GB1138601A - Improvements in catalytic reactions - Google Patents

Improvements in catalytic reactions

Info

Publication number
GB1138601A
GB1138601A GB50983/64A GB5098364A GB1138601A GB 1138601 A GB1138601 A GB 1138601A GB 50983/64 A GB50983/64 A GB 50983/64A GB 5098364 A GB5098364 A GB 5098364A GB 1138601 A GB1138601 A GB 1138601A
Authority
GB
United Kingdom
Prior art keywords
hydroformylation
halogen
rhcl
rhodium
pseudo
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
Application number
GB50983/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB50983/64A priority Critical patent/GB1138601A/en
Priority to DE19651793616 priority patent/DE1793616C3/en
Priority to DE19651518236 priority patent/DE1518236A1/en
Priority to FR42369A priority patent/FR1459643A/en
Priority to US514132A priority patent/US3501531A/en
Publication of GB1138601A publication Critical patent/GB1138601A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium compounds
    • C07F15/008—Rhodium compounds without a metal-carbon linkage
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
    • C07C5/25—Migration of carbon-to-carbon double bonds
    • C07C5/2506—Catalytic processes
    • C07C5/2562—Catalytic processes with hydrides or organic compounds
    • C07C5/2593—Catalytic processes with hydrides or organic compounds containing phosphines, arsines, stibines or bismuthines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

1,138,601. Catalytic hydrogenation, hydroformylation and carbonylation processes and complexes containing phosphorus, arsenic or antimony. G. WILKINSON. 13 Dec., 1965 [15 Dec., 1964 (2); 16 Feb., 1965; 5 Oct., 1965], Nos. 50983/64, 50984/64, 6676/65 and 42138/65. Headings C2C and C2J. [Also in Divisions C1 and C5] Alcohols, aldehydes, carboxylic acids and halogenated hydrocarbons are produced in a hydrogenation, hydroformylation or carbonylation process, an unsaturated organic compound is reacted with hydrogen and/or carbon monoxide in the presence of a liquid medium which contains dissolved therein as catalyst a halogen or pseudo-halogen-containing complex which has been formed from a halide or pseudo halide of a platinum group metal and at least one ligand which is either: (a) an organic isocyanide; or (b) an organic compound having in its molecule an atom of an element of Group V B or VI B of the Periodic Table, said atom possessing a lone pair of electrons, including phosphorus tri-isocyanate and phosphorus tri-isothiocyanate; or (c) (when the complex is formed from a rhodium or iridium halide and the said process is one of hydroformylation) a stannous or germanium-II halide. In the hydrogenation process the unsaturated organic compound may contain an olefinic, acetylenic or carbonyl bond and in the hydroformylation or carbonylation process the unsaturated organic compound is an ethylenically- or acetylenically-unsaturated hydrocarbon or substituted hydrocarbon. The process may be carried out between 50‹ and 150‹ C. and at a pressure of 5 to 100 atmospheres and the liquid medium may comprise a solvent or co-solvent for the catalytic complex (e.g. lower alkanols, ethers or aliphatic or aromatic hydrocarbons) or it may be constituted by the unsaturated organic reactant or, as the reaction proceeds, the resulting product. The aldehydes obtained by the above hydroformylation reaction may be hydrogenated to the corresponding primary alcohols using the same or different complex catalyst or the said alcohol may be obtained directly from an olefinic or acetylenic hydrocarbon in a single step involving both hydroformylation and hydrogenation. Preferred ligands of type (b) include tertiary amines, phosphines, arsines and stibines; organic nitriles, sulphoxides, phosphine oxides, dialkyl sulphides and mercaptans. The complex catalyst may be represented by the formula LnM<SP>V</SP>Xy, where each L represents a ligand as defined above, M is the platinum group metal, X represents a halogen atom or a pseudo-halogen group (i.e. CN-, CNO- or CNS-) and V is the valency of the metal, and may be neutral or a positively charged ion and may have a tetragonal, octahedral or S-co-ordinate quasi octahedral structure. Specified catalysts are (Ph 3 P) 3 RhCl 3 , (Ph 3 As) 3 RhCl 3 , (Ph 3 As) 2 PtCl 2 , [(Ph 2 EtP) 6 Ru 2 Cl 3 ]Cl, (Ph 3 P) 3 RhCl, Ru(Ph 3 P) 2 Cl 3 MeOH, [Ru 2 (PhEt 2 P) 6 Cl 3 ]Cl, Ru(Ph 3 P) 3 Cl 3 , Ru(Ph 3 P) 4 Cl 2 , Ru(Ph 2 PCH 2 CH 2 PPh 2 ) 2 Cl 2 , Ru(Ph 3 As) 2 Cl 3 MeOH and (SnCl 2 ) 2 RhCl 2 Rh(SnCl 2 ) 2 wherein Ph represents phenyl, Et represents ethyl and Me represents methyl some of which are new compounds. The invention also comprises as new compounds the rhodium-I compounds of the formula (R 3 Z)Rh<SP>I</SP>X where R 3 Z represents a tertiary phosphine, arsine or stibine and X represents a halogen atom or a pseudo-halogen group. These compounds may be obtained by refluxing an excess of a tertiary phosphine, arsine or stibine with a rhodium trihalide in a solvent, e.g. alcohol, or by using tertiary phosphines, arsines or stibines to displace other ligands from rhodium-I complexes.
GB50983/64A 1964-12-15 1964-12-15 Improvements in catalytic reactions Expired GB1138601A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB50983/64A GB1138601A (en) 1964-12-15 1964-12-15 Improvements in catalytic reactions
DE19651793616 DE1793616C3 (en) 1964-12-15 1965-12-14 Rhodium complexes
DE19651518236 DE1518236A1 (en) 1964-12-15 1965-12-14 Catalytic process
FR42369A FR1459643A (en) 1964-12-15 1965-12-15 Process of hydrogenation, hydroformylation and carbonylation using halogenated complexes
US514132A US3501531A (en) 1964-12-15 1965-12-15 Hydroformylation process

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB50983/64A GB1138601A (en) 1964-12-15 1964-12-15 Improvements in catalytic reactions
GB667665 1965-02-16
GB4213865 1965-10-05

Publications (1)

Publication Number Publication Date
GB1138601A true GB1138601A (en) 1969-01-01

Family

ID=27254877

Family Applications (1)

Application Number Title Priority Date Filing Date
GB50983/64A Expired GB1138601A (en) 1964-12-15 1964-12-15 Improvements in catalytic reactions

Country Status (1)

Country Link
GB (1) GB1138601A (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2047748A1 (en) * 1969-10-01 1971-04-08 Johnson, Matthey & Co Ltd Lon don Catalytic process and catalyst produced by means of the same
DE2062703A1 (en) * 1969-12-22 1971-07-01 Union Carbide Corp , New York, N Y (V St A) Hydroformylation process
DE1793069A1 (en) * 1967-08-03 1972-02-03 Union Carbide Corp Process for the manufacture of products containing oxygen
US3883580A (en) * 1972-02-09 1975-05-13 Monsanto Co Asymmetric reduction of ketones to form optically active alcohols
US3937742A (en) * 1970-03-06 1976-02-10 Atlantic Richfield Company Hydroformylation process using catalyst comprising platinum group metal on support having separate alumina phase
US3968147A (en) * 1972-02-09 1976-07-06 Monsanto Company Asymmetric reduction of ketones to form optically active alcohols
US3981925A (en) * 1972-05-08 1976-09-21 Texaco Inc. Selective hydroformylation process using homogeneous catalysts
US3996293A (en) * 1972-05-08 1976-12-07 Texaco Inc. Selective hydroformylation process
FR2376105A1 (en) * 1976-12-30 1978-07-28 Gen Electric PROCESS FOR MANUFACTURING BUTANEDIOLS AND SUBSTITUTE BUTANEDIOLS
US4469895A (en) * 1982-10-21 1984-09-04 Texaco Inc. Process for preparing alcohols from olefins and synthesis gas
US4562284A (en) * 1983-03-02 1985-12-31 Shell Oil Company Process for the preparation of carboxylic acids
GB2183643A (en) * 1985-11-29 1987-06-10 Nat Distillers Chem Corp Olefin hydroformylation
US4973719A (en) * 1988-10-28 1990-11-27 Ranbaxy Laboratories Limited Process for the production of alpha-6-deoxytetracyclines
US4978771A (en) * 1985-11-19 1990-12-18 Bayer Aktiengesellschaft Process for the selective hydrogenation of unsatuated compounds
US4987242A (en) * 1988-10-28 1991-01-22 Jagmohan Khanna Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines
US4997959A (en) * 1989-04-03 1991-03-05 Ranbaxy Laboratories Limited Process for the production of alpha-6-deoxytetracyclines
USRE34548E (en) * 1985-11-19 1994-02-15 Bayer Aktiengesellschaft Process for the selective hydrogenation of unsaturated compounds

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1793069A1 (en) * 1967-08-03 1972-02-03 Union Carbide Corp Process for the manufacture of products containing oxygen
DE2047748A1 (en) * 1969-10-01 1971-04-08 Johnson, Matthey & Co Ltd Lon don Catalytic process and catalyst produced by means of the same
DE2062703A1 (en) * 1969-12-22 1971-07-01 Union Carbide Corp , New York, N Y (V St A) Hydroformylation process
US3937742A (en) * 1970-03-06 1976-02-10 Atlantic Richfield Company Hydroformylation process using catalyst comprising platinum group metal on support having separate alumina phase
US3883580A (en) * 1972-02-09 1975-05-13 Monsanto Co Asymmetric reduction of ketones to form optically active alcohols
US3968147A (en) * 1972-02-09 1976-07-06 Monsanto Company Asymmetric reduction of ketones to form optically active alcohols
US3981925A (en) * 1972-05-08 1976-09-21 Texaco Inc. Selective hydroformylation process using homogeneous catalysts
US3996293A (en) * 1972-05-08 1976-12-07 Texaco Inc. Selective hydroformylation process
FR2376105A1 (en) * 1976-12-30 1978-07-28 Gen Electric PROCESS FOR MANUFACTURING BUTANEDIOLS AND SUBSTITUTE BUTANEDIOLS
US4469895A (en) * 1982-10-21 1984-09-04 Texaco Inc. Process for preparing alcohols from olefins and synthesis gas
US4562284A (en) * 1983-03-02 1985-12-31 Shell Oil Company Process for the preparation of carboxylic acids
US4978771A (en) * 1985-11-19 1990-12-18 Bayer Aktiengesellschaft Process for the selective hydrogenation of unsatuated compounds
USRE34548E (en) * 1985-11-19 1994-02-15 Bayer Aktiengesellschaft Process for the selective hydrogenation of unsaturated compounds
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
US4973719A (en) * 1988-10-28 1990-11-27 Ranbaxy Laboratories Limited Process for the production of alpha-6-deoxytetracyclines
US4987242A (en) * 1988-10-28 1991-01-22 Jagmohan Khanna Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines
US4997959A (en) * 1989-04-03 1991-03-05 Ranbaxy Laboratories Limited Process for the production of alpha-6-deoxytetracyclines

Similar Documents

Publication Publication Date Title
GB1138601A (en) Improvements in catalytic reactions
US3725305A (en) Catalyst compositions formed by transition metal cations and methods of making and using such catalysts
US3933919A (en) Hydroformylation of mono-α-olefins and mono-α-acetylenes
Evans et al. Hydroformylation of alkenes by use of rhodium complex catalysts
US4179403A (en) Resin-ligand-metal complex compositions
US3168553A (en) Reactions of olefins with carbon monoxide
EP0971940B1 (en) Diphosphines
US4306085A (en) Hydroformylation process using resin-ligand-metal catalyst
Edwards et al. Synthesis and Reactivity of the Unusual Five-Coordinate Hydrido− Hydroxo Complex OsH (OH)(CO)(PiPr3) 2
GB1466803A (en) Optically active bissphosphines and metal complex catalysts containing them
US4284835A (en) Hydrogenation process
US3857900A (en) Hydrogenation of aldehydes using triarylphosphine rhodium halogenoid catalysts
Milstein Mild, low-pressure carbonylation of (. pi.-allyl) palladium complexes
KR100251076B1 (en) Process of preparation of alcohol through hydrofication of carbonylic compounds
Fogg et al. A comparison of catalytic activity for imine hydrogenation using Ru ditertiary phosphine complexes, including chiral systems
US4317936A (en) Hydroformylation process using resin-ligand-metal catalyst
Rowsell et al. Bridging methylene to bridging acyl conversion in heterobinuclear Rh/Ru complexes: Models for adjacent-metal involvement in bimetallic catalysts
US3939219A (en) Hyrogenation of unsaturated compounds
Sommovigo et al. Mild reduction of α, β-unsaturated ketones and aldehydes with an oxygen-activated palladium catalyst
US5103065A (en) Transition metal complexes as catalysts for hydrogenation hydroformylation and cyclotrimerization
Phillips et al. A new class of rhodium (I) κ1-P and κ2-P, N complexes with rigid PTN (R) ligands (PTN= 7-phospha-3-methyl-1, 3, 5-triazabicyclo [3.3. 1] nonane)
Markó Hydroformylation of Olefins with Carbonyl Derivates of the Nobles Metals as Catalysts
DE60010304T2 (en) METHOD FOR CARBONYLATING AN ACETYLENICALLY UNSATURATED COMPOUND
Lindsay et al. Hydrogenation of alkenes by diruthenium (II) tetraacetate
Trzeciak et al. Homogeneous rhodium complex-catalyzed hydroformylation and related reactions of functionally substituted olefins