DE69918828T2 - Hydroformylierung von olefinen unter verwendung von bis(phosphor) trägerliganden - Google Patents

Hydroformylierung von olefinen unter verwendung von bis(phosphor) trägerliganden Download PDF

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Publication number
DE69918828T2
DE69918828T2 DE69918828T DE69918828T DE69918828T2 DE 69918828 T2 DE69918828 T2 DE 69918828T2 DE 69918828 T DE69918828 T DE 69918828T DE 69918828 T DE69918828 T DE 69918828T DE 69918828 T2 DE69918828 T2 DE 69918828T2
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supported
mmol
rhodium
aryl
alkyl
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German (de)
English (en)
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DE69918828D1 (de
Inventor
E. Emilio BUNEL
Michael Patrick BURKE
Douglas Joe DRULINER
Ernest Leo MANZER
Gene Kenneth MOLOY
Manxue Wang
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Invista Technologies SARL USA
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Invista Technologies SARL USA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • 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
    • B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
    • B01J31/1658—Polymer immobilised coordination complexes, e.g. organometallic complexes immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
    • 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
    • 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
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • 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
    • B01J31/24—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
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (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)
DE69918828T 1998-05-29 1999-05-26 Hydroformylierung von olefinen unter verwendung von bis(phosphor) trägerliganden Expired - Lifetime DE69918828T2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US8715198P 1998-05-29 1998-05-29
US87151P 1998-05-29
PCT/US1999/011557 WO1999062855A1 (en) 1998-05-29 1999-05-26 Hydroformylation of olefins using supported bis(phosphorus) ligands

Publications (2)

Publication Number Publication Date
DE69918828D1 DE69918828D1 (de) 2004-08-26
DE69918828T2 true DE69918828T2 (de) 2005-08-04

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DE69918828T Expired - Lifetime DE69918828T2 (de) 1998-05-29 1999-05-26 Hydroformylierung von olefinen unter verwendung von bis(phosphor) trägerliganden

Country Status (13)

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US (2) US6229052B1 (enExample)
EP (1) EP1082285B1 (enExample)
JP (1) JP4309057B2 (enExample)
KR (1) KR100580420B1 (enExample)
AT (1) ATE271532T1 (enExample)
BR (1) BR9911205A (enExample)
CA (1) CA2330153A1 (enExample)
DE (1) DE69918828T2 (enExample)
ES (1) ES2224669T3 (enExample)
ID (1) ID26775A (enExample)
MY (1) MY121451A (enExample)
TW (1) TWI253448B (enExample)
WO (1) WO1999062855A1 (enExample)

Families Citing this family (28)

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US6420611B1 (en) * 1999-09-20 2002-07-16 E. I. Du Pont De Nemours And Company Composition comprising polymeric phosphite
JP2001139691A (ja) * 1999-11-16 2001-05-22 Mitsubishi Chemicals Corp ３価リン含有重合体触媒によるアルデヒド類の製造方法および新規なホスファイト含有重合体
DE10002976A1 (de) * 2000-01-24 2001-07-26 Degussa Molekulargewichtsvergrößerte Liganden für asymmetrische homogen lösliche Hydrierkatalysatoren, Verfahren zu deren Herstellung und Verwendung
JP4091837B2 (ja) * 2000-11-17 2008-05-28 三菱レイヨン株式会社 固相担持光学活性ビナフチルおよび固相担持光学活性ビナフチルを用いた不斉アミノニトリル誘導体の製造法
JP4796235B2 (ja) * 2001-03-27 2011-10-19 上野製薬株式会社 ビナフトール誘導体金属塩およびその製法
US20030100803A1 (en) 2001-11-26 2003-05-29 Lu Helen S.M. 3-Alkylated-5,5',6,6',7,7,'8,8'-octahydro-2,2'-binaphthols and 3,3'-dialkylated-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthols and processes for making them
US20030135014A1 (en) * 2001-11-26 2003-07-17 Radu Nora S. Polymeric, phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions
US6660876B2 (en) 2001-11-26 2003-12-09 E. I. Du Pont De Nemours And Company Phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions
US6984604B2 (en) 2001-11-26 2006-01-10 Invista North America S.A.R.L. Supported bis(phosphorus) ligands and their use in the catalysis
US6664427B1 (en) * 2002-08-29 2003-12-16 E. I. Du Pont De Nemours And Company Process for preparing aldehyde compounds
JP4328080B2 (ja) * 2002-10-30 2009-09-09 三菱化学株式会社 固体担持有機リン化合物、遷移金属錯体、及び触媒反応方法
DE10349343A1 (de) * 2003-10-23 2005-06-02 Basf Ag Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden
DE102004033575B3 (de) 2004-07-09 2006-04-13 Schunk Ultraschalltechnik Gmbh Anordnung zum Verschweißen von Werkstücken
US20060258875A1 (en) * 2005-05-10 2006-11-16 Clementine Reyes Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts
US8097229B2 (en) * 2006-01-17 2012-01-17 Headwaters Technology Innovation, Llc Methods for manufacturing functionalized inorganic oxides and polymers incorporating same
KR101442270B1 (ko) * 2006-04-10 2014-09-22 메르크 파텐트 게엠베하 액정 물질로서 사용하기 위한 키랄 바이나프틸 설페이트
JP4020155B2 (ja) * 2006-07-31 2007-12-12 三菱化学株式会社 有機二リン基架橋型重合体
FR2926816B1 (fr) 2008-01-25 2010-05-14 Rhodia Operations Procede de fabrication de composes comprenant des fonctions nitriles
FR2932477B1 (fr) 2008-06-17 2013-01-18 Rhodia Operations Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
FR2937321B1 (fr) 2008-10-21 2010-10-22 Rhodia Operations Procede de fabrication de composes comprenant des fonctions nitriles
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
FR2941455B1 (fr) 2009-01-29 2011-02-11 Rhodia Operations Procede de fabrication de composes comprenant des fonctions nitriles
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
JP5932556B2 (ja) * 2012-08-07 2016-06-08 富士フイルム株式会社 液晶組成物、高分子、フィルムおよびコレステリック液晶
JP6109604B2 (ja) * 2013-03-05 2017-04-05 嶋田　豊司 オクタヒドロビナフチル誘導体
US9611203B2 (en) 2013-12-11 2017-04-04 Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences Method for olefin hydroformylation reaction using solid heterogeneous catalyst
JP6867303B2 (ja) 2015-12-25 2021-04-28 東洋合成工業株式会社 化合物及び有機材料の製造方法
CN109942750B (zh) * 2019-01-14 2021-06-25 青岛科技大学 含有双齿亚磷酰胺配体的多孔有机聚合物及其制备方法和应用

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TW343195B (en) 1996-03-15 1998-10-21 Dsm Nv Process to prepare a terminal aldehyde
EP0839787A1 (en) * 1996-11-04 1998-05-06 Dsm N.V. Process for the preparation of an aldehyde
US5710344A (en) 1996-11-08 1998-01-20 E. I. Du Pont De Nemours And Company Process to prepare a linear aldehyde
JP3892931B2 (ja) 1997-03-11 2007-03-14 高砂香料工業株式会社 ２個のビニル基を有する光学活性ホスフィン誘導体、それをモノマーとするポリマー、及びそれらの遷移金属錯体
JP3892932B2 (ja) 1997-03-11 2007-03-14 高砂香料工業株式会社 ビニル基を有する光学活性ホスフィン誘導体、それをモノマーとするポリマー、及びそれらの遷移金属錯体
US6121184A (en) 1997-07-29 2000-09-19 E. I. Du Pont De Nemours And Company Supported bis(phosphorus) ligands

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Publication number Publication date
EP1082285A1 (en) 2001-03-14
EP1082285B1 (en) 2004-07-21
WO1999062855A1 (en) 1999-12-09
KR100580420B1 (ko) 2006-05-16
MY121451A (en) 2006-01-28
ID26775A (id) 2001-02-08
JP2002516891A (ja) 2002-06-11
DE69918828D1 (de) 2004-08-26
US20020052531A1 (en) 2002-05-02
US6369257B1 (en) 2002-04-09
US6229052B1 (en) 2001-05-08
KR20010043883A (ko) 2001-05-25
BR9911205A (pt) 2001-10-09
CA2330153A1 (en) 1999-12-09
ES2224669T3 (es) 2005-03-01
ATE271532T1 (de) 2004-08-15
TWI253448B (en) 2006-04-21
JP4309057B2 (ja) 2009-08-05

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