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GB1105589A - Process for the production of cyclic olefines - Google Patents

Process for the production of cyclic olefines

Info

Publication number
GB1105589A
GB1105589A GB51233/65A GB5123365A GB1105589A GB 1105589 A GB1105589 A GB 1105589A GB 51233/65 A GB51233/65 A GB 51233/65A GB 5123365 A GB5123365 A GB 5123365A GB 1105589 A GB1105589 A GB 1105589A
Authority
GB
United Kingdom
Prior art keywords
silane
reacted
iii
halide
product
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
GB51233/65A
Inventor
Robert Arthur Lawrence Wilson
Leonard Keith Pugh
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 GB51233/65A priority Critical patent/GB1105589A/en
Publication of GB1105589A publication Critical patent/GB1105589A/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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • 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
    • B01J31/123—Organometallic polymers, e.g. comprising C-Si bonds in the main chain or in subunits grafted to the main chain
    • B01J31/124—Silicones or siloxanes or comprising such units
    • B01J31/126—Silicones or siloxanes or comprising such units the siloxanes or siloxane units, cyclic or not, comprising an additional Si-H bond, e.g. polyhydromethylsiloxane [PHMS]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/50—Diels-Alder conversion
    • C07C2/52—Catalytic processes
    • 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
    • B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
    • B01J2231/326—Diels-Alder or other [4+2] cycloadditions, e.g. hetero-analogues
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Methyl hydrogen polysiloxane is reacted with AlCl3 in cyclohexane solvent under an argon atmosphere and the product further reacted with TiCl4. The final product is used as a dimerization catalyst (see Division C5).ALSO:4-Vinyl cyclohexene and derivatives thereof are prepared by contacting an acyclic conjugated diene of formula C4X6, where each X is hydrogen or alkyl and the X's may be the same or different, in an anhydrous non-aromatic solvent with a catalyst comprising the reaction product of (i) a compound of B, Al, Ga, In or Tl, (ii) a silicon compound containing an Si-H bond, and (iii) a compound of a metal of Group IVa, Va or VIa of the Mendel<\>aeef Periodic Table. Catalyst component (i) is suitably a halide, an alkoxide, or a halogen alkoxide, AlCl3 being preferred; component (ii) is suitable a silane or siloxane, e.g. trimethyl silane, triethyl silane, dimethyl phenyl silane, methyl diphenyl silane, and a methyl hydrogen polysiloxane; and component (iii) is suitable a halide, oxyhalide, alcoholate or acetylacetonate, preferably TiCl4. All three catalyst components may be reacted together simultaneously, but preferably (i) and (ii) are first reacted together and the product reacted with (iii). The diene starting material may be butadiene, isoprene or piperylene, and suitable non-aromatic solvents are cycloalkanes, e.g. cyclohexane, and acyclic alkanes, e.g. a commercial mixture of C16- 18 alkanes. In the example, butadiene is converted to 4-vinyl cyclohexene.ALSO:Catalysts for cyclodimerisation of conjugated dienes (see Division C5) comprise the reaction product of (i) a compound of B, Al, Ga, In or Tl, e.g. a halide, alkoxide or halogen alkoxide (only AlCl3 specified), (ii) a silicon compound containing an Si-H bond, e.g. trimethyl silane, triethyl silane, dimethyl phenyl silane, methyl diphenyl silane, and a methyl hydrogen polysiloxane, and (iii) a compound of a metal of Group IVa, Va or VIa of the Mendeleef Periodic Table, e.g. a halide, oxyhalide, alcoholate or acetylacetone (only TiCl4 mentogether simultaneously but preferably (i) and tioned). All three components may be reacted (ii) are first reacted together and the product reacted with (iii). The reaction is carried out in an inert solvent under an inert gas atmosphere at 40-100 DEG C.
GB51233/65A 1965-12-02 1965-12-02 Process for the production of cyclic olefines Expired GB1105589A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB51233/65A GB1105589A (en) 1965-12-02 1965-12-02 Process for the production of cyclic olefines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB51233/65A GB1105589A (en) 1965-12-02 1965-12-02 Process for the production of cyclic olefines

Publications (1)

Publication Number Publication Date
GB1105589A true GB1105589A (en) 1968-03-06

Family

ID=10459168

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51233/65A Expired GB1105589A (en) 1965-12-02 1965-12-02 Process for the production of cyclic olefines

Country Status (1)

Country Link
GB (1) GB1105589A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4270016A (en) * 1979-06-01 1981-05-26 Tolstikov Genrikh A Method of preparing trans-, trans-, trans-1,5,9-cyclododecatriene
CN101885846A (en) * 2010-06-21 2010-11-17 陈俊光 Fabricating method of silicon oil gelation preparation elastomer

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4270016A (en) * 1979-06-01 1981-05-26 Tolstikov Genrikh A Method of preparing trans-, trans-, trans-1,5,9-cyclododecatriene
CN101885846A (en) * 2010-06-21 2010-11-17 陈俊光 Fabricating method of silicon oil gelation preparation elastomer
CN101885846B (en) * 2010-06-21 2012-01-25 陈俊光 Fabricating method of silicon oil gelation preparation elastomer

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