A (zh) * 2013-11-14 2014-02-19 中国科学院过程工程研究所 一种以酸性树脂催化丙烯酸甲酯水解制备丙烯酸的方法
EP3144291A1 (fr) * 2015-09-16 2017-03-22 Evonik Röhm GmbH Synthese d'acide methacrylique a partir de methacrylate d'alkyle a base de methacroleine

Also Published As

Publication number Publication date
KR20210005113A (ko) 2021-01-13
US11739192B2 (en) 2023-08-29
WO2019207264A1 (fr) 2019-10-31
US20210040288A1 (en) 2021-02-11
EP3784724A1 (fr) 2021-03-03
CA3097475A1 (fr) 2019-10-31
FR3080623A1 (fr) 2019-11-01
BR112020021672A2 (pt) 2021-01-26

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