KR960700993A - 카르보닐화 방법(carbonylation process) - Google Patents

카르보닐화 방법(carbonylation process) Download PDF

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KR960700993A
KR960700993A KR1019950703268A KR19950703268A KR960700993A KR 960700993 A KR960700993 A KR 960700993A KR 1019950703268 A KR1019950703268 A KR 1019950703268A KR 19950703268 A KR19950703268 A KR 19950703268A KR 960700993 A KR960700993 A KR 960700993A
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드렌트 아이트
험프레이 루이스 펠로 데니스
하셀라 메리스
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알베르투스 빌헬무스·요아네스 째스트라텐
셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이
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    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
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    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
    • B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
    • B01J31/248—Bridged ring systems, e.g. 9-phosphabicyclononane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
    • C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J2531/824—Palladium

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Abstract

본 발병은 하기 일반식(I)의 이좌배위 리간드 및 팔라듐 화합물을 기재로한 실질적인 비-산성촉매 시스템의 존재하에 일산화탄소 및 공-반응물과의 반응으로써 에틸렌성으로 불포화된 화합물을 카를보닐화시키는 방법을 제공한다:
P1R2M1RM2R3R4(I)
여기서, M1 및 M2는 각각 인, 비소 또는 안티몬 원자를 나타내고, R은 2가 유기 브릿징기를 나타내고, R1, R2, R3 및 R4는 각각 치환 또는 비-치환 지방족 기를 나타내고, 이로써 두 자유 원자가는 M1 또는 M2각각에 연결된다. 게다가 본 발명은 a)팔라듐 화합물 : b)하기 일반식의 이좌배위 리간드
P1R2PRPR3R4(II)
여기서 R은 브릿지내 1-10 원자를 함유하는 이좌배우 유기 브릿징기이고 R1, R2, R3및 R4는 각각 치환 또는 비-치환 지방족 기를 나타내며, 단 R2와 함께 R1및/또는 R4와 함께 R3는 적어도 6고리 원자를 가진 이좌배우 시클릭 기를 나타내고, 이로써 두 자유 원자가는 인 원자에 연결된다; 및 c)염기성 화합물로 구성되는 촉매 조성물을 제공한다.

Description

카르보닐화 방법(CARBONYLATION PROCESS)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 하기 일반식의 이좌 배위 리간드 및 팔라듐 화합물을 기재로한 실질적으로 비-산성 촉매 시스템의 존재하에 일산화탄소 및 공-반응물과 반응으로써 에틸렌성으로 불포화된 화합물을 카르보닐화시키는 방법.
    P1R2M1RM2R3R4(I)
    여기서, M1및 M2는 각각 인, 비소 또는 안티몬 원자를 나타내고, R은 2가 유기 브릿징기를 나타내고, R1, R2, R3및 R4는 각각 치환 또는 비-치환 지방족 기를 나타내며, 단 R2와 함께 R1및/또는 R4와 함께 R3는 적어도 5고리 원자를 가진 2가 시클릭 기를 나타내고, 이로써 두 자유 원자가는 M1또는 M2각각에 연결된다.
  2. 제1항에 있어서, M1및 M2모두가 인 원자를 나타내는 방법.
  3. 제1 또는 2항에 있어서, R이 브릿지내 1-10 원자를 함유하는 2가 유기 브릿징기를 나타내는 방법.
  4. 제1-3항중 어느 한 항에 있어서, R이 에틸렌기를 나타내는 방법.
  5. 제1-4항중 어느 한 항에 있어서, R2와 함께 R1및/또는 R4와 함께 R3로 표현되는 2가 시클릭기가 6-9고리 원자를 가지는 시클로알킬렌기인 방법.
  6. 제5항에 있어서, R이, 각각이 9-포스파비시클로노닐기의 [4, 2, 1] 및/또는 [3, 3, 1] 이성질체에 참여하는 두 인 원자에 연결되는 방법.
  7. 제1-6항 중 어느 한 항에 있어서, 반응이 염기성 화합물의 존재하에 수행되는 방법.
  8. 제7항에 있어서, 염기성 화합물 피리딘으로서, 치환된 피리딘 또는 트리알킬아민이 사용되는 방법.
  9. 제1-8항 중 어느 한 항에 있어서, 반응이 액체 희석제의 존재하 또는 수행되는 방법.
  10. 제9항에 있어서, 희석제로서 에테르 특히 디에틸렌 글리콜의 테트라히드로푸란 또는 디메틸에트르가 사용되는 방법.
  11. a)팔라듐 화합물: b)하기 일반식의 이좌배위 리간드
    P1R2PRPR3R4(II)
    여기서 R은 브릿지내 1-10 원자를 함유하는 이좌배우 유기 브릿징기이고 R1, R2, R3및 R4는 각각 치환 또는 비-치환 지방족 기를 나타내며, 단 R2와 함께 R1및/또는 R4와 함께 R3는 적어도 6고리 원자를 가진 이좌배우 시클릭 기를 나타내고, 이로써 두 자유 원자가는 인 원자에 연결된다; 및 c)염기성 화합물로 구성되는 촉매 조성물을 제공한다.
  12. 제11항에 있어서, P1R2P 및 R3R4P는 각각이 9- 포스파비시클로노닐 기의 [4, 2, 1] 및/또는 [3, 3, 1] 이성질체를 나타내고, 염기성 화합물을 피리딘, 치환된 피리딘 또는 트리알킬아민인 촉매 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950703268A 1993-02-09 1994-02-07 카르보닐화 방법 KR100286535B1 (ko)

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Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5719313A (en) * 1995-03-16 1998-02-17 Shell Oil Company Carbonylation catalyst system and a process for the carbonylation of acetylenically unsaturated compounds
US6103927A (en) * 1996-04-16 2000-08-15 Shell Oil Company Process for the carbonylation of ethylenically unsaturated compounds
US6037506A (en) * 1998-09-18 2000-03-14 Shell Oil Company Hydroformylation process
TW524801B (en) * 1999-03-22 2003-03-21 Shell Int Research Process for the carbonylation of conjugated dienes
US6548716B1 (en) 2000-03-22 2003-04-15 Shell Oil Company Process for preparing a 1,3-diol
IT1318712B1 (it) 2000-08-01 2003-08-27 Graziano Vignali Composizione colorante per materiali ceramici e relativo processo dicolorazione.
DE10048874A1 (de) 2000-09-29 2002-04-11 Basf Ag Katalysatorsystem und Verfahren zur Carbonylierung
DE10228293A1 (de) 2001-07-28 2003-02-13 Basf Ag Verfahren zur Herstellung von Dialkylketonen
WO2005003070A1 (en) 2003-07-03 2005-01-13 Lucite International Uk Limited Process for the hydroformylation of ethylenically unsaturated compounds
GB0403592D0 (en) 2004-02-18 2004-03-24 Lucite Int Uk Ltd A catalyst system
GB0411951D0 (en) * 2004-05-28 2004-06-30 Lucite Int Uk Ltd Carbonylation of ester
US20110167841A1 (en) 2004-06-04 2011-07-14 Brasscorp Limited Compositions and methods for injection of sealants and/or drying agents into air conditioning and refrigeration systems
US7296423B2 (en) * 2004-06-04 2007-11-20 Brasscorp Limited Composition and methods for injection of sealants into air conditioning and refrigeration systems
GB0516556D0 (en) 2005-08-12 2005-09-21 Lucite Int Uk Ltd Improved catalyst system
CA2626107C (en) 2005-11-17 2016-06-21 Lucite International Uk Limited Carbonylation of ethylenically unsaturated compounds
GB0607494D0 (en) 2006-04-13 2006-05-24 Lucite Int Uk Ltd Metal complexes
BRPI0719344B1 (pt) * 2006-12-02 2017-05-02 Lucite Int Uk Ltd ligando bidentado, processo para a carbonilação de compostos etilenicamente insaturados, e, sistema de catalisador
GB0625518D0 (en) * 2006-12-21 2007-01-31 Lucite Int Uk Ltd Carbonylation of conjugated dienes
GB0812297D0 (en) * 2008-07-04 2008-08-13 Lucite Int Uk Ltd Novel carbonylation ligand sand thier use of in the carbonylation of ethylenically unsaturated compounds
EP2334994A4 (en) * 2008-09-11 2013-11-06 Brasscorp Ltd COMPOSITIONS AND METHOD FOR INJECTING SEALING AND / OR DRYING AGENTS IN AIR-CONDITIONING OR COOLING SYSTEMS
JP5813625B2 (ja) * 2009-04-23 2015-11-17 ヴイティーユー ホールディング ゲーエムベーハーＶｔｕ Ｈｏｌｄｉｎｇ Ｇｍｂｈ イオン性液体を脱水する方法
GB201000078D0 (en) 2010-01-05 2010-02-17 Lucite Int Uk Ltd Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1127965A (en) * 1965-11-26 1968-09-25 Shell Int Research Ditertiary phosphines and application thereof as catalyst components for alcohol production
US4172087A (en) * 1978-02-13 1979-10-23 Texaco Development Corporation Process for preparing unsaturated aliphatic esters from aliphatic dienes
GB2058074B (en) * 1979-08-23 1983-10-12 Secr Defence Palladium complexes
EP0055875B1 (en) * 1981-01-06 1986-08-20 Shell Internationale Researchmaatschappij B.V. Process for the carbonylation of olefins
DE3332018A1 (de) * 1983-09-06 1985-03-21 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von bernsteinsaeurediestern
GB2183631A (en) * 1985-11-27 1987-06-10 Shell Int Research Process for the preparation of oxo-alkanedioic acids or diesters thereof
GB2185740A (en) * 1986-01-27 1987-07-29 Shell Int Research Process for the preparation of ketones
KR880007426A (ko) * 1986-12-24 1988-08-27 오노 알버어스 팔라듐 촉매를 사용한 올레핀형 불포화 화합물의 카르보닐화 방법
GB9002521D0 (en) * 1990-02-05 1990-04-04 Shell Int Research Carbonylation catalyst system
EP0495547B1 (en) * 1991-01-15 1996-04-24 Shell Internationale Researchmaatschappij B.V. Carbonylation of olefins

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DE69405713T2 (de) 1998-01-08
JPH08506575A (ja) 1996-07-16
EP0683764A1 (en) 1995-11-29
CN1041517C (zh) 1999-01-06
WO1994018154A1 (en) 1994-08-18
KR100286535B1 (ko) 2001-04-16
DE69405713D1 (en) 1997-10-23
CN1117726A (zh) 1996-02-28
CA2155574C (en) 2004-07-27
ES2108429T3 (es) 1997-12-16
US5436356A (en) 1995-07-25
JP3827323B2 (ja) 2006-09-27
CA2155574A1 (en) 1994-08-18
EP0683764B1 (en) 1997-09-17

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