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GB1121642A - New organic rhodium complexes and uses thereof - Google Patents

New organic rhodium complexes and uses thereof

Info

Publication number
GB1121642A
GB1121642A GB7077/65A GB707765A GB1121642A GB 1121642 A GB1121642 A GB 1121642A GB 7077/65 A GB7077/65 A GB 7077/65A GB 707765 A GB707765 A GB 707765A GB 1121642 A GB1121642 A GB 1121642A
Authority
GB
United Kingdom
Prior art keywords
rhcl
ph3p
prepared
olefine
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
GB7077/65A
Inventor
Robert Stevenson Coffey
Joseph Brian Smith
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
Priority to GB1934817A priority Critical patent/GB121642A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB7077/65A priority patent/GB1121642A/en
Priority to BE676669D priority patent/BE676669A/xx
Priority to NL6602062A priority patent/NL6602062A/xx
Priority to DE19661568817 priority patent/DE1568817A1/en
Priority to FR50156A priority patent/FR1468546A/en
Publication of GB1121642A publication Critical patent/GB1121642A/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
    • 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
    • B01J31/16—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
    • 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
    • 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
    • C07C5/02—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
    • C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to 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)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Hydrocarbons containing one or more olefinic or acetylenic bonds are hydrogenated using as catalyst a rhodium complex of formula RhX(R1R11R111Y)3 wherein X is an anion, Y is phosphorus, arsenic or antimony and R1, R11 and R111 are the same or different and are hydrocarbon, substituted hydrocarbon or heterocyclic groups. The process is preferably carried out in an inert solvent. Example 2 describes the hydrogenation of octene-1, octene-2, vinyl cyclohexene, cyclohexene and di-isobutylene to fully saturated products, and of phenyl acetylene to a mixture of styrene and ethyl benzene.ALSO:The invention comprises rhodium complexes of formula Rh(X)R1R11R111Y)3, wherein Y is phosphorus, arsenic or antimony, X is an anionic element or group and R1, R11 and R111 are the same or different and are hydrocarbon, substituted hydrocarbon (such as alkoxyaryl) or heterocyclic groups. They may generally be prepared by reacting a monovalent rhodium complex containing replaceable neutral ligands with YR1R11R111. The monovalent rhodium complex may for example be RhX(Ph3P)-(cyclo-1,5-octadiene) or preferably is a complex of formula (RhXZ2)n in which Z represents a mono-olefine and n is 2; or Z represents an acyclic conjugated di-olefine and n is 1. The particular compounds RhX(Ph3P)3 may also be prepared from the rhodium salt of X, by heating the rhodium salt with at least a four-fold molar excess of triphenyl phosphine in a suitable solvent. X, in the compounds may, for example, be a cyanide, cyanate, carboxylate or SnCl3- group but is suitably a halogen. The examples describe the preparation of RhCl(Ph3P)3, RhBr(Ph3P)3, RhI(Ph3P)3, RhCl(Ph2EtP)3, RhCl[(P-C6H4Cl)3P]3, and RhCl(Ph3A5)3. The compounds (RhXZ2)n above, when Z is a mono-olefine and X is chlorine, may be prepared by reacting RhCl3 in an alcohol solution with the mono-olefine. (RhCl(cyclo-octene)2)2 may be prepared in this way. When Z is an acyclic conjugated diolefine, the compounds may be prepared by digesting [RhCl(cyclooctene)2]2 with the appropriate diolefine. The invention also comprises a hydrogenation process comprising contacting a compound containing one or more olefinic or acetylenic bonds, and hydrogen with a rhodium complex of the invention. Propionitrile is formed in Example 2 by the hydrogenation of acrylonitrile, using as catalyst a compound of the invention.
GB7077/65A 1917-12-31 1965-02-18 New organic rhodium complexes and uses thereof Expired GB1121642A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB1934817A GB121642A (en) 1917-12-31 1917-12-31 Improvements in or relating to Refrigerating Machines.
GB7077/65A GB1121642A (en) 1965-02-18 1965-02-18 New organic rhodium complexes and uses thereof
BE676669D BE676669A (en) 1965-02-18 1966-02-17
NL6602062A NL6602062A (en) 1965-02-18 1966-02-17
DE19661568817 DE1568817A1 (en) 1965-02-18 1966-02-18 Hydrogenation process and process for the preparation of rhodium complexes useful as a catalyst therein
FR50156A FR1468546A (en) 1965-02-18 1966-02-18 Manufacturing process of rhodium complexes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7077/65A GB1121642A (en) 1965-02-18 1965-02-18 New organic rhodium complexes and uses thereof
GB4770265 1965-11-10

Publications (1)

Publication Number Publication Date
GB1121642A true GB1121642A (en) 1968-07-31

Family

ID=26241170

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7077/65A Expired GB1121642A (en) 1917-12-31 1965-02-18 New organic rhodium complexes and uses thereof

Country Status (5)

Country Link
BE (1) BE676669A (en)
DE (1) DE1568817A1 (en)
FR (1) FR1468546A (en)
GB (1) GB1121642A (en)
NL (1) NL6602062A (en)

Cited By (7)

* 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
CN102351914A (en) * 2011-10-25 2012-02-15 中国海洋石油总公司 Preparation method of tris(triphenylphosphine)rhodium chloride
CN102391312A (en) * 2011-10-25 2012-03-28 中国海洋石油总公司 Preparation method for palladium-tetrakis(triphenylphosphine) rhodium hydroxide
CN102408451A (en) * 2011-10-25 2012-04-11 中国海洋石油总公司 Preparation method of trans-carbonylchlorobis(triphenylphosphine)rhodium
PL422671A1 (en) * 2017-08-28 2019-03-11 Fundacja Uniwersytetu im. Adama Mickiewicza New anionic rhodium complexes, method for obtaining them and application, preferably for hydrosilylation processes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1326012A (en) * 1969-07-14 1973-08-08 Johnson Matthey Co Ltd Catalyst compositions
GB1368431A (en) * 1970-07-22 1974-09-25 Johnson Matthey Co Ltd Rhodium complex and methods of preparing the complex

Cited By (9)

* 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
CN102351914A (en) * 2011-10-25 2012-02-15 中国海洋石油总公司 Preparation method of tris(triphenylphosphine)rhodium chloride
CN102391312A (en) * 2011-10-25 2012-03-28 中国海洋石油总公司 Preparation method for palladium-tetrakis(triphenylphosphine) rhodium hydroxide
CN102408451A (en) * 2011-10-25 2012-04-11 中国海洋石油总公司 Preparation method of trans-carbonylchlorobis(triphenylphosphine)rhodium
CN102391312B (en) * 2011-10-25 2014-09-17 中国海洋石油总公司 Preparation method for palladium-tetrakis(triphenylphosphine) rhodium hydroxide
CN102351914B (en) * 2011-10-25 2014-11-05 中国海洋石油总公司 Preparation method of tris(triphenylphosphine)rhodium chloride
PL422671A1 (en) * 2017-08-28 2019-03-11 Fundacja Uniwersytetu im. Adama Mickiewicza New anionic rhodium complexes, method for obtaining them and application, preferably for hydrosilylation processes

Also Published As

Publication number Publication date
BE676669A (en) 1966-08-17
NL6602062A (en) 1966-08-19
FR1468546A (en) 1967-02-03
DE1568817A1 (en) 1970-04-16

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