GB1121643A - Hydrogenation process - Google Patents

Hydrogenation process

Info

Publication number
GB1121643A
GB1121643A GB5275/66A GB527566A GB1121643A GB 1121643 A GB1121643 A GB 1121643A GB 5275/66 A GB5275/66 A GB 5275/66A GB 527566 A GB527566 A GB 527566A GB 1121643 A GB1121643 A GB 1121643A
Authority
GB
United Kingdom
Prior art keywords
yr1r11r111
hydrogenated
group
compounds containing
rhodium
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
GB5275/66A
Inventor
Robert Stevenson Coffey
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB5275/66A priority Critical patent/GB1121643A/en
Priority to DE19671618529 priority patent/DE1618529A1/en
Publication of GB1121643A publication Critical patent/GB1121643A/en
Expired legal-status Critical Current

Links

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
    • B01J31/24—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
    • B01J31/16—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
    • B01J31/1895—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 arsenic or antimony
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or 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
    • C07C5/02—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
    • 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
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Organic compounds containing one or more olefinic or acetylenic bonds are hydrogenated by contact with molecular hydrogen in a liquid phase comprising a solution of a rhodium complex comprising (a) rhodium, (b) an anionic element or group, and (c) a compound of formula YR1R11R111, where Y is arsenic, antimon or phosphorus and the R's are the same or different hydrocarbon or substituted hydrocarbon groups or heterocyclic groups, the molar ratio of (a) : (b) : (c) being in the range 1:1:1 to 1:1:4. The rhodium complex may be of the type [RhX(YR1R11R111)2]n or RhH2X(YR1R11R111)3, or may be formed in situ from (RhXZ2)n and YR1R11R111, where X in each case is the anionic element or group, and Z is a mono- or di-olefin. X may be cyanide, cyanate, carboxylate, SnCl3- or halogen, preferably chlorine. An inert solvent may be present. Compounds containing acetylenic bonds may be partially or completely hydrogenated as desired by controlling the hydrogen uptake. Compounds which may be hydrogenated include butadiene, octene-1, octene-2, diisobutene, cyclohexene, vinyl cyclohexene, styrene and phenyl acetylene (giving styrene or ethyl benzene as desired).ALSO:Organic compounds containing one or more olefinic or acetylenic bonds are hydrogenated by contact with molecular hydrogen in a liquid phase comprising a solution of a rhodium complex comprising (a) rhodium, (b) an anionic element or group, and (c) a compound of formula YR1R11R111, where Y is arsenic, antimony or phosphorus and the R's are the same or different hydrocarbon or substituted hydrocarbon groups or heterocyclic groups, the molar ratio of (a): (b): (c) being in the range 1:1:1 to 1:1:4. The rhodium complex may be of the type [RhX(YR1R11R111)2]n o RhH2X(YR1R11R111)3, or may be formed in situ from (RhXZ2)n and YR1R11R111, where in each case is the anionic element or group, and Z is a mono- or di-olefin. X may be cyanide, cyanate, carboxylate, SnCl3- or halogen, preferably chlorine. An inert solvent may be present. Compounds containing acetylenic bonds may be partially or completely hydrogenated as desired by controlling the hydrogen uptake. Compounds which may be hydrogenated include acrylonitrile and bicyclo[3,3,1]non-2-ene-9-one.
GB5275/66A 1966-02-07 1966-02-07 Hydrogenation process Expired GB1121643A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5275/66A GB1121643A (en) 1966-02-07 1966-02-07 Hydrogenation process
DE19671618529 DE1618529A1 (en) 1966-02-07 1967-02-07 Hydrogenation process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5275/66A GB1121643A (en) 1966-02-07 1966-02-07 Hydrogenation process

Publications (1)

Publication Number Publication Date
GB1121643A true GB1121643A (en) 1968-07-31

Family

ID=9793029

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5275/66A Expired GB1121643A (en) 1966-02-07 1966-02-07 Hydrogenation process

Country Status (2)

Country Link
DE (1) DE1618529A1 (en)
GB (1) GB1121643A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US5463154A (en) * 1992-05-12 1995-10-31 Exxon Chemical Patents Inc. Arsine and phosphines as acetylene converter moderators

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE435619C (en) * 1973-02-01 1985-11-18 Pfizer PROCEDURE FOR PREPARING A 6ALFA DEOXYTETRACYCLINE

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US5463154A (en) * 1992-05-12 1995-10-31 Exxon Chemical Patents Inc. Arsine and phosphines as acetylene converter moderators

Also Published As

Publication number Publication date
DE1618529B2 (en) 1973-11-15
DE1618529A1 (en) 1972-05-10

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