DE102012002282A1 - Verfahren zur Herstellung von Vinylestern - Google Patents

Verfahren zur Herstellung von Vinylestern Download PDF

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Publication number
DE102012002282A1
DE102012002282A1 DE102012002282A DE102012002282A DE102012002282A1 DE 102012002282 A1 DE102012002282 A1 DE 102012002282A1 DE 102012002282 A DE102012002282 A DE 102012002282A DE 102012002282 A DE102012002282 A DE 102012002282A DE 102012002282 A1 DE102012002282 A1 DE 102012002282A1
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DE
Germany
Prior art keywords
acid
reaction
transition metal
transvinylation
carboxylic acid
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
DE102012002282A
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German (de)
English (en)
Inventor
Leif Johnen
Heinz Strutz
Kurt Schalapski
Dr. Nowotny Norman
Wolfgang Höfs
Sebastian Geisel
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.)
Oxea GmbH
Original Assignee
OQ Chemicals GmbH
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
Application filed by OQ Chemicals GmbH filed Critical OQ Chemicals GmbH
Priority to DE102012002282A priority Critical patent/DE102012002282A1/de
Priority to BR112014019187A priority patent/BR112014019187B1/pt
Priority to US14/372,290 priority patent/US9174922B2/en
Priority to EP13701905.5A priority patent/EP2812307B1/de
Priority to KR1020147021631A priority patent/KR101988210B1/ko
Priority to HK15103748.2A priority patent/HK1203189A1/xx
Priority to JP2014555116A priority patent/JP6041904B2/ja
Priority to IN1079KON2014 priority patent/IN2014KN01079A/en
Priority to CN201380007000.8A priority patent/CN104487411A/zh
Priority to ES13701905.5T priority patent/ES2669520T3/es
Priority to PCT/EP2013/000141 priority patent/WO2013117294A1/de
Priority to PL13701905T priority patent/PL2812307T3/pl
Priority to TW102104105A priority patent/TWI461400B/zh
Publication of DE102012002282A1 publication Critical patent/DE102012002282A1/de
Ceased legal-status Critical Current

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    • 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
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C07C69/01—Vinyl esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
DE102012002282A 2012-02-06 2012-02-06 Verfahren zur Herstellung von Vinylestern Ceased DE102012002282A1 (de)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DE102012002282A DE102012002282A1 (de) 2012-02-06 2012-02-06 Verfahren zur Herstellung von Vinylestern
BR112014019187A BR112014019187B1 (pt) 2012-02-06 2013-01-18 processo para a produção de ésteres vinílicos
US14/372,290 US9174922B2 (en) 2012-02-06 2013-01-18 Method for producing vinyl esters
EP13701905.5A EP2812307B1 (de) 2012-02-06 2013-01-18 Verfahren zur herstellung von vinylestern
KR1020147021631A KR101988210B1 (ko) 2012-02-06 2013-01-18 비닐 에스테르의 제조 방법
HK15103748.2A HK1203189A1 (en) 2012-02-06 2013-01-18 Method for producing vinyl esters
JP2014555116A JP6041904B2 (ja) 2012-02-06 2013-01-18 ビニルエステルの製造方法
IN1079KON2014 IN2014KN01079A (enExample) 2012-02-06 2013-01-18
CN201380007000.8A CN104487411A (zh) 2012-02-06 2013-01-18 生产乙烯酯的方法
ES13701905.5T ES2669520T3 (es) 2012-02-06 2013-01-18 Método para la producción de ésteres vinílicos
PCT/EP2013/000141 WO2013117294A1 (de) 2012-02-06 2013-01-18 Verfahren zur herstellung von vinylestern
PL13701905T PL2812307T3 (pl) 2012-02-06 2013-01-18 Sposób wytwarzania estrów winylowych
TW102104105A TWI461400B (zh) 2012-02-06 2013-02-04 乙烯酯之連續催化製法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102012002282A DE102012002282A1 (de) 2012-02-06 2012-02-06 Verfahren zur Herstellung von Vinylestern

Publications (1)

Publication Number Publication Date
DE102012002282A1 true DE102012002282A1 (de) 2013-08-08

Family

ID=47630236

Family Applications (1)

Application Number Title Priority Date Filing Date
DE102012002282A Ceased DE102012002282A1 (de) 2012-02-06 2012-02-06 Verfahren zur Herstellung von Vinylestern

Country Status (13)

Country Link
US (1) US9174922B2 (enExample)
EP (1) EP2812307B1 (enExample)
JP (1) JP6041904B2 (enExample)
KR (1) KR101988210B1 (enExample)
CN (1) CN104487411A (enExample)
BR (1) BR112014019187B1 (enExample)
DE (1) DE102012002282A1 (enExample)
ES (1) ES2669520T3 (enExample)
HK (1) HK1203189A1 (enExample)
IN (1) IN2014KN01079A (enExample)
PL (1) PL2812307T3 (enExample)
TW (1) TWI461400B (enExample)
WO (1) WO2013117294A1 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012105879A1 (de) 2012-07-02 2014-01-02 Oxea Gmbh Verfahren zur Herstellung von Isononylderivaten
DE102012105874A1 (de) 2012-07-02 2014-01-02 Oxea Gmbh Verfahren zur Herstellung von Isononansäurevinylestern
DE102012014396A1 (de) 2012-07-13 2014-01-16 Oxea Gmbh Vinylester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu seiner Herstellung sowie seine Verwendung
DE102014013123A1 (de) 2014-08-30 2016-03-03 Oxea Gmbh Verfahren zur Herstellung von Gemischen enthaltend tertiäre lsononansäuren ausgehend von 2-Ethylhexanol

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013224496A1 (de) 2013-11-29 2015-06-03 Wacker Chemie Ag Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102013224491A1 (de) 2013-11-29 2015-06-03 Wacker Chemie Ag Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102014206915A1 (de) 2014-04-10 2015-10-15 Wacker Chemie Ag Verfahren zur Darstellung einer aktiven Ruthenium-Katalysatorlösung für die Umvinylierung von Carbonsäuren
DE102014206916A1 (de) * 2014-04-10 2015-10-15 Wacker Chemie Ag Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102014210835A1 (de) 2014-06-06 2015-12-17 Wacker Chemie Ag Verfahren zur Trennung von hochsiedenden Carbonsäurevinylester/Carbonsäure-Gemischen
EP3103786A1 (en) * 2015-06-08 2016-12-14 Hexion Research Belgium SA Process for the production of higher carboxylic acid vinyl esters
DE102015216373A1 (de) 2015-08-27 2017-03-02 Wacker Chemie Ag Verfahren zur katalytischen Umvinylierung von Carbonsäuren
CN108057459B (zh) * 2016-11-09 2019-09-20 中国科学院福建物质结构研究所 一种乙烯基交换反应用硅胶负载配位钯催化剂及其制备方法和应用

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2245131A (en) 1941-06-10 Process of preparing vinyl esters
US2299862A (en) 1942-10-27 Preparation of vinyl esters
DE1222493B (de) 1962-04-25 1966-08-11 Rohm & Haas Verfahren zur Herstellung von Vinylestern
EP0351603A2 (en) 1988-06-30 1990-01-24 Union Carbide Corporation Transvinylation reaction
EP0376075A2 (en) 1988-12-26 1990-07-04 Shin-Etsu Vinyl Acetate Co., Ltd. Method for the preparation of an alkenyl carboxylate
EP0497340A2 (en) 1991-01-31 1992-08-05 Union Carbide Chemicals & Plastics Technology Corporation Transvinylation process by reactive distillation
EP0506070A2 (en) 1991-03-28 1992-09-30 Union Carbide Chemicals & Plastics Technology Corporation Transvinylation process for the preparation of thermally labile vinyl compounds and vinyl compounds prepared from thermally labile acids
US5214172A (en) 1991-05-06 1993-05-25 Air Products And Chemicals, Inc. Catalytic transvinylation of vinyl esters
US5223621A (en) 1991-01-04 1993-06-29 Societe Francaise Hoechst Transvinylation of carboxylic acids
US5741925A (en) 1997-01-13 1998-04-21 Air Products And Chemicals, Inc. Transvinylation of naphthenic acids
EP1057525A2 (de) 1999-06-02 2000-12-06 Oxeno Olefinchemie GmbH Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Vinylierungen von Carbonsäuren
JP2002322125A (ja) 2001-04-26 2002-11-08 Japan Vam & Poval Co Ltd カルボン酸ビニルエステルの製造方法
US20040147757A1 (en) * 2002-08-30 2004-07-29 Mitsubishi Chemical Corporation Method for producing allyl compound, and ether or ester compound produced thereby
WO2011139361A1 (en) 2010-05-04 2011-11-10 Celanese International Corporation Process for the semi-continuous transvinylation of carboxylic acids with vinyl acetate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2997495A (en) * 1956-08-27 1961-08-22 Air Reduction Preparation of vinyl esters
DE2823660A1 (de) * 1977-10-13 1979-04-26 Shin Etsu Vinyl Acetate Co Verfahren zur herstellung eines alkenylesters von carbonsaeuren
DE3047347A1 (de) * 1980-12-16 1982-07-22 Wacker-Chemie GmbH, 8000 München Palladium(ii)-katalysator, seine herstellung und verwendung
ECSP910793A (es) * 1990-11-30 1992-12-21 Union Carbide Chem Plastics Co Inc La tecnologia de transvinilacion ayudada azeotropica

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2245131A (en) 1941-06-10 Process of preparing vinyl esters
US2299862A (en) 1942-10-27 Preparation of vinyl esters
DE1222493B (de) 1962-04-25 1966-08-11 Rohm & Haas Verfahren zur Herstellung von Vinylestern
EP0351603A2 (en) 1988-06-30 1990-01-24 Union Carbide Corporation Transvinylation reaction
EP0376075A2 (en) 1988-12-26 1990-07-04 Shin-Etsu Vinyl Acetate Co., Ltd. Method for the preparation of an alkenyl carboxylate
DE68916396T2 (de) * 1988-12-26 1994-10-13 Shin Etsu Vinyl Acetate Co Verfahren zur Herstellung eines Carbonsäurealkenylesters.
US5223621A (en) 1991-01-04 1993-06-29 Societe Francaise Hoechst Transvinylation of carboxylic acids
EP0497340A2 (en) 1991-01-31 1992-08-05 Union Carbide Chemicals & Plastics Technology Corporation Transvinylation process by reactive distillation
EP0506070A2 (en) 1991-03-28 1992-09-30 Union Carbide Chemicals & Plastics Technology Corporation Transvinylation process for the preparation of thermally labile vinyl compounds and vinyl compounds prepared from thermally labile acids
US5214172A (en) 1991-05-06 1993-05-25 Air Products And Chemicals, Inc. Catalytic transvinylation of vinyl esters
US5741925A (en) 1997-01-13 1998-04-21 Air Products And Chemicals, Inc. Transvinylation of naphthenic acids
EP1057525A2 (de) 1999-06-02 2000-12-06 Oxeno Olefinchemie GmbH Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Vinylierungen von Carbonsäuren
JP2002322125A (ja) 2001-04-26 2002-11-08 Japan Vam & Poval Co Ltd カルボン酸ビニルエステルの製造方法
US20040147757A1 (en) * 2002-08-30 2004-07-29 Mitsubishi Chemical Corporation Method for producing allyl compound, and ether or ester compound produced thereby
WO2011139361A1 (en) 2010-05-04 2011-11-10 Celanese International Corporation Process for the semi-continuous transvinylation of carboxylic acids with vinyl acetate
WO2011139360A1 (en) 2010-05-04 2011-11-10 Celanese International Corporation Process for the continuous transvinylation of carboxylic acids with vinyl acetate

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Adelman, Journal Organic Chemistry, 1949, 14, Seiten 1057-1077
G. Hübner, Fette, Seifen, Anstrichmittel 68, 290 (1966), Ullmanns Encyklopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie, Band 23, Seiten 606-607
Ullmanns Encyklopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie, Band 23, Seiten 606- 607
Ullmanns Encyklopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie, Band 9, Seiten 143-145; Band 23, Seiten 606-607

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012105879A1 (de) 2012-07-02 2014-01-02 Oxea Gmbh Verfahren zur Herstellung von Isononylderivaten
DE102012105874A1 (de) 2012-07-02 2014-01-02 Oxea Gmbh Verfahren zur Herstellung von Isononansäurevinylestern
DE102012014396A1 (de) 2012-07-13 2014-01-16 Oxea Gmbh Vinylester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu seiner Herstellung sowie seine Verwendung
US9334225B2 (en) 2012-07-13 2016-05-10 Oxea Gmbh Vinyl esters of isononanoic acid starting from 2-ethyl hexanol, methods for the production thereof and use thereof
DE102014013123A1 (de) 2014-08-30 2016-03-03 Oxea Gmbh Verfahren zur Herstellung von Gemischen enthaltend tertiäre lsononansäuren ausgehend von 2-Ethylhexanol
US9695100B1 (en) 2014-08-30 2017-07-04 Oxea Gmbh Method for the production of mixtures containing tertiary isononanoic acids based on 2-ethylhexanol
DE102014013123B4 (de) 2014-08-30 2020-01-02 Oxea Gmbh Verfahren zur Herstellung von Gemischen enthaltend tertiäre lsononansäuren ausgehend von 2-Ethylhexanol

Also Published As

Publication number Publication date
EP2812307A1 (de) 2014-12-17
JP6041904B2 (ja) 2016-12-14
BR112014019187A2 (enExample) 2017-06-20
CN104487411A (zh) 2015-04-01
BR112014019187B1 (pt) 2020-01-21
KR20140113708A (ko) 2014-09-24
IN2014KN01079A (enExample) 2015-10-09
ES2669520T3 (es) 2018-05-28
PL2812307T3 (pl) 2018-07-31
BR112014019187A8 (pt) 2017-07-11
US9174922B2 (en) 2015-11-03
TWI461400B (zh) 2014-11-21
JP2015508064A (ja) 2015-03-16
KR101988210B1 (ko) 2019-06-13
TW201343624A (zh) 2013-11-01
US20140343310A1 (en) 2014-11-20
HK1203189A1 (en) 2015-10-23
WO2013117294A1 (de) 2013-08-15
EP2812307B1 (de) 2018-03-14

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Legal Events

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R012 Request for examination validly filed
R016 Response to examination communication
R016 Response to examination communication
R081 Change of applicant/patentee

Owner name: OQ CHEMICALS GMBH, DE

Free format text: FORMER OWNER: OXEA GMBH, 46147 OBERHAUSEN, DE

R016 Response to examination communication
R002 Refusal decision in examination/registration proceedings
R003 Refusal decision now final