KR940006983A - 하이드로포밀화 방법 - Google Patents

하이드로포밀화 방법 Download PDF

Info

Publication number
KR940006983A
KR940006983A KR1019930020125A KR930020125A KR940006983A KR 940006983 A KR940006983 A KR 940006983A KR 1019930020125 A KR1019930020125 A KR 1019930020125A KR 930020125 A KR930020125 A KR 930020125A KR 940006983 A KR940006983 A KR 940006983A
Authority
KR
South Korea
Prior art keywords
independently
group
radicals
bis
ligand
Prior art date
Application number
KR1019930020125A
Other languages
English (en)
Other versions
KR100198688B1 (ko
Inventor
마이클 마허 존
에드워드 바빈 제임스
언스트빌리그
로버트 브라이언트 데이비드
와이 롱 타크
Original Assignee
카렌 엘. 존슨
유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션
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
Application filed by 카렌 엘. 존슨, 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 filed Critical 카렌 엘. 존슨
Publication of KR940006983A publication Critical patent/KR940006983A/ko
Application granted granted Critical
Publication of KR100198688B1 publication Critical patent/KR100198688B1/ko

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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07F15/0073—Rhodium compounds
    • C07F15/008—Rhodium compounds without a metal-carbon linkage
    • 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
    • B01J31/18—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
    • B01J31/1845—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 phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • 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
    • C07C47/00—Compounds having —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/822—Rhodium
    • 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)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Lubricants (AREA)

Abstract

부가수, 약산성 화합물 및 부가수와 약산성 화합물 둘다로 이루어진 그룹 중에서 선택된 촉매 활성 증강제의 존재하에서 수행함을 특징으로 하는 개선된 로듐-오가노 포스파이트 착물-촉매화된 하이드로포밀화 방법에 대해 기술하였다.

Description

하이드로포밀화 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 올레핀계 불포화 화합물을, 비스포스파이트 리간드가 하기 일반식(Ⅰ)및 (Ⅱ)의 리간드로 이루어진 그룹중에서 선택된 리간드인 가용화된 로듐-비스포스파이트 착물 촉매의 존재하에 하이드로포밀화 반응매질중에 존재하는, 부가수, pka치가 약 1.0내지 약 12인 약산성 화합물 및 부가수와 pka치가 약 1.0내지 약 12인 약산성 화합물 둘다로 이루어진 그룹중에서 선택된 소량의 촉매 활성 증강제의 존재하에 일산화탄소 및 수소와 반응시킴을 특징으로 하는, 알데하이드를 제조하기 위한 연속식 하이드로포밀화 방법.
    상기식에서, X1및 X2는 각각 개별적으로 수소, 메틸, 에틸 및 n-프로필로 이루어진 그룹중에서 선택된 래디칼이고, Z1및 Z2는 각각 개별적으로 수소 또는 탄소수 1 내지 18의 치환체 래디칼이며, X는 각각 알킬렌, 알킬렌-옥시-알킬렌, 아릴렌 및 아릴렌-(Q)n-아릴렌〔여기서, 알킬렌 래디칼은 동일하거나 상이하며 각각 개별적으로 탄소수가 2내지 18이고, 아릴렌 래디칼은 동일하거나 상이하며 가각 개별적으로 탄소수가 6내지 18이고, Q는 각각 개별적으로 -CR5R6-2가 브릿지 그룹(여기서, R5및 R6래디칼은 각각 개별적으로 수소 또는 메틸 래디칼이다)이며, n은 각각 개별적으로 0또는 1이다〕으로 이루어진 그룹 중에서 선택된 2가 래디칼이다.
  2. 제1항에 있어서, 사용된 촉매 활성 증강제의 소량이 하이드로포밀화 반응 매질의 총중량을 기준으로 하여 약 0.05내지 약 20중량％ 범위일 수 있는 방법.
  3. 제2항에 있어서, 약산성 화합물이 2.2'-디하이드록시 비페닐인 방법.
  4. 제2항에 있어서, 상기한 임의의 약산성 화합물 부가제의 부재하에서 수행하는 방법.
  5. 제2항에 있어서, 사용된 비스포스파이트 리간드가 일반식(Ⅴ) 및 (Ⅵ)으로 이루어진 그룹중에서 선택된 리간드인 방법.
    상기식에서 Z1,Z2,R3및 R4는 각각 개별적으로 수소, 탄소수 1내지 8의 알킬 래디칼, 페닐, 벤질, 사이크로헥실, 및 1-메틸사이클로헥실, 하이드록시 및 탄소수 1내지 8의 알콕시 래디칼 중에서 선택된 래디칼이고, R1및 R2는 각각 개별적으로 탄소수 3내지 8의 측쇄 알킬 래디칼, 사이클로헥실 및 1-메틸사이클로헥실로 이루어진 그룹중에서 선택된 래디칼이며, X1,X2,Q 및 n은 제1항에서 정의한 바와 같다.
  6. 제2항에 있어서, 에폭사이드 화합물이 또한 하이드로포밀화 반응 매질중에 존재하는 방법.
  7. 제4항에 있어서, 비스포스파이트 리간드가 6,6'[[3,3', 5,5-테트라키스(1,1-디메틸에틸)1,1'-비페닐-2,2'-디일]비스(옥시)비스-디벤조[d,f][1,3,2]-디옥사포스페핀인 방법.
  8. 제4항에 있어서, 비스포스파이트 리간드가 6,6'[[3,3', 5,5-테트라키스(1,1-디메틸프로필)1,1'-비페닐-2,2'-디일]비스(옥시)비스-디벤조[d,f][1,3,2]-디옥사포스페핀인 방법.
  9. 제4항에 있어서, 비스포스파이트 리간드가 6,6'[[3,3', 비스(1,1-디메틸에틸)5,5'-디메톡시[1,1-비페닐]-2,2'-디일]비스(옥시)비스-디벤조[d,f][1,3,2]-디옥사포스페핀인 방법.
  10. 제4항에 있어서, 사용된 비스포스파이트 리간드가 일반식(Ⅴ) 및 (Ⅵ)으로 이루어진 그룹중에서 선택된 리간드인 방법.
    상기식에서 Z1,Z2,R3및 R4는 각각 개별적으로 수소, 탄소수 1내지 8의 알킬 래디칼, 페닐, 벤질, 사이클로헥실, 및 1-메틸사이클로헥실, 하이드록시 및 탄소수 1내지 8의 알콕시 래디칼 중에서 선택된 래디칼이고, R1및 R2는 각각 개별적으로 탄소수 3내지 8의 측쇄 알킬 래디칼, 사이클로헥실 및 1-메틸사이클로헥실로 이루어진 그룹중에서 선택된 래디칼이며, X1,X2,Q 및 n은 제1항에서 정의한 바와 같다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930020125A 1992-09-29 1993-09-28 하이드로포밀화 방법 KR100198688B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/953,016 US5288918A (en) 1992-09-29 1992-09-29 Hydroformylation process
US7/953,016 1992-09-29

Publications (2)

Publication Number Publication Date
KR940006983A true KR940006983A (ko) 1994-04-26
KR100198688B1 KR100198688B1 (ko) 1999-06-15

Family

ID=25493467

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930020125A KR100198688B1 (ko) 1992-09-29 1993-09-28 하이드로포밀화 방법

Country Status (16)

Country Link
US (1) US5288918A (ko)
EP (1) EP0590613B1 (ko)
JP (1) JP2942693B2 (ko)
KR (1) KR100198688B1 (ko)
CN (1) CN1056364C (ko)
AU (1) AU4864393A (ko)
BR (1) BR9303934A (ko)
CA (1) CA2107192A1 (ko)
DE (1) DE69307240T2 (ko)
ES (1) ES2096828T3 (ko)
MX (1) MX9305979A (ko)
PL (1) PL300521A1 (ko)
RO (1) RO112273B1 (ko)
SI (1) SI9300505A (ko)
TW (1) TW328950B (ko)
ZA (1) ZA937192B (ko)

Families Citing this family (143)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9119955D0 (en) * 1991-09-18 1991-10-30 Imperial College Treatment of aqueous supplies containing organic material
ES2151958T3 (es) * 1994-04-14 2001-01-16 Du Pont Composiciones de catalizador de niquel y fosfito bidentado para hidrocianacion de monoolefinas.
US5756855A (en) * 1994-08-19 1998-05-26 Union Carbide Chemicals & Plastics Technology Corporation Stabilization of phosphite ligands in hydroformylation process
US5648553A (en) * 1994-12-09 1997-07-15 Mitsubishi Chemical Corporation Method for producing aldehydes
US5672766A (en) * 1994-12-12 1997-09-30 Mitsubishi Chemical Corporation Method for producing aldehydes
US5821378A (en) * 1995-01-27 1998-10-13 E. I. Du Pont De Nemours And Company Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles
IN187044B (ko) * 1995-01-27 2002-01-05 Du Pont
US5648554A (en) * 1995-04-12 1997-07-15 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)
JPH0977713A (ja) * 1995-09-19 1997-03-25 Mitsubishi Chem Corp アルデヒド類の製造方法
US5786517A (en) * 1995-12-06 1998-07-28 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5731472A (en) * 1995-12-06 1998-03-24 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5886235A (en) * 1995-12-06 1999-03-23 Union Carbide Chemicals & Plastics Technology Corporation. Metal-ligand complex catalyzed processes
US5763671A (en) * 1995-12-06 1998-06-09 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation processes
US5767321A (en) * 1995-12-06 1998-06-16 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5741942A (en) * 1996-11-26 1998-04-21 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
EA001218B1 (ru) * 1995-12-06 2000-12-25 Юнион Карбайд Кемикалз Энд Пластикс Текнолоджи Корпорейшн Способ отделения кислотных соединений фосфора в присутствии металл-органофосфитного комплексного катализатора
US5789625A (en) * 1995-12-06 1998-08-04 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
EP0839787A1 (en) † 1996-11-04 1998-05-06 Dsm N.V. Process for the preparation of an aldehyde
US6153795A (en) * 1996-08-09 2000-11-28 Aag Industries, Inc. Ethyleneimine-containing resins, manufacture, and use for chemical separations
US6090950A (en) * 1996-08-23 2000-07-18 Zeeland Chemicals, Inc. Chiral hydride complexes
US6274773B1 (en) 1996-11-04 2001-08-14 Dsm Process for the continuous preparation of alkyl 5-formylvalerate compounds using homogeneous rhodium hydroformylation catalysts
EP0839794A1 (en) * 1996-11-04 1998-05-06 Dsm N.V. Process for the continuous preparation of an alkyl 5-formylvalerate compound
US5917095A (en) * 1996-11-26 1999-06-29 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
ZA9610314B (en) * 1996-11-26 1998-09-07 Union Carbide Chem Plastic Metal-ligand complex catalyzed processes
US5874640A (en) * 1996-11-26 1999-02-23 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US6127582A (en) * 1997-08-27 2000-10-03 Shell Oil Company Hydroformylation process
EP0903333B1 (en) * 1997-09-18 2001-11-07 Shell Internationale Researchmaatschappij B.V. Hydroformylation process
JP3812095B2 (ja) 1997-10-28 2006-08-23 三菱化学株式会社 アルデヒド類の製造方法及びこれに用いるビスホスファイト
US6156936A (en) * 1998-03-16 2000-12-05 Shell Oil Company Hydroformylation of olefin feeds containing dienes
EP0943597B1 (en) * 1998-03-16 2003-06-04 Shell Internationale Researchmaatschappij B.V. Hydroformylation of olefin feeds containing dienes
US6229052B1 (en) * 1998-05-29 2001-05-08 E. I. Du Pont De Nemours And Company Hydroformylation of olefins using supported bis(phosphorus) ligands
US6090987A (en) * 1998-07-06 2000-07-18 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
KR100434589B1 (ko) * 1998-11-25 2004-09-08 현대석유화학 주식회사 하이드로포르밀레이션반응용촉매의배위자,이를포함하는촉매및이를이용한혼합올레핀의하이드로포르밀레이션방법
DE19940249A1 (de) * 1999-08-25 2001-03-01 Celanese Chem Europe Gmbh Verfahren zur Herstellung von Aldehyden
US6610891B1 (en) 1999-12-03 2003-08-26 Mitsubishi Chemical Corporation Method of producing aldehydes
EP1249444A1 (en) * 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process for forming an aldehyde
EP1249438A1 (en) * 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process for producing an aldehyde
EP1249441A1 (en) 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process
US6693219B2 (en) 2001-06-02 2004-02-17 Eastman Chemical Company Epoxide stabilization of fluorophosphite-metal catalyst system in a hydroformylation process
US6831035B2 (en) 2002-01-22 2004-12-14 Eastman Kodak Company Stabilization of fluorophosphite-containing catalysts
DE10220801A1 (de) * 2002-05-10 2003-11-20 Oxeno Olefinchemie Gmbh Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste
US6664427B1 (en) * 2002-08-29 2003-12-16 E. I. Du Pont De Nemours And Company Process for preparing aldehyde compounds
WO2004020380A1 (de) * 2002-08-31 2004-03-11 Oxeno Olefinchemie Gmbh Verfahren zur hydroformylierung von olefinisch ungesättigten verbindungen, insbesondere olefinen in gegenwart cyclischer kohlensäureester
MXPA05007334A (es) * 2003-01-16 2005-09-30 Teijin Fibers Ltd Hilos de filamentos combinados de poliester de contraccion diferente.
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
GB0322246D0 (en) * 2003-09-23 2003-10-22 Exxonmobil Chem Patents Inc Improvement in or relating to isobutylene
GB0322247D0 (en) 2003-09-23 2003-10-22 Exxonmobil Chem Patents Inc Improvement in or relating to an isobutylene containing stream
CN1309728C (zh) * 2004-07-30 2007-04-11 中国科学院上海有机化学研究所 一类手性有机－无机高分子组装体催化剂、合成方法及用途
EP1776328B1 (en) 2004-08-02 2018-04-18 Dow Technology Investments LLC Stabilization of a hydroformylation process
JP2006306815A (ja) * 2005-04-28 2006-11-09 Mitsubishi Chemicals Corp アルデヒドの製造方法
BRPI0808297B1 (pt) * 2007-03-20 2017-02-07 Dow Technology Investments Llc processo de hidroformilação
US7674937B2 (en) * 2008-05-28 2010-03-09 Eastman Chemical Company Hydroformylation catalysts
WO2010021863A1 (en) * 2008-08-19 2010-02-25 Dow Technology Investments Llc Hydroformylation process using a symmetric bisphosphite ligand for improved control over product isomers
EP2349560A4 (en) 2008-11-14 2013-10-09 Univ Kansas POLYMER-CARRED EXTRACT METAL CATALYST COMPLEXES AND METHOD FOR THEIR USE
MY158433A (en) 2009-03-31 2016-10-14 Dow Technology Investments Llc Hydroformylation process with a doubly open-ended bisphosphite ligand
WO2011046781A1 (en) 2009-10-16 2011-04-21 Dow Technology Investments Llc Gas phase hydroformylation process
EP2581362B1 (en) 2009-12-22 2018-01-31 Dow Technology Investments LLC Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process
RU2546110C2 (ru) 2009-12-22 2015-04-10 Дау Текнолоджи Инвестментс Ллс Регулирование соотношения альдегид нормального строения: альдегид изо-строения в процессе гидроформилирования со смешанным лигандом регулированием парциального давления синтез-газа
US8598390B2 (en) 2009-12-22 2013-12-03 Dow Technology Investments Llc Controlling the normal:ISO aldehyde ratio in a mixed ligand hydroformylation process
JP5652052B2 (ja) * 2010-08-24 2015-01-14 三菱化学株式会社 アルデヒドの製造方法
JP2014502254A (ja) 2010-10-05 2014-01-30 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 ヒドロホルミル化の方法
MX346922B (es) 2010-11-12 2017-04-05 Dow Technology Investments Llc Moderación de suciedad en procesos de hidroformilación mediante adición de agua.
KR20130135286A (ko) 2010-12-23 2013-12-10 바스프 에스이 열가소성 엘라스토머 조성물 및 그의 제조 방법
US8513468B2 (en) 2010-12-30 2013-08-20 Eastman Chemical Company Process for removing degradation acids from hydroformylation reactions
SA112330271B1 (ar) * 2011-04-18 2015-02-09 داو تكنولوجى انفستمنتس ال ال سى تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء
CN102826974B (zh) * 2011-06-17 2015-11-25 中国石油化工股份有限公司 一种丙烯氢甲酰化反应制备丁醛的方法
WO2013066712A1 (en) 2011-10-31 2013-05-10 Dow Technology Investments Llc Preventing solvent of crystallization in production of polyphosphite ligands
RU2606629C2 (ru) 2011-12-20 2017-01-10 Дау Текнолоджи Инвестментс Ллс Усовершенствованный способ гидроформилирования
RU2660899C2 (ru) 2011-12-30 2018-07-11 Басф Се Кристаллический сольват и несольватированные формы 6,6'-[[3,3',5,5'-тетракис(1,1-диметилэтил)-[1,1'-бифенил]-2,2'-диил]бис(окси)]бис-дибензо[d,f][1,3,2]-диоксафосфепина
MX363617B (es) 2011-12-30 2019-03-28 Basf Se Metodo para la purificacion de compuestos de difosfitos organicos.
PL2822921T3 (pl) 2012-03-07 2018-11-30 Basf Se SPOSÓB INTEGRACJI CIEPŁA PRZY UWODORNIANIU I DESTYLACJI C<sub>3</sub>-C<sub>20</sub>- ALDEHYDÓW
US8889917B2 (en) 2012-04-12 2014-11-18 Basf Se Method of supplementing the catalyst in continuous hydroformylation
PL2836474T3 (pl) 2012-04-12 2018-06-29 Basf Se Sposób uzupełniania katalizatora podczas ciągłego hydroformylowania
WO2013183796A1 (en) 2012-06-04 2013-12-12 Lg Chem, Ltd. Hydroformylation method having improved catalyst stability in reaction
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
CN104602815B (zh) 2012-08-29 2017-03-01 陶氏技术投资有限责任公司 催化剂制备方法
WO2014051975A1 (en) 2012-09-25 2014-04-03 Dow Technology Investments Llc Process for stabilizing a phosphite ligand against degradation
EP2802550B1 (de) 2012-10-12 2016-01-13 Evonik Degussa GmbH Langzeitstabiles verfahren zur herstellung von c5-aldehyden
DE102013219510A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Gemisch von Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung
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
CN104513143A (zh) 2013-09-26 2015-04-15 陶氏技术投资有限责任公司 加氢甲酰化方法
KR102291247B1 (ko) 2013-10-28 2021-08-20 롬 앤드 하아스 컴패니 메타크롤레인을 분리하는 방법
TWI654177B (zh) 2013-10-31 2019-03-21 德商巴斯夫歐洲公司 製備羧酸酯的方法及其作爲塑化劑的用途
CA2932240A1 (en) 2013-12-06 2015-06-11 Basf Se Softener composition which contains tetrahydrofuran derivatives and 1,2-cyclohexane dicarboxylic acid esters
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
CN106103399B (zh) 2013-12-19 2019-07-09 陶氏技术投资有限责任公司 氢甲酰化方法
CN105899585A (zh) 2014-01-09 2016-08-24 巴斯夫欧洲公司 包含呋喃衍生物和1,2-环己烷二甲酸酯的增塑剂组合物
PL3126319T3 (pl) 2014-03-31 2020-01-31 Dow Technology Investments Llc Proces hydroformylowania
TWI678359B (zh) 2014-04-22 2019-12-01 德商巴斯夫歐洲公司 製備羧酸酯的方法及其作爲塑化劑的用途
DE102015207291A1 (de) 2014-04-24 2016-03-10 Basf Se Weichmacher-Zusammensetzung, die Furanderivate und 1,2-Cyclohexandicarbonsäureester enthält
JP6694396B2 (ja) 2014-05-14 2020-05-13 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 安定化された有機リン化合物
TW201605945A (zh) 2014-07-08 2016-02-16 巴斯夫歐洲公司 包含二羧酸的酯及１，２－環己烷二羧酸的酯之模製化合物
TW201609628A (zh) 2014-07-08 2016-03-16 巴斯夫歐洲公司 包含脂族二羧酸二酯及對苯二甲酸二烷基酯之塑化劑組成物
TWI706979B (zh) 2014-08-19 2020-10-11 德商巴斯夫歐洲公司 包含聚合二羧酸酯的塑化劑組成物
TWI686444B (zh) 2014-09-04 2020-03-01 德商巴斯夫歐洲公司 包含聚合二羧酸酯的塑化劑組成物
TW201619120A (zh) 2014-10-09 2016-06-01 巴斯夫歐洲公司 包含飽和二羧酸之環烷基酯及對苯二甲酯之塑化劑組成物
TW201619119A (zh) 2014-10-09 2016-06-01 巴斯夫歐洲公司 包含飽和二羧酸之環烷基酯及１，２－環己烷二羧酸酯的塑化劑組成物
US9914792B2 (en) 2014-11-10 2018-03-13 Basf Se Ethylene-propylheptyl(meth-)acrylate copolymers
RU2706647C2 (ru) 2015-01-30 2019-11-19 Басф Се Пластифицирующая композиция, содержащая полимерные сложные эфиры дикарбоновых кислот и диалкиловые сложные эфиры терефталевой кислоты
CA2999998A1 (en) 2015-09-30 2017-04-06 Basf Se Plasticizer composition containing polymeric dicarboxylic acid esters and 1,2-cyclohexane dicarboxylic acid esters
RU2727926C9 (ru) 2015-09-30 2021-05-21 Басф Се Пластифицирующая композиция, содержащая полимерные сложные эфиры дикарбоновых кислот и сложные диэфиры дикарбоновых кислот
PL3356456T3 (pl) 2015-09-30 2019-11-29 Basf Se Kompozycja plastyfikatora zawierająca polimerowe estry kwasu dikarboksylowego i estry dialkilowe kwasu tereftalowego
RU2719438C2 (ru) 2015-11-10 2020-04-17 Дау Текнолоджи Инвестментс Ллк Способ получения альдегидов
CN105498855A (zh) * 2015-12-08 2016-04-20 中国海洋石油总公司 提高醚后c4羰基合成反应铑-双膦催化剂稳定性的方法
WO2017125458A1 (de) 2016-01-20 2017-07-27 Basf Se Weichmacher-zusammensetzung, die aliphatische dicarbonsäureester und diester, die unter 1,2-cyclohexandicarbonsäureestern und terephthalsäureestern ausgewählt sind, enthält
RU2751511C9 (ru) 2016-02-11 2021-08-18 Дау Текнолоджи Инвестментс Ллк Способы превращения олефинов в спирты, простые эфиры или их комбинации
CN107141204B (zh) 2016-03-01 2022-03-15 陶氏技术投资有限责任公司 氢甲酰化工艺
RU2724349C2 (ru) 2016-03-18 2020-06-23 Дау Текнолоджи Инвестментс Ллк Способ гидроформилирования
PL3433309T3 (pl) 2016-03-23 2020-11-16 Basf Se Kompozycja polimerowa, zawierająca diester cykloalkilowo-alkilowy kwasu dikarboksylowego jako plastyfikator
WO2018024597A1 (de) 2016-08-01 2018-02-08 Basf Se Weichmacher-zusammensetzung
WO2018024591A1 (de) 2016-08-01 2018-02-08 Basf Se Weichmacher-zusammensetzung
RU2019105682A (ru) 2016-08-01 2020-09-01 Басф Се Композиция пластификатора
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
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
EP3700882B1 (en) 2017-10-25 2022-10-26 Dow Technology Investments LLC Process to reduce heavies formation in a solution comprising aldehyde compounds formed during a hydroformylation process
CN111278560B (zh) 2017-11-13 2023-07-21 陶氏技术投资有限责任公司 从氢甲酰化方法回收铑的方法
TWI793216B (zh) * 2017-12-07 2023-02-21 美商陶氏科技投資公司 氫甲醯化方法
WO2019185409A1 (de) 2018-03-29 2019-10-03 Basf Se Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung
KR20210013702A (ko) 2018-05-30 2021-02-05 다우 테크놀로지 인베스트먼츠 엘엘씨. 하이드로포밀화 공정에서 촉매의 탈활성화를 느리게 하고/하거나 테트라포스핀 리간드 사용을 느리게 하는 방법
WO2019231613A1 (en) 2018-05-30 2019-12-05 Dow Technology Investments Llc Catalyst composition comprising the combination of a monophopsphine, a tetraphosphine ligand and a hydroformylation process using it
CA3100779A1 (en) 2018-05-30 2019-12-05 Dow Technology Investments Llc Methods of controlling hydroformylation processes
KR20210098486A (ko) 2018-11-29 2021-08-10 다우 테크놀로지 인베스트먼츠 엘엘씨. 히드로포르밀화 공정
SG11202109997PA (en) * 2019-03-29 2021-10-28 Kowa Co Novel azaindole derivative
EP3747860B1 (de) 2019-06-04 2023-07-26 Basf Se Neue weichmacher auf cyclohexanon-basis
US20220143590A1 (en) 2019-06-27 2022-05-12 Dow Technology Investments Llc Process to prepare solution from hydroformylation process for precious metal recovery
SE1930237A1 (en) * 2019-07-05 2020-11-17 Perstorp Ab A use of epoxide in order to reduce the formation of heavy ends in a hydroformylation process
TW202126385A (zh) 2019-11-05 2021-07-16 美商陶氏科技投資有限公司 自氫甲醯化製程回收銠之方法
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
JP2023553108A (ja) 2020-12-14 2023-12-20 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における触媒金属の責務を改善するためのプロセス
BR112023017950A2 (pt) 2021-03-31 2023-10-10 Dow Technology Investments Llc Processo de hidroformilação contínuo
CN113402367A (zh) * 2021-06-16 2021-09-17 上海华谊（集团）公司 连续氢甲酰化反应中调节正异比的方法
CN114027296A (zh) * 2021-11-10 2022-02-11 山东农业大学 用于防治松材线虫及其媒介昆虫的纳米农药制剂
KR20240108441A (ko) 2021-11-11 2024-07-09 다우 테크놀로지 인베스트먼츠 엘엘씨. 히드로포르밀화 공정으로부터의 로듐의 회수 공정
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
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
WO2024129290A1 (en) 2022-12-13 2024-06-20 Dow Technology Investments Llc Process to minimize polyphosphine usage by making use of degradation products
WO2024133358A1 (de) 2022-12-21 2024-06-27 Basf Se Weichmacher-verbindung
WO2024133359A1 (de) 2022-12-21 2024-06-27 Basf Se Weichmacher
WO2024153687A1 (de) 2023-01-19 2024-07-25 Basf Se Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH348284A (de) * 1956-11-30 1960-08-15 Geigy Ag J R Verfahren zur Stabilisierung von Estern von Säuren des drei- oder fünfwertigen Phosphors oder von solche Ester enthaltenden Gemischen
US3533298A (en) * 1968-08-28 1970-10-13 Gerber Scientific Instr Co Lead screw and nut mechanism
US4224255A (en) * 1978-06-15 1980-09-23 General Electric Company Process for the production of aldehydes and alcohols from olefinically unsaturated compounds by hydroformylation with suppression of olefin hydrogenation
ZA827645B (en) * 1981-11-12 1983-08-31 Union Carbide Corp Catalyst stabilizer
EP0090283B1 (de) * 1982-03-27 1985-12-04 BASF Aktiengesellschaft Verfahren zur Herstellung von Olefinen aus Methanol/Dimethylether
DE3234701A1 (de) * 1982-09-18 1984-04-05 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur herstellung von aldehyden
GB8334359D0 (en) * 1983-12-23 1984-02-01 Davy Mckee Ltd Process
DE3413427A1 (de) * 1984-04-10 1985-10-17 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur herstellung von aldehyden
US4650894A (en) * 1984-07-05 1987-03-17 Argus Chemical Corporation Tris-organophosphite compositions having improved hydrolytic stability
US4578523A (en) * 1985-05-29 1986-03-25 Ruhrchemie Aktiengesellschaft Process for the preparation of aldehydes
US4668651A (en) * 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
BR8806809A (pt) * 1987-12-24 1989-08-29 Union Carbide Corp Processo de hidrocarbonilacao para a producao de um aldeido ou uma mistura de uma cetona e um aldeido;catalisador intermediario;processo para a producao de catalisador de complexo de rodio;e processo de hidroacilacao
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
US5095061A (en) * 1990-07-13 1992-03-10 The Dow Chemical Company Process to reduce propenyl polyethers in hydroxyfunctional polyethers
TW213465B (ko) * 1991-06-11 1993-09-21 Mitsubishi Chemicals Co Ltd

Also Published As

Publication number Publication date
SI9300505A (en) 1994-06-30
EP0590613A3 (ko) 1994-04-27
US5288918A (en) 1994-02-22
DE69307240D1 (de) 1997-02-20
EP0590613A2 (en) 1994-04-06
CN1092401A (zh) 1994-09-21
ES2096828T3 (es) 1997-03-16
EP0590613B1 (en) 1997-01-08
JPH06199728A (ja) 1994-07-19
TW328950B (en) 1998-04-01
RO112273B1 (ro) 1997-07-30
BR9303934A (pt) 1994-07-26
CA2107192A1 (en) 1994-03-30
KR100198688B1 (ko) 1999-06-15
JP2942693B2 (ja) 1999-08-30
ZA937192B (en) 1994-04-21
CN1056364C (zh) 2000-09-13
MX9305979A (es) 1995-01-31
PL300521A1 (en) 1994-04-05
DE69307240T2 (de) 1997-05-07
AU4864393A (en) 1994-04-14

Similar Documents

Publication Publication Date Title
KR940006983A (ko) 하이드로포밀화 방법
KR940007047A (ko) 포스파이트 리간드를 안정화하는 방법
US4774361A (en) Transition metal complex catalyzed reactions
KR930001327B1 (ko) 비스-포스파이트 화합물
US4769498A (en) Transition metal complex catalyzed processes
US5929289A (en) Stabilization of phosphite ligands in hydroformylation process
US5202297A (en) Rhodium hydroformylation catalysts containing bisphosphite ligands
KR930000454A (ko) 히드로포르밀화법 및 여기에 사용되는 비스포스파이트 화합물
KR970700156A (ko) 5-포르밀발레르 산 및 5-포르밀발러레이트 에스테르의 제조 방법(process for the preparation of 5-formylvaleric acid and 5-formylvalerate ester)
KR940005526A (ko) 1,6- 헥산디알을 제조하기 위한 하이드로포밀화 방법
KR900014032A (ko) 카르보닐화 촉매 시스템 및 신규 포스핀과 그의 제조방법
KR900003183A (ko) 이온성 포스파이트 및 균질 전이금속 촉매화 공정에서 이의 용도
KR850700240A (ko) 전이금속 착화합물 촉매화 반응
SE8704533D0 (sv) Hydroformylation using low volatile phosphine ligands
MY117848A (en) Process to prepare a terminal aldehyde
FR2392948A1 (fr) Procede de production d&#39;acides et d&#39;esters carboxyliques
KR830002795A (ko) 액상 조성물중 트리오르가노 포스핀의 제거방법
WO1996016923A1 (en) Process for the preparation of an aldehyde
KR890009836A (ko) 시클로프로판 유도체
KR860700247A (ko) 로듐착화합물 촉매를 사용하여 알코올로부터 카복실산을 제조하는 방법
KR880011070A (ko) 카복실산의 제조방법
KR930006068A (ko) 노볼락 수지 및 이의 제조방법
KR930001342B1 (ko) 카보닐화 방법
KR860700248A (ko) 로듐 착화합물 촉매를 사용하여 유기포르 메이트 에스테르로부터 카복실산을 제조하는 방법
JP3291421B2 (ja) ヒドロホルミル化方法におけるホスフィットリガンドの安定化

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20130201

Year of fee payment: 15

EXPY Expiration of term