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KR910000764A - 술폰화된 페닐 포스판류를 함유하는 착화합물 - Google Patents

술폰화된 페닐 포스판류를 함유하는 착화합물 Download PDF

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Publication number
KR910000764A
KR910000764A KR1019890017637A KR890017637A KR910000764A KR 910000764 A KR910000764 A KR 910000764A KR 1019890017637 A KR1019890017637 A KR 1019890017637A KR 890017637 A KR890017637 A KR 890017637A KR 910000764 A KR910000764 A KR 910000764A
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South Korea
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complex
catalyst
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group
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KR930003868B1 (ko
Inventor
헤르만 볼프강 아
쿨페 윌겐
켈너 윌겐
리에플 헤르베르트
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콘콜, 라이첼트
훽스트 악치엔 게젤샤프트
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Priority claimed from DE3921295A external-priority patent/DE3921295A1/de
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Abstract

내용없음

Description

술폰화된 페닐 포스판류를 함유하는 착화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (21)

  1. 비스(1, 5-시클로옥타디엔) 니켈과 트리스(m-술포페닐)포스판의 트리소듐염의 반응 생성물은 제외하며, 착 리간드로서 트리스(m-술포페닐)포스판의 트리소듐염과 경우에 따라서는 다른 리간드들을 함유함을 특징으로 하는 주기율표의 Ⅶ A족, Ⅷ A족 및 Ⅰ B족 원소들의 착화합물.
  2. 제 1항에 있어서, 하기 일반식에 대응하는 착화합물.
  3. L1 wL2 xMy〔P(C6H4-m-SO3Na)3〕2
  4. 〔상기식에서, L1및 L2는 동일하거나 다르며, 트리스(m-술포페닐)포스판의 트리소듐염 이외에 착화합물의 중앙 원소에 결합될 수 있는 리간드이며; M은 중앙 원자로서 주기율표의 Ⅶ A족, Ⅷ A족 및 ⅠB족 원소를 표시하고; w, x, y 및 z는 정수이고, w 및 x는 각각 0내지 7y이고 y는 1내지 6이며 z는 ≤ 4이다.〕
  5. 제 2항에 있어서, 트리스(m-술포페닐)포스판의 트리소듐염 이외에 더 이상의 리간드로서 H, CO, NO, PF3, H2O, S, 할로겐, π-방향족 리간드, π-올레핀 리간드, 및/또는 π-아세틸렌 리간드를 함유하는 특징으로 하는 착화합물.
  6. 제3항에 있어서, π-방향족 리간드가 시클로펜타디에닐임을 특징으로 하는 착화합물.
  7. 제3항에 있어서, π-올레핀 리간드가 시클로옥타디엔임을 특징으로 하는 착화합물.
  8. 제3항에 있어서, π-아세틸렌 리간드가 디페닐아세틸렌임을 특징으로 하는 착화합물.
  9. 제1또는 2항에 있어서, 중앙 금속이 망간, 철, 루테늄, 코발트, 로듐, 이리듐, 니켈, 팔라듐, 백금, 구리, 은 또는 금임을 특징으로 하는 착화합물.
  10. 제1또는 2항에 있어서, 하기식으로 표현됨을 특징으로 하는 착화합물.
  11. 망간화합물(n5-C5H5)Mn(CO)2〔P(C6H4-m-SO3Na3〕,(n5-C5H5)Mn(CO)〔P(C6H4-m-SO3Na3〕2또는철화합물Fe(CO)4〔P(C6H4-m-SO3Na3〕,Fe(CO)3〔P(C6H4-m-SO3Na3〕2,Fe4(CO)11〔P(C6H4-m-SO3Na3〕또는 루테늄 화합물 Ru(NO)2〔P(C6H4-m-SO3Na)3〕2,RuCl2〔P(C6H4-m-SO3Na)3〕2또는 코발트 화합물Co2(CO)6〔P(C6H4-m-SO3Na)3〕2,CoH(CO)〔P(C6H4-m-SO3Na)3〕3,CoH2〔P(C6H4-m-SO3Na)3〕3,Co2(CO)4(H5C6-C≡C-C6H5)〔P(C6H4-m-SO3Na)3〕2또는 로듐 화합물RhCl〔P(C|6H4-m-SO3Na)3〕3,Rh(NO)〔P(C6H4-m-SO3Na)3〕3,Rh(CH3COO)〔P(C6H4-m-SO3Na)3〕3,Rh(CO)(OH)〔P(C6H4-m-SO3Na)3〕2,Rh(CO)Cl〔P(C6H4-m-SO3Na)3〕2,Rhμ-Cl)(CO)〔P(C6H4-m-SO3Na)3〕2,Rh(OH)(H2O)〔P(C6H4-m-SO3Na)3〕3,Rh2〔P(C6H4-m-SO3Na)3〕2〔P(C6H4-m-SO3Na)2(C6H4-m-SO3)〕2,Rh(μ-Cl2)
  12. (n4-C8H12)〔P(C6H4-m-SO3Na)3〕2,Rh6(CO)7〔P(C6H4-m-SO3Na)3〕9,또는 어리듐 화합물Ir(NO)〔P(C6H4-m-SO3Na)3〕3,IrH(CO)〔P(C6H4-m-SO3Na)3〕3,Irμ-Cl)(n4C8H12)〔P(C6H4-m-SO3Na3〕2또는 니켈 화합물Ni〔P(C6H4-m-SO3Na)3〕3,Ni(CO)2〔P(C6H4-m-SO3Na)3〕2,Ni(PF3)2〔P(C6H4-m-SO3Na)3〕2,팔라듐 화합물Pd〔P(C6H4-m-SO3Na)3〕3또는백금 화합물Pt〔P(C6H4-m-SO3Na)3〕4,PtCl2〔P(C6H4-m-SO3Na)3〕2또는구리 화합물Cu3〔P(C6H4-m-SO3Na)3〕2〔μ-P(C6H4-m-SO3Na)2(C6H4-m-SO3)3또는 은 화합물Ag〔P(C6H4-m-SO3Na)3〕2〔P(C6H4-m-SO3Na)2(C6H4-m-SO3〕또는 금 화합물Au2〔P(C6H4-m-SO3Na)3〕2〔μ-P(C6H4-m-SO3)2(C6H4-m-SO3)〕3,Au2S〔P(C6H4-m-SO3Na)3〕2
  13. 수소화 반응 촉매로서 제 1내지 8항 중 어느 한 항에 따른 화합물의 용도.
  14. 물-기체 평형 조절용 촉매로서 제 1내지 8항 중 어느 한 항에 따른 화합물의 용도.
  15. 히드로카르보닐화 반응 촉매로서 제 1내지 8항 중 어느 한 항에 따른 화합물의 용도.
  16. 히드로포르밀화 반응 촉매로서 제 1항 내지 8항 중 어느 한 항에 따른 화합물의 용도.
  17. 산화 반응 촉매로서 제 1항 내지 8항 중 어느 한 항에 따른 화합물의 용도.
  18. 탄소-탄소 이중 결합을 탄소-탄소 다중 결합과 연결시키는 촉매로서 제 1내지 8항 중 어느 한 항에 따른 화합물의 용도.
  19. 제 14항에 있어서, 화합물을 알렌/알킨 커플링 반응 촉매로서 사용함을 특징으로 하는 용도.
  20. 탄소-탄소 이중 결합에 2차 아민을 부가시키는 촉매로서 제 1내지 8항 중 어느 한 항에 따른 화합물의 용도.
  21. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890017637A 1988-12-02 1989-11-30 술폰화된 페닐 포스판류를 함유하는 착화합물 Expired - Fee Related KR930003868B1 (ko)

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DEP3840600.4 1988-12-02
DE3840600A DE3840600A1 (de) 1988-12-02 1988-12-02 Sulfonierte phenylphosphane enthaltende komplexverbindungen
DE3921295A DE3921295A1 (de) 1989-06-29 1989-06-29 Sulfonierte phenylphosphane enthaltende komplexverbindungen
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Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5223648A (en) * 1990-12-17 1993-06-29 Hoechst Aktiengesellschaft Process for producing aldehydes
US5360459A (en) 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
JP2736947B2 (ja) * 1991-11-21 1998-04-08 高砂香料工業株式会社 水溶性なスルホン酸アルカリ金属塩置換ビナフチルホスフイン遷移金属錯体及びこれを用いた不斉水素化法
FR2693188B1 (fr) * 1992-07-01 1994-08-05 Beghin Say Eridania Procede de telomerisation de dienes conjugues avec des polyols et notamment avec des sucres et des derives de sucres.
BE1006455A3 (nl) * 1992-12-23 1994-08-30 Dsm Nv Werkwijze voor het bereiden van (meth)acrylonitril.
DE4321512C2 (de) * 1993-06-29 2001-10-04 Celanese Chem Europe Gmbh Verfahren zur Herstellung von sulfonierten Arylphosphinen
US5616749A (en) * 1994-09-27 1997-04-01 National Science Council Preparation of layered zirconium phosphite sulfophenylphosphonates and their use as a catalyst
US5536874A (en) * 1994-11-30 1996-07-16 Hoechst Celanese Corporation Process for preparing arylacetic acid and arylpropionic acid derivatives
US5650546A (en) * 1994-12-16 1997-07-22 Council Of Scientific Industrial Resear. Process for the catalytic hydrogenation of organic compounds
HUP9900235A3 (en) * 1995-07-25 1999-11-29 Clariant Produkte Deutschland Method of carrying out cross-coupling reactions
WO1997007087A1 (de) * 1995-08-14 1997-02-27 Clariant Gmbh Verfahren zur reduktion von nitroverbindungen
US5777087A (en) * 1996-04-18 1998-07-07 Celanese International Corporation Aryl diphosphines and catalysts containing the same
US5753584A (en) * 1996-06-04 1998-05-19 Intevep, S.A. Catalyst system for selective hydrogenation of heteroaromatic sulfur-containing and nitrogen-containing compounds
US5817775A (en) * 1996-10-10 1998-10-06 Celanese International Corporation Phosphines and catalysts containing the same
CN1046532C (zh) * 1996-10-15 1999-11-17 中国石油化工总公司 二[三(间－磺酸盐苯基)膦]一氯一羰基铑的制备方法
DE19701245C1 (de) 1997-01-16 1998-07-23 Celanese Gmbh Guanidiniumphosphane, ein Verfahren zu ihrer Herstellung und ihre Verwendung
DE19704479A1 (de) * 1997-02-06 1998-08-13 Cerdec Ag Dekorpräparat zur Herstellung goldhaltiger Dekore und deren Verwendung
US7083743B2 (en) * 1999-12-20 2006-08-01 Clariant Finance (Bvi) Limited Mixture of phosphanes and chromane derivatives
AU2001293318A1 (en) * 2000-09-01 2002-03-13 Sasol Technology (Pty) Ltd. Carbonylation catalyst
DE10241814A1 (de) * 2002-09-06 2004-03-25 Covion Organic Semiconductors Gmbh Prozeß zur Herstellung von Aryl-Aryl gekoppelten Verbindungen
CN100366343C (zh) * 2005-10-13 2008-02-06 重庆西南合成制药有限公司 一种有机铑催化剂及应用
EP2149570A1 (en) * 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Process for the manufacture of epichlorohydrin using hydrogen peroxide and a manganese komplex
EP2149569A1 (en) * 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Process for the manufacture of a 1,2-Epoxide
EP2179980A1 (en) * 2008-10-23 2010-04-28 Cognis IP Management GmbH Process for the manufacture of saturated mono- or polycyclic compounds
EP2343288A1 (en) 2009-11-27 2011-07-13 Momentive Specialty Chemicals Research Belgium S.A. Process for the manufacture of propylene oxide
EP2357180A1 (en) 2010-02-02 2011-08-17 Momentive Specialty Chemicals Research Belgium S.A. Manufacture of epoxyethyl ethers or glycidyl ethers
EP2354130A1 (en) 2010-02-02 2011-08-10 Momentive Specialty Chemicals Research Belgium Manufacture of an epoxyethyl carboxylate or glycidyl carboxylate
EP2354129A1 (en) 2010-02-02 2011-08-10 Momentive Specialty Chemicals Research Belgium S.A. Epoxidation process
EP2354131A1 (en) * 2010-02-02 2011-08-10 Momentive Specialty Chemicals Research Belgium Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
DE102010043558A1 (de) * 2010-11-08 2012-05-10 Evonik Oxeno Gmbh Verfahren zur Hydroformylierung von ungesättigten Verbindungen
EP2537836A1 (en) 2011-06-22 2012-12-26 Momentive Specialty Chemicals Research Belgium S.A. Apparatus and methods to preserve catalyst activity in an epoxidation process
CN102351912B (zh) * 2011-10-25 2014-11-05 中国海洋石油总公司 一种三[三（3-磺酸钠基苯基）膦]羰基氢化铑的制法
CN102391313A (zh) * 2011-10-25 2012-03-28 中国海洋石油总公司 一种二[三（3-磺酸钠基苯基）膦]氯羰基铑的制法
CN102351913B (zh) * 2011-10-25 2014-09-17 中国海洋石油总公司 一种三[三（3-磺酸钠基苯基）膦]氯化铑的制备方法
AU2012348569B2 (en) 2011-12-06 2016-09-01 University Of Johannesburg Use of silver (I) complexes as anticancer agents
CN105618145B (zh) * 2014-11-07 2017-11-07 中国石油天然气股份有限公司 一种三[三(间‑磺酸钠苯基)膦]氯化铑催化剂的制备方法
JP7380233B2 (ja) * 2020-01-14 2023-11-15 株式会社豊田中央研究所 二酸化炭素還元触媒
CN116586119A (zh) * 2023-02-28 2023-08-15 南京大学 一种金基团簇催化剂及其制备方法和应用

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE129779C (ko) *
GB1095146A (en) * 1964-05-15 1967-12-13 Brian Lewis Booth Co-ordination compounds of manganese
US4248802A (en) 1975-06-20 1981-02-03 Rhone-Poulenc Industries Catalytic hydroformylation of olefins
FR2338253A1 (fr) 1976-01-13 1977-08-12 Rhone Poulenc Ind Procede d'hydrocyanation de composes organiques insatures comportant au moins une double liaison ethylenique
US4120901A (en) * 1977-08-31 1978-10-17 Monsanto Company Production of primary and secondary amines by reaction of ammonia with conjugated diene in the presence of Pd/phosphine catalyst and primary or secondary aliphatic alcohol solvent medium
US4336148A (en) * 1977-09-07 1982-06-22 Ciba-Geigy Corporation Complex compound, process for their preparation, and their use
CA1176661A (en) * 1980-04-28 1984-10-23 David M. Gardner Preparation of amines from olefins using certain transition metal catalysts
US4454321A (en) * 1980-04-28 1984-06-12 Pennwalt Corporation Preparation of amines from olefins using certain transition metal catalysts
US4442290A (en) * 1981-06-12 1984-04-10 Polaroid Corporation Development restrainer release compounds
PT76061A (en) * 1982-12-30 1983-01-01 Stable homogeneous hydrogenation rhodium catalyst - useful in high yield prodn. of doxycycline by stereospecific hydrogenation
US4522932A (en) * 1982-09-27 1985-06-11 Exxon Research & Engineering Co. Phosphine and phosphonium compounds and catalysts
FR2550202B1 (fr) * 1983-08-03 1986-03-21 Rhone Poulenc Rech Procede de preparation de tri(m-sulfophenyl) phosphine
US4625069A (en) * 1983-10-12 1986-11-25 Minnesota Mining And Manufacturing Fluorochemical rhodium compounds
FR2571725B1 (fr) * 1984-10-16 1987-09-18 Rhone Poulenc Chim Base Complexes rhodies, dinucleaires et hydrosolubles et leur utilisation comme catalyseur d'hydroformylation
DE3616057A1 (de) * 1986-05-13 1987-11-19 Ruhrchemie Ag Verfahren zur herstellung von aldehyden
US4822915A (en) * 1986-07-21 1989-04-18 Union Carbide Corporation Phosphine and sulfonate bearing ligands
US4689437A (en) * 1986-07-21 1987-08-25 Union Carbide Corporation Oligomerization to alpha-olefins
DE3822036A1 (de) 1988-06-30 1990-02-08 Hoechst Ag Verfahren zur trennung von in waessriger oder waessrig/organischer loesung enthaltenen substanzgemischen

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