WO2003053571A3 - Catalyst comprising a complex of a metal of the viii. sub-group based on a ligand with an unbridged heterophosphacyclohexane structural element - Google Patents

Catalyst comprising a complex of a metal of the viii. sub-group based on a ligand with an unbridged heterophosphacyclohexane structural element Download PDF

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Publication number
WO2003053571A3
WO2003053571A3 PCT/EP2002/014690 EP0214690W WO03053571A3 WO 2003053571 A3 WO2003053571 A3 WO 2003053571A3 EP 0214690 W EP0214690 W EP 0214690W WO 03053571 A3 WO03053571 A3 WO 03053571A3
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WO
WIPO (PCT)
Prior art keywords
ligand
catalyst
complex
heterophosphacyclohexane
unbridged
Prior art date
Application number
PCT/EP2002/014690
Other languages
German (de)
French (fr)
Other versions
WO2003053571A2 (en
Inventor
Thomas Mackewitz
Rocco Paciello
Original Assignee
Basf Ag
Thomas Mackewitz
Rocco Paciello
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 Basf Ag, Thomas Mackewitz, Rocco Paciello filed Critical Basf Ag
Priority to EP02796715A priority Critical patent/EP1458479A2/en
Publication of WO2003053571A2 publication Critical patent/WO2003053571A2/en
Publication of WO2003053571A3 publication Critical patent/WO2003053571A3/en

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    • 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
    • C07F9/6596—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having atoms other than oxygen, sulfur, selenium, tellurium, nitrogen or phosphorus as ring hetero atoms
    • 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
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2438—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member and further hetero atoms as ring members, excluding the positions adjacent to P
    • 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
    • B01J31/2466—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 comprising aliphatic or saturated rings
    • 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
    • B01J31/2471—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 with more than one complexing phosphine-P 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
    • 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
    • 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
    • C07F9/547—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
    • C07F9/657163—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 the ring phosphorus atom being bound to at least one carbon atom
    • 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
    • C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/6584—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero 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
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • 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
    • 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
    • B01J2531/824—Palladium
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (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)
  • Catalysts (AREA)

Abstract

The invention relates to a catalyst, comprising at least one complex of a platinate metal of the VIII. sub-group with at least one ligand with at least one unbridged heterophosphacyclohexane structural element, whereby the ligand is selected from heterophosphacyclohexanes of general formula (I), where A1, A2, A3 independently = O, S, SO2, NRa, SiRbRc or CRdRe with the proviso that at least one of the groups A1, A2, or A3 is not CRdRe, with the further proviso that at least one of the groups R2 to R5 is not hydrogen, a method for hydroformylation in the presence of such a catalyst and the use thereof, amongst other things for hydroformylation. The invention further relates to a method for hydrocyanation in the presence of a catalyst comprising a complex of such a ligand with nickel.
PCT/EP2002/014690 2001-12-21 2002-12-20 Catalyst comprising a complex of a metal of the viii. sub-group based on a ligand with an unbridged heterophosphacyclohexane structural element WO2003053571A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP02796715A EP1458479A2 (en) 2001-12-21 2002-12-20 Catalyst comprising a complex of a metal of the viii. sub-group based on a heterophosphacyclohexane ligand

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10163400.5 2001-12-21
DE2001163400 DE10163400A1 (en) 2001-12-21 2001-12-21 Catalyst comprising a complex of a metal of subgroup VIII based on a heterophosphacyclohexane ligand

Publications (2)

Publication Number Publication Date
WO2003053571A2 WO2003053571A2 (en) 2003-07-03
WO2003053571A3 true WO2003053571A3 (en) 2003-11-27

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PCT/EP2002/014690 WO2003053571A2 (en) 2001-12-21 2002-12-20 Catalyst comprising a complex of a metal of the viii. sub-group based on a ligand with an unbridged heterophosphacyclohexane structural element

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EP (1) EP1458479A2 (en)
DE (1) DE10163400A1 (en)
WO (1) WO2003053571A2 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3424897A4 (en) 2016-03-01 2019-10-09 Kuraray Co., Ltd. Method of producing dialdehyde compound

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1198815A (en) * 1966-08-23 1970-07-15 Gulf Research Development Co Catalytic Hydroformylation of Olefins
GB1263623A (en) * 1968-05-15 1972-02-16 Basf Ag Production of aldehydes and alcohols by the oxo method
GB1273042A (en) * 1968-09-18 1972-05-03 Basf Ag Oxo synthesis of aldehydes and/or alcohols
GB1398717A (en) * 1971-09-03 1975-06-25 Ici Ltd Tertiary phospines and their use as catalysts components in the production of aldehydes and alcohols
EP1120162A2 (en) * 2000-01-24 2001-08-01 Degussa AG Use of catalysts with a higher molecular weight in an asymmetrical continous hydration reaction, ligands and catalysts
DE10023468A1 (en) * 2000-05-12 2001-11-15 Basf Ag Novel ligand-metal complex, useful for hydroformylation of ethylenically unsaturated compounds, comprises ruthenium, rhodium, palladium and platinum and a monophosphine, monophosphinite or monophosphinamidite ligand

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1198815A (en) * 1966-08-23 1970-07-15 Gulf Research Development Co Catalytic Hydroformylation of Olefins
GB1263623A (en) * 1968-05-15 1972-02-16 Basf Ag Production of aldehydes and alcohols by the oxo method
GB1273042A (en) * 1968-09-18 1972-05-03 Basf Ag Oxo synthesis of aldehydes and/or alcohols
GB1398717A (en) * 1971-09-03 1975-06-25 Ici Ltd Tertiary phospines and their use as catalysts components in the production of aldehydes and alcohols
EP1120162A2 (en) * 2000-01-24 2001-08-01 Degussa AG Use of catalysts with a higher molecular weight in an asymmetrical continous hydration reaction, ligands and catalysts
DE10023468A1 (en) * 2000-05-12 2001-11-15 Basf Ag Novel ligand-metal complex, useful for hydroformylation of ethylenically unsaturated compounds, comprises ruthenium, rhodium, palladium and platinum and a monophosphine, monophosphinite or monophosphinamidite ligand

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KHADIULLIN, R. SH. ET AL: "FTIR - spectroscopy study of the three-dimensional structure of 1,3,5-diazaphosphorinane complexes with transitional metals", XP002252179, retrieved from STN Database accession no. 119:17175 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KHAIRULLINA, R. Z. ET AL: "Hydrogenation of heptyne-1 in the presence of palladium(II) complexes with cyclic aminomethylphosphines", XP002252178, retrieved from STN Database accession no. 122:164027 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MEYER, H. ET AL: "Intramolecular mobility of.eta.3-allylpalladium chloride complexes of different phosphines studied by two dimensional NMR spectroscopy", XP002243142, retrieved from STN Database accession no. 101:230734 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; YANILKIN, V. V. ET AL: "Kinetics of electrochemical reduction of 2-carbomethoxy-2-methyl-1,1- dichlorocyclopropane by double mediator systems containing anthracene and complexes of PtII, PdII, or NiII with cyclic (aminomethyl)phosphines", XP002252177, retrieved from STN Database accession no. 123:227475 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ZSCHUNKE, A. ET AL: "Intramolecular mobility of phosphine-3.eta.-allylpalladium chloride complexes", XP002243141, retrieved from STN Database accession no. 98:179588 *
IZVESTIYA AKADEMII NAUK, SERIYA KHIMICHESKAYA (1994), (3), 414-16 *
JOURNAL OF MOLECULAR STRUCTURE (1993), 293, 85-8 *
JOURNAL OF ORGANOMETALLIC CHEMISTRY (1984), 269(2), 209-16 *
NEFTEKHIMIYA (1994), 34(4), 332-5 *
OSTERMEIER, MARKUS ET AL: "Mono- and bidentate phosphinanes-new chiral ligands and their application in catalytic asymmetric hydrogenations", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION (2002), 41(4), 612-614, XP002252176 *
VEEN VAN DER L A ET AL: "NEW PHOSPHACYCLIC DIPHOSPHINES FOR RHODIUM-CATALYZED HYDROFORMAYLATION", ORGANOMETALLICS, WASHINGTON, DC, US, vol. 18, no. 23, 8 November 1999 (1999-11-08), pages 4765 - 4777, XP000964505, ISSN: 0276-7333 *
ZEITSCHRIFT FUER ANORGANISCHE UND ALLGEMEINE CHEMIE (1982), 494, 189-95 *

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Publication number Publication date
EP1458479A2 (en) 2004-09-22
WO2003053571A2 (en) 2003-07-03
DE10163400A1 (en) 2003-07-03

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