CA1312094C - Transition metal complex catalyzed reactions - Google Patents

Transition metal complex catalyzed reactions

Info

Publication number
CA1312094C
CA1312094C CA000537549A CA537549A CA1312094C CA 1312094 C CA1312094 C CA 1312094C CA 000537549 A CA000537549 A CA 000537549A CA 537549 A CA537549 A CA 537549A CA 1312094 C CA1312094 C CA 1312094C
Authority
CA
Canada
Prior art keywords
rhodium
hydroformylation
organic polymer
aldehyde
phosphite
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.)
Expired - Lifetime
Application number
CA000537549A
Other languages
English (en)
French (fr)
Inventor
David Robert Bryant
John Michael Maher
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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
Priority claimed from US06/865,061 external-priority patent/US4717775A/en
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Application granted granted Critical
Publication of CA1312094C publication Critical patent/CA1312094C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
CA000537549A 1986-05-20 1987-05-20 Transition metal complex catalyzed reactions Expired - Lifetime CA1312094C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US06/865,061 US4717775A (en) 1984-12-28 1986-05-20 Transition metal complex catalyzed reactions
US865,061 1986-05-20
US046,821 1987-05-11
US07/046,821 US4774361A (en) 1986-05-20 1987-05-11 Transition metal complex catalyzed reactions

Publications (1)

Publication Number Publication Date
CA1312094C true CA1312094C (en) 1992-12-29

Family

ID=26724327

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000537549A Expired - Lifetime CA1312094C (en) 1986-05-20 1987-05-20 Transition metal complex catalyzed reactions

Country Status (12)

Country Link
US (1) US4774361A (en:Method)
EP (1) EP0276231B1 (en:Method)
JP (1) JPS63503385A (en:Method)
CN (1) CN1010011B (en:Method)
AU (1) AU613312B2 (en:Method)
CA (1) CA1312094C (en:Method)
DE (1) DE3773890D1 (en:Method)
ES (1) ES2004935A6 (en:Method)
IN (1) IN169727B (en:Method)
MX (1) MX166107B (en:Method)
NO (1) NO166583C (en:Method)
WO (1) WO1987007261A2 (en:Method)

Families Citing this family (85)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4835299A (en) * 1987-03-31 1989-05-30 Union Carbide Corporation Process for purifying tertiary organophosphites
IT1237530B (it) * 1989-12-12 1993-06-08 Eniricerche Spa Procedimento per la sintesi diretta di alcoli da olefine,ossidi di carbonio e idrogeno,promossa da un catalizzatore di rodio supportato
US5210318A (en) * 1990-05-04 1993-05-11 Union Carbide Chemicals & Plastics Technology Corporation Catalysts and processes useful in producing 1,3-diols and/or 3-hydroxyldehydes
US5087763A (en) * 1990-11-09 1992-02-11 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process
JP2946790B2 (ja) * 1991-03-14 1999-09-06 三菱化学株式会社 アルデヒド類の製造法
US5360938A (en) * 1991-08-21 1994-11-01 Union Carbide Chemicals & Plastics Technology Corporation Asymmetric syntheses
GB9119955D0 (en) * 1991-09-18 1991-10-30 Imperial College Treatment of aqueous supplies containing organic material
US5243099A (en) * 1991-12-06 1993-09-07 Union Carbide Chemicals & Plastics Technology Corporation Synthesis of alpha-substituted alkadienes
US5169981A (en) * 1991-12-06 1992-12-08 Union Carbide Chemicals & Plastics Technology Corporation Synthesis of alpha-substituted alkadienes
US5756855A (en) 1994-08-19 1998-05-26 Union Carbide Chemicals & Plastics Technology Corporation Stabilization of phosphite ligands in hydroformylation process
US5672766A (en) * 1994-12-12 1997-09-30 Mitsubishi Chemical Corporation Method for producing aldehydes
KR970703805A (ko) * 1995-05-01 1997-08-09 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 막 분리방법(Membrane Separation)
US5739352A (en) * 1995-10-19 1998-04-14 United Carbide Chemicals & Plastics Technology Corporation Process for preparing carboxylic acids
DE19605435A1 (de) * 1996-02-14 1997-08-21 Basf Ag Verfahren zur Herstellung von Aldehyden durch Hydroformylierung mit einem Rhodiumkatalysator und Wiedergewinnung des Rhodiumkatalysators durch Extraktion
US6090987A (en) * 1998-07-06 2000-07-18 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
CN1163463C (zh) * 1998-12-10 2004-08-25 三菱化学株式会社 醛的制备方法
JP3921853B2 (ja) * 1998-12-10 2007-05-30 三菱化学株式会社 アルデヒド類及びアルコール類の製造方法
GB9918229D0 (en) † 1999-08-04 1999-10-06 Ici Plc Improvements relating to metal-compound catalysed processes
DE19954510A1 (de) 1999-11-12 2001-05-17 Oxeno Olefinchemie Gmbh Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen
EP1168111A3 (en) 2000-06-27 2009-06-03 Dai Nippon Printing Co., Ltd. Multilayer volume hologram, and label for multilayer volume hologram fabrication
EP1249441A1 (en) 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process
DE10220801A1 (de) * 2002-05-10 2003-11-20 Oxeno Olefinchemie Gmbh Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste
PL206922B1 (pl) * 2002-08-31 2010-10-29 Oxeno Olefinchemie Gmbh Sposób katalitycznego hydroformylowania związków nienasyconych olefinowo
JP4523411B2 (ja) * 2002-08-31 2010-08-11 エボニック オクセノ ゲゼルシャフト ミット ベシュレンクテル ハフツング 環状炭酸エステルの存在下でのオレフィン性不飽和化合物、特にオレフィンのヒドロホルミル化法
ATE470736T1 (de) * 2003-01-16 2010-06-15 Teijin Fibers Ltd Differential-shrinkage-filamentgarn in kombination mit polyester
EP2308817B1 (en) 2003-07-03 2016-10-05 Dow Technology Investments LLC Minimization of ligand degradation products, or reversion of same to useful phosphine ligands
DE10349343A1 (de) * 2003-10-23 2005-06-02 Basf Ag Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden
EP1776328B2 (en) 2004-08-02 2025-03-26 Dow Technology Investments LLC Stabilization of a hydroformylation process
CN101657407B (zh) * 2007-03-20 2014-02-12 陶氏技术投资有限公司 改善对产物同分异构体的控制的加氢甲酰基化方法
WO2008123740A1 (en) * 2007-04-09 2008-10-16 Lg Chem, Ltd. Catalyst composition including phosphite ligands and hydroformylation method using the same
MY155290A (en) 2008-07-03 2015-09-30 Basf Se Process of controlling heavies in a recycle catalyst stream
MX2011005103A (es) 2008-11-14 2011-08-04 Univ Kansas Complejos de catalizador de metal de transicion soportados en polimeros y metodos de uso.
EP2414314B1 (en) 2009-03-31 2017-09-13 Dow Technology Investments LLC Hydroformylation process with triphenylphosphine and a doubly open-ended bisphosphite ligand
US7928267B1 (en) * 2009-06-22 2011-04-19 Eastman Chemical Company Phosphite containing catalysts for hydroformylation processes
JP5823967B2 (ja) 2009-10-16 2015-11-25 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー 気相ヒドロホルミル化方法
EP2516373B2 (en) 2009-12-22 2020-08-12 Dow Technology Investments LLC Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process
US8664451B2 (en) 2009-12-22 2014-03-04 Dow Technology Investments Llc Controlling the normal:ISO aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure
KR101918054B1 (ko) 2009-12-22 2018-11-13 다우 테크놀로지 인베스트먼츠 엘엘씨. 합성 기체 분압의 조절에 의한 혼합된 리간드 하이드로폼일화 공정에서의 노말:아이소 알데하이드 비의 조절 방법
CN103153462B (zh) 2010-10-05 2016-06-01 陶氏技术投资有限责任公司 加氢甲酰基化方法
SG190138A1 (en) 2010-11-12 2013-06-28 Dow Technology Investments Llc Mitigation of fouling in hydroformylation processes by water addition
SA112330271B1 (ar) 2011-04-18 2015-02-09 داو تكنولوجى انفستمنتس ال ال سى تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء
KR20140143382A (ko) 2012-03-07 2014-12-16 바스프 에스이 Ｃ3-ｃ20-알데히드의 수소화 및 증류에서의 열 집적 방법
KR102104824B1 (ko) 2012-04-12 2020-04-28 바스프 에스이 연속적 히드로포르밀화에서 촉매를 보충하는 방법
US8889917B2 (en) 2012-04-12 2014-11-18 Basf Se Method of supplementing the catalyst in continuous hydroformylation
EP2855016A1 (en) 2012-06-04 2015-04-08 Dow Technology Investments LLC Hydroformylation process
KR102131204B1 (ko) * 2012-08-29 2020-07-07 다우 테크놀로지 인베스트먼츠 엘엘씨. 촉매 제조 방법
WO2014051975A1 (en) 2012-09-25 2014-04-03 Dow Technology Investments Llc Process for stabilizing a phosphite ligand against degradation
EP2740535A1 (en) 2012-12-04 2014-06-11 Dow Technology Investments LLC Bidentate ligands for hydroformylation of ethylene
JP6174711B2 (ja) 2012-12-06 2017-08-02 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化方法
CN104045532B (zh) 2013-03-15 2018-05-25 陶氏技术投资有限责任公司 加氢甲酰化方法
CN104725170B (zh) 2013-12-19 2019-08-23 陶氏技术投资有限责任公司 加氢甲酰化方法
WO2015094781A1 (en) 2013-12-19 2015-06-25 Dow Technology Investments Llc Hydroformylation process
EP3126319B1 (en) 2014-03-31 2019-07-17 Dow Technology Investments LLC Hydroformylation process
US10501486B2 (en) 2014-05-14 2019-12-10 Dow Technology Investments Llc Stabilized organophosphorous compounds
MY184826A (en) 2014-12-04 2021-04-24 Dow Technology Investments Llc Hydroformylation process
TWI709566B (zh) 2015-09-30 2020-11-11 美商陶氏科技投資公司 用於製造有機磷化合物的方法
TWI709568B (zh) 2015-09-30 2020-11-11 美商陶氏科技投資公司 用於製造有機磷化合物的方法
MY189779A (en) 2015-11-10 2022-03-07 Dow Technology Investments Llc Process for producing aldehydes
JP6885963B2 (ja) 2016-02-11 2021-06-16 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー オレフィンを、アルコール、エーテル、またはそれらの組み合わせに転化するためのプロセス
US10407372B2 (en) 2016-03-18 2019-09-10 Dow Technology Investments Llc Hydroformylation process
TW201840362A (zh) 2016-11-08 2018-11-16 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
TW201840363A (zh) 2016-11-08 2018-11-16 美商陶氏科技投資有限公司 處理氫甲醯化催化劑溶液之方法
TWI758353B (zh) 2016-11-08 2022-03-21 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
RU2020115090A (ru) 2017-10-25 2021-10-29 Дау Текнолоджи Инвестментс Ллк Способ уменьшения образования тяжелых фракций в растворе, содержащем альдегидные соединения, образованные в процессе гидроформилирования
WO2019094290A1 (en) 2017-11-13 2019-05-16 Dow Technology Investments Llc Processes for recovery of rhodium from a hydroformylation process
TWI793216B (zh) 2017-12-07 2023-02-21 美商陶氏科技投資公司 氫甲醯化方法
CA3100779A1 (en) 2018-05-30 2019-12-05 Dow Technology Investments Llc Methods of controlling hydroformylation processes
CN112055614A (zh) 2018-05-30 2020-12-08 陶氏技术投资有限责任公司 包括单膦、四膦配位体的组合的催化剂组合物和使用其的加氢甲酰化过程
CA3100778A1 (en) 2018-05-30 2019-12-05 Dow Technology Investments Llc Methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in hydroformylation processes
CN113179638B (zh) * 2018-11-29 2023-11-28 陶氏技术投资有限责任公司 加氢甲酰化工艺
US20220143590A1 (en) * 2019-06-27 2022-05-12 Dow Technology Investments Llc Process to prepare solution from hydroformylation process for precious metal recovery
TWI874467B (zh) 2019-11-05 2025-03-01 美商陶氏科技投資有限公司 用於自ｃ６或更高碳數烯烴氫甲醯化製程之催化劑淨化流回收銠之方法
CN114929660A (zh) 2019-12-19 2022-08-19 陶氏技术投资有限责任公司 用于制备异戊二烯和包含至少六个碳原子的单烯烃的方法
CN114478214B (zh) * 2020-10-23 2024-05-17 中国石油化工股份有限公司 一种氢甲酰化方法和一种氢甲酰化产物的分离方法
KR20230120131A (ko) 2020-12-14 2023-08-16 다우 테크놀로지 인베스트먼츠 엘엘씨. 히드로포르밀화 공정에서 촉매 금속 책임량을 개선시키는 방법
CN118103532A (zh) 2021-11-11 2024-05-28 陶氏技术投资有限责任公司 用于从加氢甲酰化过程中回收铑的方法
JP2024545133A (ja) 2021-12-16 2024-12-05 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー 化合物、そのような化合物を含む遷移金属錯体ヒドロホルミル化触媒前駆体組成物、及びヒドロホルミル化プロセス
CN118338965A (zh) 2021-12-16 2024-07-12 陶氏技术投资有限责任公司 包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法
WO2024129290A1 (en) 2022-12-13 2024-06-20 Dow Technology Investments Llc Process to minimize polyphosphine usage by making use of degradation products
WO2024228768A1 (en) 2023-05-04 2024-11-07 Dow Technology Investments Llc Hydroformylation process
GB202307175D0 (en) 2023-05-15 2023-06-28 Johnson Matthey Davy Technologies Ltd Process for hydrogenating a substrate
WO2025006020A1 (en) 2023-06-26 2025-01-02 Dow Technology Investments Llc Methods of controlling hydroformylation processes
WO2025029349A1 (en) 2023-08-03 2025-02-06 Dow Technology Investments Llc Hydroformylation process
WO2025029369A1 (en) 2023-08-03 2025-02-06 Dow Technology Investments Llc Process for improving rhodium/phosphite- based homogenous hydroformylation catalyst activity
GB202404300D0 (en) 2024-03-26 2024-05-08 Johnson Matthey Davy Technologies Ltd Process for the production of 2-alkylalkanol

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE156528C (en:Method) *
US4482748A (en) * 1967-05-29 1984-11-13 Celanese Corporation Hydrocarbonylation
DE2145532C3 (de) * 1971-09-11 1975-02-20 Basf Ag, 6700 Ludwigshafen Verfahren zur Aufarbeitung von Hydroformylierungsgemischen
DE2326489A1 (de) * 1973-05-24 1974-12-12 Ernst Prof Dr Bayer Verfahren zur katalyse unter verwendung von loeslichen metallverbindungen synthetischer polymerer
JPS5638576B2 (en:Method) * 1974-07-25 1981-09-08
US4148830A (en) * 1975-03-07 1979-04-10 Union Carbide Corporation Hydroformylation of olefins
JPS6022688B2 (ja) * 1976-12-29 1985-06-03 和光純薬工業株式会社 アルデヒド化合物の蒸留方法
DE2966350D1 (en) * 1978-08-17 1983-12-01 Heyl Chem Pharm Polymeric hydrogenation catalysts, process for preparing these catalysts and their use for catalytic hydrogenations
US4235744A (en) * 1978-10-30 1980-11-25 Standard Oil Company (Ohio) Carbonylation of olefinically unsaturated compounds
US4504684A (en) * 1982-01-06 1985-03-12 The Standard Oil Company Metal coordination polymers as hydroformylation and hydrogenation catalysts
DE3372361D1 (en) * 1982-06-11 1987-08-13 Davy Mckee London Hydroformylation process
US4528403A (en) * 1982-10-21 1985-07-09 Mitsubishi Chemical Industries Ltd. Hydroformylation process for preparation of aldehydes and alcohols
US4528404A (en) * 1983-03-16 1985-07-09 Exxon Research And Engineering Co. High temperature hydroformylation in the presence of triarylphosphine rhodium carbonyl hydride complex catalyst systems
GB8334359D0 (en) * 1983-12-23 1984-02-01 Davy Mckee Ltd Process
US4599206A (en) * 1984-02-17 1986-07-08 Union Carbide Corporation Transition metal complex catalyzed reactions
US4599456A (en) * 1984-12-20 1986-07-08 Phillips Petroleum Company Novel aldehyde-phosphine compositions and uses therefor
US4668651A (en) * 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
US4613701A (en) * 1985-09-19 1986-09-23 Celanese Corporation Recovery of rhodium from hydroformylation reaction product

Also Published As

Publication number Publication date
WO1987007261A2 (en) 1987-12-03
CN87104311A (zh) 1988-06-08
JPS63503385A (ja) 1988-12-08
MX166107B (es) 1992-12-21
EP0276231A1 (en) 1988-08-03
NO166583B (no) 1991-05-06
IN169727B (en:Method) 1991-12-14
JPH0548215B2 (en:Method) 1993-07-20
CN1010011B (zh) 1990-10-17
NO880207L (no) 1988-01-19
DE3773890D1 (de) 1991-11-21
WO1987007261A3 (en) 1988-04-07
NO166583C (no) 1991-08-14
AU7489887A (en) 1987-12-22
EP0276231B1 (en) 1991-10-16
US4774361A (en) 1988-09-27
AU613312B2 (en) 1991-08-01
NO880207D0 (no) 1988-01-19
ES2004935A6 (es) 1989-02-16

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