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WO2002064250A3 - Procede de carbonylation de composes a insaturation ethylenique, composition de diphosphine bidentate utilisee dans ce procede et procedes de preparation de cette composition de diphosphine bidentate - Google Patents

Procede de carbonylation de composes a insaturation ethylenique, composition de diphosphine bidentate utilisee dans ce procede et procedes de preparation de cette composition de diphosphine bidentate Download PDF

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Publication number
WO2002064250A3
WO2002064250A3 PCT/EP2002/001036 EP0201036W WO02064250A3 WO 2002064250 A3 WO2002064250 A3 WO 2002064250A3 EP 0201036 W EP0201036 W EP 0201036W WO 02064250 A3 WO02064250 A3 WO 02064250A3
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WO
WIPO (PCT)
Prior art keywords
bidentate diphosphine
diphosphine composition
bidentate
composition
carbonylation
Prior art date
Application number
PCT/EP2002/001036
Other languages
English (en)
Other versions
WO2002064250A2 (fr
Inventor
Peter Arnoldy
Cornelius Mark Bolinger
Eit Drent
Michael Rolf Eberhard
Hero Jan Heeres
Der Linden Adrianus Johann Van
Wilhelmus Petrus Mul
Paul Gerard Pringle
Jacoba Catherina Lu Suykerbuyk
Kwoliang David Tau
Original Assignee
Shell Int Research
Peter Arnoldy
Cornelius Mark Bolinger
Eit Drent
Michael Rolf Eberhard
Hero Jan Heeres
Der Linden Adrianus Johann Van
Wilhelmus Petrus Mul
Paul Gerard Pringle
Jacoba Catherina Lu Suykerbuyk
Kwoliang David Tau
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 Shell Int Research, Peter Arnoldy, Cornelius Mark Bolinger, Eit Drent, Michael Rolf Eberhard, Hero Jan Heeres, Der Linden Adrianus Johann Van, Wilhelmus Petrus Mul, Paul Gerard Pringle, Jacoba Catherina Lu Suykerbuyk, Kwoliang David Tau filed Critical Shell Int Research
Priority to EP02724159A priority Critical patent/EP1358009A2/fr
Priority to JP2002564038A priority patent/JP2004527484A/ja
Priority to AU2002254887A priority patent/AU2002254887A1/en
Priority to CA002436215A priority patent/CA2436215A1/fr
Publication of WO2002064250A2 publication Critical patent/WO2002064250A2/fr
Publication of WO2002064250A3 publication Critical patent/WO2002064250A3/fr

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    • 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
    • B01J31/2461—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 ring members in the condensed ring system or in a further ring
    • B01J31/248—Bridged ring systems, e.g. 9-phosphabicyclononane
    • 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
    • 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
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/505—Preparation; Separation; Purification; Stabilisation
    • C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
    • C07F9/5072—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure P-H
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/505—Preparation; Separation; Purification; Stabilisation
    • C07F9/5095—Separation; Purification; Stabilisation
    • 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
    • C07F9/6568—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 atoms as the only ring hetero atoms
    • C07F9/65683—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 atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • 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
    • 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
    • B01J2531/828—Platinum

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé de carbonylation de composés à insaturation éthylénique, éventuellement substitués, consistant à mettre en réaction du monoxyde de carbone et un coréactant en présence d'un système catalyseur. Le système catalyseur comprend (a) une source de cations métalliques du groupe du Pt, (b) une composition de diphosphine bidentate. Plus de 60 % en poids du diphosphine bidentate présent dans la composition de diphosphine bidentate est représenté par la formule générale (II) X1-R-X2 dans laquelle X1 et X2 représentent, de manière indépendante, un groupe phosphabicycloalkyle symétrique, éventuellement substitué, constitué d'au moins 5 atomes cycliques, et R représente un groupe de pontage organique divalent, reliant les deux atomes de phosphore. L'invention concerne aussi une composition de diphosphine bidentate dans laquelle plus de 60 % en poids de diphosphine bidentate est représenté par la formule générale (II) ) X1-R-X2 dans laquelle X1 et X2 représentent, de manière indépendante, un groupe phosphabicycloalkyle symétrique, éventuellement substitué, constitué d'au moins 5 atomes cycliques, et R représente un groupe de pontage organique divalent, reliant les deux atomes de phosphore, sous réserve que le diphosphine bidentate ne soit pas du 1,3-PP'bis(9-phosphabicyclo[3.3.1]nonyl)propane. Elle concerne enfin des procédés de préparation d'un telle composition de diphosphine bidentate.
PCT/EP2002/001036 2001-01-31 2002-01-31 Procede de carbonylation de composes a insaturation ethylenique, composition de diphosphine bidentate utilisee dans ce procede et procedes de preparation de cette composition de diphosphine bidentate WO2002064250A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP02724159A EP1358009A2 (fr) 2001-01-31 2002-01-31 Procede de carbonylation de composes a insaturation ethylenique, composition de diphosphine bidentate utilisee dans ce procede et procedes de preparation de cette composition de diphosphine bidentate
JP2002564038A JP2004527484A (ja) 2001-01-31 2002-01-31 エチレン性不飽和化合物のカルボニル化方法、その方法において使用される二座ジホスフィン組成物、およびその二座ジホスフィン組成物の調製方法
AU2002254887A AU2002254887A1 (en) 2001-01-31 2002-01-31 Process for the carbonylation of ethylenically unsaturated compounds, bidentate diphosphine composition used in this process and processes for preparation of this bidentate diphosphine composition
CA002436215A CA2436215A1 (fr) 2001-01-31 2002-01-31 Procede de carbonylation de composes a insaturation ethylenique, composition de diphosphine bidentate utilisee dans ce procede et procedes de preparation de cette composition de diphosphine bidentate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01300866.9 2001-01-31
EP01300866 2001-01-31

Publications (2)

Publication Number Publication Date
WO2002064250A2 WO2002064250A2 (fr) 2002-08-22
WO2002064250A3 true WO2002064250A3 (fr) 2003-01-30

Family

ID=8181678

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/001036 WO2002064250A2 (fr) 2001-01-31 2002-01-31 Procede de carbonylation de composes a insaturation ethylenique, composition de diphosphine bidentate utilisee dans ce procede et procedes de preparation de cette composition de diphosphine bidentate

Country Status (7)

Country Link
EP (1) EP1358009A2 (fr)
JP (1) JP2004527484A (fr)
CN (1) CN1535180A (fr)
AU (1) AU2002254887A1 (fr)
CA (1) CA2436215A1 (fr)
WO (1) WO2002064250A2 (fr)
ZA (1) ZA200305228B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7098369B2 (en) 2002-09-26 2006-08-29 Shell Oil Company Process for the production of primary alcohols
EP1542798B1 (fr) * 2002-09-26 2007-11-14 Shell Internationale Researchmaatschappij B.V. Procede d'hydroformylation d'un compose ethyleniquement insature en utilisant un compose diphosphine bidentate avec un groupe-pont comprenant des atomes de carbone sp2 hybridises lies a les atomes de phosphore
CN108456228B (zh) * 2017-02-22 2020-11-13 李达刚 一种小空障有机膦配体及其制备方法与在乙烯制1-辛烯及1-己烯中的应用

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527818A (en) * 1965-11-26 1970-09-08 Shell Oil Co Oxo alcohols using catalysts comprising ditertiary phosphines
US3647915A (en) * 1969-11-04 1972-03-07 Shell Oil Co Ethylene oligomerization
GB2074166A (en) * 1980-04-16 1981-10-28 Union Carbide Corp Process for removing triorganophosphine from an organic liquid
EP0495547A2 (fr) * 1991-01-15 1992-07-22 Shell Internationale Researchmaatschappij B.V. Carbonylation d'oléfines
EP0529698A2 (fr) * 1991-08-30 1993-03-03 Shell Internationale Researchmaatschappij B.V. Procédé pour la préparation d'alcools
US5304686A (en) * 1993-07-13 1994-04-19 Shell Oil Company Process for making 3-hydroxypropanal and 1,3-propanediol
CA2086285A1 (fr) * 1992-12-24 1994-06-25 Colleen Elizabeth Micklethwaite Methode de preparation de derives de disubstitution vicinale de composes bis(diorganophosphino)
WO1995005354A1 (fr) * 1993-08-19 1995-02-23 Shell Internationale Research Maatschappij B.V. Procede d'hydroformylation
WO1997003943A1 (fr) * 1995-07-17 1997-02-06 Shell Internationale Research Maatschappij B.V. Procede de carbonylation continue d'olefines
GB2306344A (en) * 1995-10-25 1997-05-07 Shell Int Research Catalysed hydroformylation
WO1998034941A1 (fr) * 1997-02-10 1998-08-13 Albemarle Corporation Procede de purification des trihydrocarbylphosphines utilisant du methanol
EP0864576A1 (fr) * 1997-03-10 1998-09-16 F. Hoffmann-La Roche Ag Nouveaux dérivés amidophosphine-phosphinites
US5811590A (en) * 1995-10-25 1998-09-22 Shell Oil Company Hydroformylation process
EP0872482A2 (fr) * 1997-04-15 1998-10-21 Union Carbide Chemicals & Plastics Technology Corporation Procédé de la fabrication d'epsilon-caprolactone et/ou leur hydrates et/ou leur esters
US6037500A (en) * 1996-06-14 2000-03-14 The Penn State Research Foundation Asymmetric synthesis catalyzed by transition metal complexes with cyclic chiral phosphine ligands
US6080898A (en) * 1997-07-23 2000-06-27 Shell Oil Company Hydrogenolysis of glycerol
WO2000052017A1 (fr) * 1999-03-03 2000-09-08 Cytec Technology Corp. Preparation de 9-hydrocarbyle-9-phosphabicyclononanes
WO2001087899A1 (fr) * 2000-05-17 2001-11-22 Shell Internationale Research Maatschappij B.V. Ligand bidentate utile dans le systeme catalytique

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527818A (en) * 1965-11-26 1970-09-08 Shell Oil Co Oxo alcohols using catalysts comprising ditertiary phosphines
US3647915A (en) * 1969-11-04 1972-03-07 Shell Oil Co Ethylene oligomerization
GB2074166A (en) * 1980-04-16 1981-10-28 Union Carbide Corp Process for removing triorganophosphine from an organic liquid
EP0495547A2 (fr) * 1991-01-15 1992-07-22 Shell Internationale Researchmaatschappij B.V. Carbonylation d'oléfines
EP0529698A2 (fr) * 1991-08-30 1993-03-03 Shell Internationale Researchmaatschappij B.V. Procédé pour la préparation d'alcools
CA2086285A1 (fr) * 1992-12-24 1994-06-25 Colleen Elizabeth Micklethwaite Methode de preparation de derives de disubstitution vicinale de composes bis(diorganophosphino)
US5304686A (en) * 1993-07-13 1994-04-19 Shell Oil Company Process for making 3-hydroxypropanal and 1,3-propanediol
WO1995005354A1 (fr) * 1993-08-19 1995-02-23 Shell Internationale Research Maatschappij B.V. Procede d'hydroformylation
WO1997003943A1 (fr) * 1995-07-17 1997-02-06 Shell Internationale Research Maatschappij B.V. Procede de carbonylation continue d'olefines
GB2306344A (en) * 1995-10-25 1997-05-07 Shell Int Research Catalysed hydroformylation
US5811590A (en) * 1995-10-25 1998-09-22 Shell Oil Company Hydroformylation process
US6037500A (en) * 1996-06-14 2000-03-14 The Penn State Research Foundation Asymmetric synthesis catalyzed by transition metal complexes with cyclic chiral phosphine ligands
WO1998034941A1 (fr) * 1997-02-10 1998-08-13 Albemarle Corporation Procede de purification des trihydrocarbylphosphines utilisant du methanol
EP0864576A1 (fr) * 1997-03-10 1998-09-16 F. Hoffmann-La Roche Ag Nouveaux dérivés amidophosphine-phosphinites
EP0872482A2 (fr) * 1997-04-15 1998-10-21 Union Carbide Chemicals & Plastics Technology Corporation Procédé de la fabrication d'epsilon-caprolactone et/ou leur hydrates et/ou leur esters
US6080898A (en) * 1997-07-23 2000-06-27 Shell Oil Company Hydrogenolysis of glycerol
WO2000052017A1 (fr) * 1999-03-03 2000-09-08 Cytec Technology Corp. Preparation de 9-hydrocarbyle-9-phosphabicyclononanes
WO2001087899A1 (fr) * 2000-05-17 2001-11-22 Shell Internationale Research Maatschappij B.V. Ligand bidentate utile dans le systeme catalytique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DOWNING J H ET AL: "A simple procedure for the separation of the catalytically important phosphabicyclononane isomers", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 16, 21 August 1997 (1997-08-21), pages 1527 - 1528, XP002137315, ISSN: 1359-7345 *

Also Published As

Publication number Publication date
CN1535180A (zh) 2004-10-06
AU2002254887A1 (en) 2002-08-28
JP2004527484A (ja) 2004-09-09
ZA200305228B (en) 2004-05-13
WO2002064250A2 (fr) 2002-08-22
EP1358009A2 (fr) 2003-11-05
CA2436215A1 (fr) 2002-08-22

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