TWI253448B - Hydroformylation process and process for the preparation of a supported rhodium bisphosphite hydroformylation catalyst - Google Patents

Hydroformylation process and process for the preparation of a supported rhodium bisphosphite hydroformylation catalyst Download PDF

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Publication number
TWI253448B
TWI253448B TW088108921A TW88108921A TWI253448B TW I253448 B TWI253448 B TW I253448B TW 088108921 A TW088108921 A TW 088108921A TW 88108921 A TW88108921 A TW 88108921A TW I253448 B TWI253448 B TW I253448B
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Taiwan
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group
supported
ligand
aryloxy
cns
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TW088108921A
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English (en)
Chinese (zh)
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Emilio E Bunel
Patrick Michael Burke
Joe Douglas Druliner
Leo Ernest Manzer
Kenneth Gene Moloy
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Invista Tech Sarl
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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)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (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)
TW088108921A 1998-05-29 1999-08-27 Hydroformylation process and process for the preparation of a supported rhodium bisphosphite hydroformylation catalyst TWI253448B (en)

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US8715198P 1998-05-29 1998-05-29

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TW088108921A TWI253448B (en) 1998-05-29 1999-08-27 Hydroformylation process and process for the preparation of a supported rhodium bisphosphite hydroformylation catalyst

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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)

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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
WO2002040573A1 (fr) * 2000-11-17 2002-05-23 Mitsubishi Rayon Co., Ltd. Binaphtyles optiquement actifs a support solide et procede de preparation de derives d'aminonitrile asymetriques a l'aide de ceux-ci
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
CN1289539C (zh) * 2001-11-26 2006-12-13 因维斯塔技术有限公司 载体上的双(磷)配体及其在催化中的应用
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
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
EP2004622B1 (en) * 2006-04-10 2011-12-14 Merck Patent GmbH Chiral binaphthyl sulfates for use as liquid crystal materials
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
CA2743720C (en) * 2008-11-14 2019-03-12 University Of Kansas Polymer-supported transition metal catalyst complexes and methods of use
FR2941455B1 (fr) 2009-01-29 2011-02-11 Rhodia Operations Procede de fabrication de composes comprenant des fonctions nitriles
EP2488539B2 (en) 2009-10-16 2023-12-20 Dow Technology Investments LLC Gas phase hydroformylation process
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
CN108473628B (zh) * 2015-12-25 2020-12-22 东洋合成工业株式会社 化合物和有机材料的制造方法
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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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
EP1082285B1 (en) 2004-07-21
DE69918828D1 (de) 2004-08-26
CA2330153A1 (en) 1999-12-09
EP1082285A1 (en) 2001-03-14
KR100580420B1 (ko) 2006-05-16
ATE271532T1 (de) 2004-08-15
JP2002516891A (ja) 2002-06-11
JP4309057B2 (ja) 2009-08-05
US6229052B1 (en) 2001-05-08
ES2224669T3 (es) 2005-03-01
BR9911205A (pt) 2001-10-09
DE69918828T2 (de) 2005-08-04
US20020052531A1 (en) 2002-05-02
US6369257B1 (en) 2002-04-09
KR20010043883A (ko) 2001-05-25
WO1999062855A1 (en) 1999-12-09
MY121451A (en) 2006-01-28
ID26775A (id) 2001-02-08

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