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

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 (OSRAM)
EP (1) EP0276231B1 (OSRAM)
JP (1) JPS63503385A (OSRAM)
CN (1) CN1010011B (OSRAM)
AU (1) AU613312B2 (OSRAM)
CA (1) CA1312094C (OSRAM)
DE (1) DE3773890D1 (OSRAM)
ES (1) ES2004935A6 (OSRAM)
IN (1) IN169727B (OSRAM)
MX (1) MX166107B (OSRAM)
NO (1) NO166583C (OSRAM)
WO (1) WO1987007261A2 (OSRAM)

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
DE69916560T2 (de) * 1998-12-10 2005-04-14 Mitsubishi Chemical Corp. Verfahren zur Herstellung von Aldehyden
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
EP2453320B1 (en) 2000-06-27 2016-06-29 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
MXPA05002283A (es) * 2002-08-31 2005-06-08 Oxeno Olefinchemie Gmbh Procedimiento para la hidroformilacion de compuestos olefinicamente insaturados, en particular olefinas, en presencia de esteres de acido carbonico ciclicos.
JP2005537330A (ja) * 2002-08-31 2005-12-08 オクセノ　オレフィンヒェミー　ゲゼルシャフト　ミット　ベシュレンクテル　ハフツング 環状カルボン酸エステルの存在で非変性金属錯体により触媒活性されるオレフィン不飽和化合物のヒドロホルミル化によりアルデヒドを製造する方法
CA2513348A1 (en) * 2003-01-16 2004-07-29 Teijin Fibers Limited Differential-shrinkage polyester combined filament yarn
CA2530739C (en) 2003-07-03 2012-09-25 Union Carbide Chemicals & Plastics Technology Corporation 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
RU2388742C2 (ru) 2004-08-02 2010-05-10 Дау Текнолоджи Инвестментс Ллс. Стабилизация процесса гидроформилирования
JP5400627B2 (ja) * 2007-03-20 2014-01-29 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 生成物異性体の制御が改善されたヒドロホルミル化方法
KR100964098B1 (ko) * 2007-04-09 2010-06-16 주식회사 엘지화학 포스파이트 리간드를 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법
EP2703380B1 (en) 2008-07-03 2015-11-04 Dow Technology Investments LLC Process for working up a hydroformylation output
JP5670909B2 (ja) 2008-11-14 2015-02-18 ユニバーシティ・オブ・カンザス ポリマーに担持された遷移金属触媒錯体、及びその使用方法
MX2011010379A (es) 2009-03-31 2011-10-17 Dow Technology Investments Llc Proceso de hidroformilacion con un ligando de biosfosfito doblemente de extremo abierto.
US7928267B1 (en) * 2009-06-22 2011-04-19 Eastman Chemical Company Phosphite containing catalysts for hydroformylation processes
CN107266298A (zh) 2009-10-16 2017-10-20 陶氏技术投资有限责任公司 气相加氢甲酰化方法
CN103951550B (zh) 2009-12-22 2016-06-01 陶氏技术投资有限责任公司 通过控制烯烃分压来控制混合配体加氢甲酰化工艺中的正构:异构醛比率
PL2942343T3 (pl) 2009-12-22 2020-02-28 Dow Technology Investments Llc Kontrolowanie stosunku aldehydu normalnego : aldehydu izo w procesie hydroformylowania z ligandami mieszanymi
US8598389B2 (en) 2009-12-22 2013-12-03 Dow Technology Investments Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the syngas partial pressure
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
MY170250A (en) 2010-11-12 2019-07-13 Basf Se 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
MY185096A (en) 2012-03-07 2021-04-30 Basf Se Method for thermal integration in the hydrogenation and distillation of c3-c20 aldehydes
US8889917B2 (en) 2012-04-12 2014-11-18 Basf Se Method of supplementing the catalyst in continuous hydroformylation
SG11201405863QA (en) 2012-04-12 2014-11-27 Basf Se Method for replenishing the catalyst in continuous hydroformylation
JP6329136B2 (ja) 2012-06-04 2018-05-23 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 ヒドロホルミル化プロセス
JP6339572B2 (ja) * 2012-08-29 2018-06-06 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 触媒製造方法
BR112015006495B1 (pt) 2012-09-25 2020-12-15 Dow Technology Investments Llc Processo para estabilizar um ligante de fosfito contra degradação num fluido de reação de hidroformilação
EP2740535A1 (en) 2012-12-04 2014-06-11 Dow Technology Investments LLC Bidentate ligands for hydroformylation of ethylene
KR102098429B1 (ko) 2012-12-06 2020-04-07 다우 테크놀로지 인베스트먼츠 엘엘씨. 하이드로포밀화 방법
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
JP2016540780A (ja) 2013-12-19 2016-12-28 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 ヒドロホルミル化プロセス
EP3126319B1 (en) 2014-03-31 2019-07-17 Dow Technology Investments LLC Hydroformylation process
WO2015175158A1 (en) 2014-05-14 2015-11-19 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
CA3004907C (en) 2015-11-10 2024-01-02 Dow Technology Investments Llc Process for producing aldehydes
BR112018016320B1 (pt) 2016-02-11 2022-07-12 Dow Technology Investments Llc Processo para converter olefinas em álcoois, éteres ou combinações dos mesmos
JP6889179B2 (ja) 2016-03-18 2021-06-18 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 ヒドロホルミル化プロセス
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
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
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
CN111212826B (zh) 2017-10-25 2023-05-23 陶氏技术投资有限责任公司 减少在加氢甲酰化过程中形成的包含醛化合物的溶液中重物质形成的方法
EP3710161B1 (en) 2017-11-13 2024-10-16 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
MX2020011383A (es) 2018-05-30 2020-11-24 Dow Technology Investments Llc Composiciones catalizadoras que comprenden la combinacion de una monofosfina, un ligando de tetrafosfina y proceso de hidroformilacion que lo usa.
CN112088153A (zh) 2018-05-30 2020-12-15 陶氏技术投资有限责任公司 控制加氢甲酰化过程的方法
KR20250057144A (ko) 2018-05-30 2025-04-28 다우 테크놀로지 인베스트먼츠 엘엘씨. 하이드로포밀화 공정에서 촉매의 탈활성화를 느리게 하고/하거나 테트라포스핀 리간드 사용을 느리게 하는 방법
KR102841371B1 (ko) 2018-11-29 2025-08-01 다우 테크놀로지 인베스트먼츠 엘엘씨. 히드로포르밀화 공정
JP7547397B2 (ja) * 2019-06-27 2024-09-09 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 貴金属回収のためのヒドロホルミル化プロセスから溶液を調製するプロセス
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
CN116635362A (zh) 2020-12-14 2023-08-22 陶氏技术投资有限责任公司 改进加氢甲酰化方法中的催化金属可计量性的方法
EP4430218A1 (en) 2021-11-11 2024-09-18 Dow Technology Investments LLC Processes for recovering rhodium from hydroformylation processes
WO2023114579A1 (en) 2021-12-16 2023-06-22 Dow Technology Investments Llc Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes
WO2023114578A1 (en) 2021-12-16 2023-06-22 Dow Technology Investments Llc Transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes
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 (OSRAM) *
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 (OSRAM) * 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
EP0008407B1 (de) * 1978-08-17 1983-10-26 Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG Polymere Hydrierkatalysatoren, Verfahren zur Herstellung dieser Katalysatoren und ihre Verwendung für katalytische Hydrierungen
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
AU7489887A (en) 1987-12-22
US4774361A (en) 1988-09-27
EP0276231A1 (en) 1988-08-03
EP0276231B1 (en) 1991-10-16
CN1010011B (zh) 1990-10-17
WO1987007261A2 (en) 1987-12-03
JPS63503385A (ja) 1988-12-08
ES2004935A6 (es) 1989-02-16
NO166583B (no) 1991-05-06
JPH0548215B2 (OSRAM) 1993-07-20
CN87104311A (zh) 1988-06-08
NO880207L (no) 1988-01-19
IN169727B (OSRAM) 1991-12-14
NO166583C (no) 1991-08-14
NO880207D0 (no) 1988-01-19
MX166107B (es) 1992-12-21
AU613312B2 (en) 1991-08-01
DE3773890D1 (de) 1991-11-21
WO1987007261A3 (en) 1988-04-07

Similar Documents

Publication Publication Date Title
CA1312094C (en) Transition metal complex catalyzed reactions
EP1144114B1 (en) Improved metal-ligand complex catalyzed processes
CA2230561C (en) Improved metal-ligand complex catalyzed processes
CA2239618C (en) Improved metal-ligand complex catalyzed processes
CN111344274B (zh) 氢甲酰化方法
CN104955568A (zh) 用于稳定亚磷酸酯配体抵抗降解的方法
AU719941B2 (en) Improved metal-ligand complex catalyzed processes
CN104837800B (zh) 氢甲酰化方法
KR910007047B1 (ko) 개선된 전이금속 착물 촉매화 반응
RU2777364C2 (ru) Способ гидроформилирования
WO2025029369A1 (en) Process for improving rhodium/phosphite- based homogenous hydroformylation catalyst activity
BR112020009739B1 (pt) Processo de hidroformilação para produzir um aldeído
PL149758B1 (pl) Sposób wytwarzania aldehydów przez hydroformylowanie 0lefin0w0 nienasyconych związków
MXPA01000031A (en) Improved metal-ligand complex catalyzed processes

Legal Events

Date Code Title Description
MKLA Lapsed