DE102012002274A1 - Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten - Google Patents

Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten Download PDF

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Publication number
DE102012002274A1
DE102012002274A1 DE201210002274 DE102012002274A DE102012002274A1 DE 102012002274 A1 DE102012002274 A1 DE 102012002274A1 DE 201210002274 DE201210002274 DE 201210002274 DE 102012002274 A DE102012002274 A DE 102012002274A DE 102012002274 A1 DE102012002274 A1 DE 102012002274A1
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Prior art keywords
acid
formula
reaction
transition metal
process according
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DE201210002274
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German (de)
English (en)
Inventor
Leif Johnen
Dr. Strutz Heinz
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Oxea GmbH
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OQ Chemicals GmbH
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Priority to DE201210002274 priority Critical patent/DE102012002274A1/de
Priority to HK15102927.7A priority patent/HK1202523B/xx
Priority to KR1020147021633A priority patent/KR101994082B1/ko
Priority to PL13700621T priority patent/PL2812306T3/pl
Priority to IN1146KON2014 priority patent/IN2014KN01146A/en
Priority to JP2014555117A priority patent/JP6054424B2/ja
Priority to PCT/EP2013/000142 priority patent/WO2013117295A1/de
Priority to US14/372,235 priority patent/US9174921B2/en
Priority to ES13700621.9T priority patent/ES2627934T3/es
Priority to EP13700621.9A priority patent/EP2812306B1/de
Priority to CN201380006817.3A priority patent/CN104379550B/zh
Priority to BR112014019189A priority patent/BR112014019189B1/pt
Priority to TW102104106A priority patent/TWI461401B/zh
Publication of DE102012002274A1 publication Critical patent/DE102012002274A1/de
Withdrawn legal-status Critical Current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
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
    • 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
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
    • C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
DE201210002274 2012-02-06 2012-02-06 Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten Withdrawn DE102012002274A1 (de)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DE201210002274 DE102012002274A1 (de) 2012-02-06 2012-02-06 Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten
HK15102927.7A HK1202523B (en) 2012-02-06 2013-01-18 Transvinylation as a first stage of coupling production of vinyl esters and acetic acid or propionic acid reaction products
KR1020147021633A KR101994082B1 (ko) 2012-02-06 2013-01-18 비닐 에스테르와 아세트산 또는 프로피온산 반응 생성물들의 커플링 생성의 제1 스테이지로서의 비닐교환
PL13700621T PL2812306T3 (pl) 2012-02-06 2013-01-18 Transwinylowanie jako pierwszy etap sprzężonej produkcji estrów winylowych i następczych produktów z kwasu octowego lub kwasu propionowego
IN1146KON2014 IN2014KN01146A (https=) 2012-02-06 2013-01-18
JP2014555117A JP6054424B2 (ja) 2012-02-06 2013-01-18 ビニルエステル及び酢酸又はプロピオン酸反応生成物の共製造の第一段階としてのトランスビニル化
PCT/EP2013/000142 WO2013117295A1 (de) 2012-02-06 2013-01-18 Transvinylierung als erste stufe einer koppelproduktion von vinylestern und essigsäure- oder propionsäurefolgeprodukten
US14/372,235 US9174921B2 (en) 2012-02-06 2013-01-18 Transvinylation as a first stage of coupling production of vinyl esters and acetic acid or propionic acid reaction products
ES13700621.9T ES2627934T3 (es) 2012-02-06 2013-01-18 Transvinilización como primera etapa de una producción acoplada de productos de reacción de ésteres vinílicos y ácidos acéticos o ácidos propiónicos
EP13700621.9A EP2812306B1 (de) 2012-02-06 2013-01-18 Transvinylierung als erste stufe einer koppelproduktion von vinylestern und essigsäure- oder propionsäurefolgeprodukten
CN201380006817.3A CN104379550B (zh) 2012-02-06 2013-01-18 作为联合生产乙烯酯和乙酸或丙酸反应产物的第一阶段的转乙烯化反应
BR112014019189A BR112014019189B1 (pt) 2012-02-06 2013-01-18 transvinila ção como primeira etapa de uma produção por acoplamento de ésteres vinílicos e produtos de reação de ácido acético ou ácido propiônico
TW102104106A TWI461401B (zh) 2012-02-06 2013-02-04 乙烯酯之共同製法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE201210002274 DE102012002274A1 (de) 2012-02-06 2012-02-06 Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten

Publications (1)

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DE102012002274A1 true DE102012002274A1 (de) 2013-08-08

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DE201210002274 Withdrawn DE102012002274A1 (de) 2012-02-06 2012-02-06 Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten

Country Status (12)

Country Link
US (1) US9174921B2 (https=)
EP (1) EP2812306B1 (https=)
JP (1) JP6054424B2 (https=)
KR (1) KR101994082B1 (https=)
CN (1) CN104379550B (https=)
BR (1) BR112014019189B1 (https=)
DE (1) DE102012002274A1 (https=)
ES (1) ES2627934T3 (https=)
IN (1) IN2014KN01146A (https=)
PL (1) PL2812306T3 (https=)
TW (1) TWI461401B (https=)
WO (1) WO2013117295A1 (https=)

Cited By (3)

* 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
WO2026080677A1 (en) * 2024-10-09 2026-04-16 Braskem S.A. Monomer recovery system and process for obtaining a purified branched vinyl ester stream

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013224491A1 (de) 2013-11-29 2015-06-03 Wacker Chemie Ag Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102013224496A1 (de) 2013-11-29 2015-06-03 Wacker Chemie Ag Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102014206916A1 (de) 2014-04-10 2015-10-15 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
DE102015216373A1 (de) 2015-08-27 2017-03-02 Wacker Chemie Ag Verfahren zur katalytischen Umvinylierung von Carbonsäuren
EP3467050A1 (en) * 2017-10-04 2019-04-10 Omya International AG Coating compositions comprising ground natural calcium carbonate (gcc)

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
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
DE10030040C1 (de) * 2000-06-17 2001-10-31 Celanese Chem Europe Gmbh Verfahren zur Gewinnung von Wertstoffen aus Abfallgemischen chemischer Produktionsprozesse
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
JP2002322127A (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
WO2011139360A1 (en) 2010-05-04 2011-11-10 Celanese International Corporation Process for the continuous transvinylation of carboxylic acids with vinyl acetate

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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
GB8319619D0 (en) * 1983-07-20 1983-08-24 Bp Chem Int Ltd Acetic anhydride
ECSP910793A (es) * 1990-11-30 1992-12-21 Union Carbide Chem Plastics Co Inc La tecnologia de transvinilacion ayudada azeotropica
IN191266B (https=) * 1999-09-16 2003-10-18 Council Scient Ind Res
KR20120086717A (ko) * 2009-10-26 2012-08-03 셀라니즈 인터내셔날 코포레이션 산성 촉매를 사용하여 아세트산으로부터 에탄올을 제조하는 방법

Patent Citations (17)

* 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
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
DE10030040C1 (de) * 2000-06-17 2001-10-31 Celanese Chem Europe Gmbh Verfahren zur Gewinnung von Wertstoffen aus Abfallgemischen chemischer Produktionsprozesse
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
JP2002322127A (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
WO2011139360A1 (en) 2010-05-04 2011-11-10 Celanese International Corporation Process for the continuous transvinylation of carboxylic acids with vinyl acetate
WO2011139361A1 (en) 2010-05-04 2011-11-10 Celanese International Corporation Process for the semi-continuous transvinylation of carboxylic acids with vinyl acetate

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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
Murray, Catalysis Today 1992, 13, Seiten 93-102
Ullmanns Encyclopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie GmbH, Band 11, Seite 71
Ullmanns Encyclopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie GmbH, Band 11, Seite 71; Band 19, Seite 457
Ullmanns Encyclopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie GmbH, Band 11, Seiten 68-70; Band 19, Seiten 457-458
Ullmanns Encyclopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie GmbH, Band 19, Seite 457
Ullmanns Encyclopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie GmbH, Band 23, Seiten 601-605
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
Weissermel, Arpe, Industrielle organische Chemie, 3. Auflage, VCH, 1988, Seite 191
Weissermel, Arpe, Industrielle organische Chemie, 3. Auflage, VCH, 1988, Seiten 191; Ullmanns Encyclopädie der technischen Chemie, 4. Auflage, 1983, Verlag Chemie GmbH, Band 19, Seiten 458
Weissermel, Arpe, Industrielle organische Chemie, 3. Auflage, VCH, 1988, Seiten 193-194

Cited By (3)

* 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
WO2026080677A1 (en) * 2024-10-09 2026-04-16 Braskem S.A. Monomer recovery system and process for obtaining a purified branched vinyl ester stream

Also Published As

Publication number Publication date
JP6054424B2 (ja) 2016-12-27
TWI461401B (zh) 2014-11-21
IN2014KN01146A (https=) 2015-10-16
CN104379550B (zh) 2016-08-24
KR101994082B1 (ko) 2019-07-01
US9174921B2 (en) 2015-11-03
PL2812306T3 (pl) 2017-09-29
TW201341355A (zh) 2013-10-16
JP2015512868A (ja) 2015-04-30
KR20140122716A (ko) 2014-10-20
BR112014019189A2 (https=) 2017-06-20
CN104379550A (zh) 2015-02-25
EP2812306A1 (de) 2014-12-17
BR112014019189B1 (pt) 2020-01-21
EP2812306B1 (de) 2017-03-22
ES2627934T3 (es) 2017-08-01
US20140357881A1 (en) 2014-12-04
WO2013117295A1 (de) 2013-08-15
BR112014019189A8 (pt) 2017-07-11
HK1202523A1 (zh) 2015-10-02

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