GB1448090A - Catalytic hydroformylation process employing rhodium coordination complexes - Google Patents

Catalytic hydroformylation process employing rhodium coordination complexes

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Publication number
GB1448090A
GB1448090A GB5507873A GB5507873A GB1448090A GB 1448090 A GB1448090 A GB 1448090A GB 5507873 A GB5507873 A GB 5507873A GB 5507873 A GB5507873 A GB 5507873A GB 1448090 A GB1448090 A GB 1448090A
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United Kingdom
Prior art keywords
specified
rhodium
compound
cod
ligand
Prior art date
Legal status (The legal status 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 status listed.)
Expired
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GB5507873A
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Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Publication of GB1448090A publication Critical patent/GB1448090A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • 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
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
    • 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
    • B01J31/20—Carbonyls
    • 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
    • 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
    • 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
    • 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
    • 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
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

1448090 Oxo synthesis; rhodium-containing organic complexes MONSANTO CO 28 Nov 1973 [29 Nov 1972] 55078/73 Headings C2C C2B C2J and C2P An aldehyde is obtained by hydroformylation of a C 2 to C 30 olefinically unsaturated compound by contacting the unsturated compound, CO and H 2 at 60‹ to 180‹ C. in the presence of a catalyst of a rhodium complex of the formula [Rh(CO) x L y ]+Anwherein is a number from 1 to 5, y is a number from 1 to 4 such that x+y=5, L is a tertiary organophosphorus, tertiary organo-arsenic, -antimony, or -nitrogen compound having from 3 to 90 carbon atoms, or a binary organosulphur compound having 2 to 60 carbon atoms, and Anis a non-co-ordinating anionic moiety, e.g. BPh 4 - (where Ph is phenyl), BF 4 -, ClO 4 -, PF 6 -, NO 3 - or SiF 6 -. Specified ligands L are P(C 6 H 5 ) 3 , P(C 6 H 5 O) 3 , As(C 6 H 5 ) 3 , Sb(C 6 H 5 ) 3 , N(C 6 H 5 ) 3 and S(C 2 H 5 ) 2 and specified complexes are An excess of the ligand L may be used as liquid reaction medium and this ligand may be the same as or different from that present in the complex. Various other liquids may also be used as reaction medium, and several such liquids are specified. The catalyst may be used in the liquid phase or dispersed on a porous solid support such as silica, carbon or alumina. Several olefinic compounds suitable for use as feedstock are specified and examples are given for the hydroformylation of 1-hexene, 1-octene, isomerized octene, isomerized dodecene, 1-dodecene, styrene, α-methylstyrene, ethyl vinyl ether, ethylene, propylene, vinyl acetate, isomerized pentenes, ethyl acrylate, iso-butylene and 1,5-hexadiene. The cationic rhodium complexes of the given formula are prepared by adding to a methanol solution of the ligand L, under a nitrogen atmosphere, an appropriate rhodium precursor such as [Rh(COD)Cl] 2 where COD is 1,5-cyclooctadiene, stirring the mixture and after 30 minutes adding a salt of the anion An-, e.g. NaBPh 4 or NaBF 4 , sitrring the suspension for 30 minutes and then recovering the precipitated product which is then washed with ether, dried, and then treated, e.g. in acetone solution, with carbon monoxide. An example is given for the production of Rh(COD)(Ph 3 P) 2 BPH 4 as intermediate and its conversion to by treatment with CO in acetone solution.
GB5507873A 1972-11-29 1973-11-28 Catalytic hydroformylation process employing rhodium coordination complexes Expired GB1448090A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31062172A 1972-11-29 1972-11-29

Publications (1)

Publication Number Publication Date
GB1448090A true GB1448090A (en) 1976-09-02

Family

ID=23203366

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5507873A Expired GB1448090A (en) 1972-11-29 1973-11-28 Catalytic hydroformylation process employing rhodium coordination complexes

Country Status (9)

Country Link
JP (1) JPS4982614A (en)
AT (1) AT333716B (en)
BE (1) BE807908A (en)
CA (1) CA1022934A (en)
DE (1) DE2359377A1 (en)
FR (1) FR2207896B1 (en)
GB (1) GB1448090A (en)
IT (1) IT1002034B (en)
NL (1) NL7316127A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018161A1 (en) * 1979-04-11 1980-10-29 DAVY McKEE (LONDON) LIMITED Aldehyde-ethers and process for their production
US4260828A (en) * 1980-04-16 1981-04-07 Union Carbide Corporation Hydroformylation process
US4496769A (en) * 1982-06-11 1985-01-29 Davy Mckee (London) Limited Process for the preparation of aldehydes by hydroformylation of olefins
US4496768A (en) * 1982-06-11 1985-01-29 Davy Mckee Limited Process for the production of aldehydes by hydroformylation of alpha-olefins
GB2183643A (en) * 1985-11-29 1987-06-10 Nat Distillers Chem Corp Olefin hydroformylation
GB2274457A (en) * 1993-01-25 1994-07-27 Shell Int Research Hydroformylation of unsaturated carbonyl compounds

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55151521A (en) * 1979-05-15 1980-11-26 Toyo Soda Mfg Co Ltd Preparation of alcohol
CA1327365C (en) * 1988-06-29 1994-03-01 Stephen R. Stobart Process for catalytic hydroformylation
CN111318307A (en) * 2018-12-17 2020-06-23 中国石油化工股份有限公司 Catalyst composition, application thereof and method for hydroformylation of vinyl acetate

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018161A1 (en) * 1979-04-11 1980-10-29 DAVY McKEE (LONDON) LIMITED Aldehyde-ethers and process for their production
US4260828A (en) * 1980-04-16 1981-04-07 Union Carbide Corporation Hydroformylation process
US4496769A (en) * 1982-06-11 1985-01-29 Davy Mckee (London) Limited Process for the preparation of aldehydes by hydroformylation of olefins
US4496768A (en) * 1982-06-11 1985-01-29 Davy Mckee Limited Process for the production of aldehydes by hydroformylation of alpha-olefins
GB2183643A (en) * 1985-11-29 1987-06-10 Nat Distillers Chem Corp Olefin hydroformylation
GB2183643B (en) * 1985-11-29 1990-06-13 Nat Distillers Chem Corp Olefin hydroformylation
GB2274457A (en) * 1993-01-25 1994-07-27 Shell Int Research Hydroformylation of unsaturated carbonyl compounds

Also Published As

Publication number Publication date
BE807908A (en) 1974-05-28
FR2207896B1 (en) 1977-03-04
FR2207896A1 (en) 1974-06-21
IT1002034B (en) 1976-05-20
CA1022934A (en) 1977-12-20
AT333716B (en) 1976-12-10
NL7316127A (en) 1974-05-31
DE2359377A1 (en) 1974-06-06
JPS4982614A (en) 1974-08-08
ATA999273A (en) 1976-04-15

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