KR900014032A - 카르보닐화 촉매 시스템 및 신규 포스핀과 그의 제조방법 - Google Patents

카르보닐화 촉매 시스템 및 신규 포스핀과 그의 제조방법 Download PDF

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KR900014032A
KR900014032A KR1019900002672A KR900002672A KR900014032A KR 900014032 A KR900014032 A KR 900014032A KR 1019900002672 A KR1019900002672 A KR 1019900002672A KR 900002672 A KR900002672 A KR 900002672A KR 900014032 A KR900014032 A KR 900014032A
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catalyst system
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general formula
atom
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드렌트 아이트
헨리쿠스 마리아 부트젤라르 페투루스
바베 야거 빌렘
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오노 알버어스
셀 인터나쵸나아레 레사아치 마아츠 샤피 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
    • B01J31/16—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
    • B01J31/189—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 containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
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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
    • B01J31/24—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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0013—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group without a metal-carbon linkage
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006—Palladium compounds
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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    • C07F9/576—Six-membered rings
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    • 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
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    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
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    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
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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
    • B01J31/18—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
    • B01J31/1805—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 nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine

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Abstract

내용 없음

Description

카르보닐화 촉매 시스템 및 신규 포스핀과 그의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 하기 (a) 및 (b)로 구성되는 촉매 시스템 : a) Ⅷ족 금속원, 및 b) 하기 일반식 (Ⅰ)의 포스핀 또는 그들의 산부가염 :
    상기 식에서, R¹, R² 및 R³는 임의로 치환된 아릴기 및 일반식 (Ⅱ) :의 기중에서 독립적으로 선택되고, 상기 일반식 (Ⅱ)에서 A, X, Y 및 Z 각각은 질소원자, CH기 및 R이 히드록실기, 아미노기, 아미도기, 시아노기, 아실기, 아실록시기, 할로겐원자, 임의로 치환된 히드로카르빌기 또는 임의로 치환된 히드로카르빌록시기를 나타내는 일반식 CR의 기중에서 독립적으로 선택되고, 인접한 두 개의 CR기는 고리를 형성할 수도 있으며, 단, 상기 일반식 (Ⅰ)에서 R¹, R² 또는 R³ 중 적어도 하나는 A와 Z중 적어도 하나가 일반식 CR의 기를 나타내는 상기 일반식 (Ⅱ)의 기를 나타내어야 한다.
  2. 제1항에 있어서, Z기가 일반식 CR의 기를 나타내는 촉매 시스템.
  3. 제1항 내지 제2항에 있어서, A, X 및 Y 각각이 CH기 및 일반식 CR의 기로부터 독립적으로 선택되는 촉매 시스템.
  4. 제1항 내지 제3항 중 어느 한 항에 있어서, R¹, R² 또는 R³로 나타내어진 임의의 아릴기가 임의로 치환된 페닐기인 촉매 시스템.
  5. 제1항 내지 제4항중 어느 한 항에 있어서, 각각의 R기가 할로겐 원자, C1-4알킬기 및 C1-4알콕시기로부터 독립적으로 선택되는 촉매 시스템.
  6. 제1항 내지 제5항중 어느 한 항에 있어서, Ⅷ족 금속원이 팔라듐 화합물인 촉매 시스템.
  7. 제1항 내지 제6항중 어느 한 항에 있어서, Ⅷ족 금속원자 그램 당 일반식 (Ⅰ)의 포스핀의 몰수가 2-500인 촉매 시스템.
  8. 제1항 내지 제7항중 어느 한 항에 있어서, 양성자산이 일반식 (Ⅰ)의 포스핀 당량 당 0.5-5당량의 양으로 존재하는 촉매 시스템.
  9. 비스(6-에톡시-2-피리딜)페닐포스핀, 비스(6-클로로-2-피리딜) 페닐포스핀, 및 비스(6-브로모-2-피리딜) 페닐포스핀은 제외하고, 제1항에 정의된 일반식 (Ⅰ)의 포스핀 또는 그들의 산 부가 염.
  10. 하기 일반식 (Ⅲ)의 포스포러스 화합물 :
    (상기 식에서, M¹은 금속원자 또는 이탈원자 또는 이탈기를 나타내고, R² 및 R³는 제1항에 주어진 의미를 가진다)을 하기 일반식(Ⅳ)의 적절한 화합물 :
    M²―R¹ (Ⅳ)
    (상기 식에서, M²는 금속원자 또는 이탈원자 또는 이탈기를 나타내고, R¹은 제1항에 주어진 의미를 가진다)과 반응시키고, 임의로 산 부가염을 형성시키는 것으로 구성되는 제9항에 정의된 포스핀 또는 그들의 산 부가염의 제조 방법.
  11. 아세틸렌형 또는 올레핀형 불포화 탄화수소의 카르보닐화에서의 제1항에 정의된 촉매시스템의 사용.
  12. 제1항에 정의된 카르보닐화 촉매 시스템 존재하에 액상에서 일산화탄소 및 히드록실-함유 화합물과 알파 아세틸렌을 반응시키는 것으로 구성되는, 알파, 베타-올레핀형 불포화 화합물의 제조방법.
  13. 제12항에 있어서, 하기 a)- c)로 구성되는 카르보닐화 촉매 시스템의 제조방법 : a) 팔라듐 화합물, b) 제1항에 정의된 일반식 (Ⅰ)의 포스핀, 및 c) 양성자산.
  14. 제12항 또는 제13항에 있어서, 일산화탄소 및 메탄올과 프로핀과의 반응으로 메틸 메타클릴레이트를 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900002672A 1989-03-03 1990-02-28 카르보닐화촉매시스템 KR0144567B1 (ko)

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Application Number Priority Date Filing Date Title
GB898904860A GB8904860D0 (en) 1989-03-03 1989-03-03 Process for the preparation of olefinically unsaturated compounds
GB8904860.7 1989-03-03
GB9002508.1 1990-02-05
GB909002508A GB9002508D0 (en) 1990-02-05 1990-02-05 Carbonylation catalyst system

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KR900014032A true KR900014032A (ko) 1990-10-22
KR0144567B1 KR0144567B1 (ko) 1998-07-15

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US (1) US5158921A (ko)
EP (1) EP0386833B1 (ko)
JP (1) JP3051986B2 (ko)
KR (1) KR0144567B1 (ko)
CN (1) CN1042400C (ko)
AU (1) AU624483B2 (ko)
BR (1) BR9000965A (ko)
CA (1) CA2011292C (ko)
DE (1) DE69033159T2 (ko)
ES (1) ES2133137T3 (ko)
SG (1) SG50547A1 (ko)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9111583D0 (en) * 1991-05-30 1991-07-24 Shell Int Research Carbonylation catalyst system
US5258546A (en) * 1991-05-30 1993-11-02 Shell Oil Company Carbonylation catalyst system
DE4141299C2 (de) * 1991-12-14 2000-09-21 Celanese Chem Europe Gmbh Verfahren zur Herstellung von tertiären Phosphanen
SG49630A1 (en) * 1992-04-08 1998-06-15 Shell Int Research Carbonylation process using palladium phosphine catalyst
US5414109A (en) * 1993-03-19 1995-05-09 Shell Oil Company Process for the carbonylation of acetylenically unsaturated compounds
EP0724558B1 (en) * 1993-08-19 1998-04-29 Shell Internationale Researchmaatschappij B.V. Process for the carbonylation of acetylenically unsaturated compounds
CN1035114C (zh) * 1994-04-26 1997-06-11 周毕华 柴油乳化剂
US5719313A (en) * 1995-03-16 1998-02-17 Shell Oil Company Carbonylation catalyst system and a process for the carbonylation of acetylenically unsaturated compounds
DE19548399A1 (de) * 1995-12-22 1997-06-26 Basf Ag Rutheniumkomplexe mit einem chiralen, zweizähnigen Phosphinoxazolin-Liganden zur enantioselektiven Transferhydrierung von prochiralen Ketonen
TW414789B (en) * 1996-03-26 2000-12-11 Shell Int Research Process for the carbonylation of acetylenically unsaturated compounds
DE19983354C2 (de) * 1998-07-08 2002-08-08 Neste Chemicals Oy Espoo Verfahren zur Hydroformylierung
FI20002807A0 (fi) * 2000-09-05 2000-12-20 Neste Chemicals Oy Menetelmä alkeenien hydroformyloimiseksi
US6660883B1 (en) * 2000-09-14 2003-12-09 Council Of Scientific And Industrial Research Process for the preparation of 2-aryl propionic acids
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
GB0218613D0 (en) * 2002-08-10 2002-09-18 Lucite Int Uk Ltd Process for the carbonylation of ethylenically unsaturated compounds
TWI301481B (en) 2002-08-10 2008-10-01 Lucite Int Uk Ltd A catalyst system
DE10313319A1 (de) * 2003-03-25 2004-10-07 Basf Ag Verfahren zur Hydroformylierung
JP2007516197A (ja) 2003-07-03 2007-06-21 ルーサイト インターナショナル ユーケー リミテッド エチレン性不飽和化合物のヒドロホルミル化方法
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
GB0516556D0 (en) 2005-08-12 2005-09-21 Lucite Int Uk Ltd Improved catalyst system
KR101633325B1 (ko) 2005-11-17 2016-06-24 루사이트 인터내셔널 유케이 리미티드 에틸렌성 불포화 화합물의 카르보닐화
GB0607494D0 (en) 2006-04-13 2006-05-24 Lucite Int Uk Ltd Metal complexes
GB2437930A (en) * 2006-05-10 2007-11-14 Lucite Int Uk Ltd Mixing apparatus
WO2008065448A1 (en) * 2006-12-02 2008-06-05 Lucite International Uk Limited Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds
GB0625518D0 (en) * 2006-12-21 2007-01-31 Lucite Int Uk Ltd Carbonylation of conjugated dienes
GB0713624D0 (en) * 2007-07-13 2007-08-22 Lucite Int Uk Ltd Improved solvent for catalyst system
KR101632449B1 (ko) 2008-03-25 2016-06-21 수미토모 케미칼 컴퍼니 리미티드 알콕시카보닐 화합물의 제조 방법
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
GB0921875D0 (en) 2009-12-15 2010-01-27 Lucite Int Uk Ltd A continuous process for the carbonylation of ethylene
GB0921876D0 (en) 2009-12-15 2010-01-27 Lucite Int Uk Ltd Improved carbonylation process
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
CN102190583A (zh) * 2010-03-08 2011-09-21 中国科学院成都有机化学有限公司 一种钯膦络合物催化乙炔羰基合成丙烯酸低碳醇酯的方法
GB201122054D0 (en) 2011-12-21 2012-02-01 Lucite Int Uk Ltd A continuous process for the carbonylation of ethylene
JP2013193992A (ja) 2012-03-21 2013-09-30 Sumitomo Chemical Co Ltd メタクリル酸アルキルの製造方法
DE102013210840A1 (de) * 2013-06-11 2014-12-11 Evonik Industries Ag Synthese von a,ß-ungesättigten Carbonsäuren (Meth)acrylaten aus Olefinen und CO2
CN104707663B (zh) * 2013-12-11 2017-07-18 中国科学院大连化学物理研究所 一种有机配体聚合物载体及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4257973A (en) * 1971-11-05 1981-03-24 E. I. Du Pont De Nemours And Company Process of making acids or esters from unsaturated compounds
US3887595A (en) * 1973-03-05 1975-06-03 Shell Oil Co Carbonylation process
GB8432376D0 (en) * 1984-12-21 1985-02-06 Shell Int Research Carbonylation of acetylenically unsaturated compounds
GB8501919D0 (en) * 1985-01-25 1985-02-27 Shell Int Research Carbonylation of allenically unsaturated compounds
ATE77383T1 (de) * 1985-10-18 1992-07-15 Hoffmann La Roche Chirale rhodium-diphosphinkomplexe fuer asymmetrische hydrierungen.
CA1305695C (en) * 1986-08-22 1992-07-28 Eit Drent Catalyst compositions and process for olefin/co copolymerization
CA1331173C (en) * 1986-12-05 1994-08-02 Eit Drent Process for the carbonylation of acetylenically unsaturated compounds
GB8705699D0 (en) * 1987-03-11 1987-04-15 Shell Int Research Carbonylation of olefinically unsaturated compounds
US4880902A (en) * 1987-08-27 1989-11-14 Shell Oil Company Copolymerization of carbon monoxide and olefin with diphosphine having heterocyclic substituents as catalyst

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EP0386833B1 (en) 1999-06-16
KR0144567B1 (ko) 1998-07-15
EP0386833A1 (en) 1990-09-12
CA2011292A1 (en) 1990-09-03
AU624483B2 (en) 1992-06-11
CN1045234A (zh) 1990-09-12
JP3051986B2 (ja) 2000-06-12
CA2011292C (en) 2000-09-19
CN1042400C (zh) 1999-03-10
BR9000965A (pt) 1991-02-19
DE69033159T2 (de) 1999-11-18
SG50547A1 (en) 1998-07-20
DE69033159D1 (de) 1999-07-22
JPH02277551A (ja) 1990-11-14
AU5063190A (en) 1990-09-06

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