GB872348A - A process for the production of oligomers of 1,3-dienes - Google Patents

A process for the production of oligomers of 1,3-dienes

Info

Publication number
GB872348A
GB872348A GB43647/59A GB4364759A GB872348A GB 872348 A GB872348 A GB 872348A GB 43647/59 A GB43647/59 A GB 43647/59A GB 4364759 A GB4364759 A GB 4364759A GB 872348 A GB872348 A GB 872348A
Authority
GB
United Kingdom
Prior art keywords
aluminium
chloride
anhydride
diethyl
trans
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
GB43647/59A
Inventor
Herbert Mueller
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB872348A publication Critical patent/GB872348A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
    • C07C2/44—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion of conjugated dienes only
    • C07C2/46—Catalytic processes
    • C07C2/465—Catalytic processes with hydrides or organic compounds
    • 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
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/38—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
    • C07C2/40—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes of conjugated dienes
    • C07C2/403—Catalytic processes
    • C07C2/406—Catalytic processes with hydrides or organic compounds
    • 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
    • C07C2527/08—Halides
    • 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
    • C07C2531/14—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

Cyclic olefines and other liquid oligomers are obtained by contacting a 1,3-diolefine with a catalyst comprising (a) chromium (vi) oxide (b) an organic or inorganic acid halide or an organic acid anhydride or amide and (c) a trihydrocarbonyl aluminium or dihydrocarbonyl aluminium hydride. Suitable molar ratios of the three constituents are (a):(b) between 1:3 and 3:1 and (a):(c) between 1:2 and 1:15, and a total amount of 0.5-10% by weight of diolefine is used. Specified compounds (b) are acetyl chloride, propionyl chloride, butyric acid chloride, stearic acid chloride, benzoyl chloride, adipic acid chloride, phosphorus trichloride, phosphorus oxychloride, thionyl chloride, acetic anhydride, propionic anhydride, succinic anhydride, glutaric anhydride, N,N-dimethyl formamide, N,N-diethyl formamide, N,N-dibutyl formamide, N-formyl pyrrolidine, N,N-diethyl acetamide, N,N-dimethyl propionamide, N-methyl pyrrolidone and N-methyl caprolactam. The compound (c) may be aluminium triphenyl, diethyl aluminium hydride, dipropyl aluminium hydride, di-iosbutyl aluminium hydride, aluminium triethyl, aluminium triisobutyl, aluminium tri-n-butyl and aluminium tripopyl. The 1,3- diolefine may be 1,3-butadiene, which produces cyclooctadiene1,5, 1-vinylcyclohexene-3, cyclododecatriene1,5-9 (trans, trans, trans and trans, trans, cis) and higher unsaturated oligomers, isoprene, which produces isomeric trimethylcyclododecatrienes - 1,5,9,2,3- dimethylbutadiene - 1,3 which produces a trimer, probably 2,3,6,7,10, 11-hexamethyl-dodecatetraene-1,5,7,11, piperylene, which also p produces trimethylcyclododecatrienes-1,5,9, and cyclohexadiene-1,3, which produces a bicyclic dimer. An inert solvent is preferably present which may be a hydrocarbon or chlorinated hydrocarbon and the reaction is effected at -50 to 150 DEG C. Increased pressure may be necessary to maintain the liquid phase.ALSO:A catalyst for polymerizing diolefines to cyclic olefines comprises (a) chromium (VI) oxide, (b) an organic or inorganic acid halide or an organic acid anhydride or amide (preferably substituted twice at the nitrogen atom and including lactams) and (c) a trihydrocarbonyl aluminium or dihydrocarbonyl aluminium hydride. Suitable molar ratios of (a) to (b) are from 1:3 to 3:1 and of (a) to (c) from 1:2 to 1:15. Specified for (b) are acetyl chloride, propionyl chloride, butyric acid chloride, stearic acid chloride, benzoyl chloride, adipic acid chloride, phosphorus tri-chloride, phosphorus oxychloride, thionyl chloride, acetic anhydride, propionic anhydride, succinic anhydride, glutaric anhydride, N,N-dimethyl-, -diethyl-, or -dibutylformamide, N-formyl pyrrolidine, N,N-diethyl acetamide, N,N-dimethyl propionamide, N-methyl pyrrolidone and N-methyl caprolactam. Compound (c) may be aluminium triphenyl, diethyl-, dipropyl- or di-isobutylaluminium hydride, or aluminium-triethyl, -tri-isobutyl, -tri-n-butyl or -tripropyl. The catalyst is preferably prepared by treating the chromium oxide with the acid derivative in the presence of an inert hydrocarbon or chlorinated hydrocarbon, e.g. in a ball mill, for 1-10 hours, and then adding the aluminium compound.
GB43647/59A 1958-12-27 1959-12-23 A process for the production of oligomers of 1,3-dienes Expired GB872348A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE872348X 1958-12-27

Publications (1)

Publication Number Publication Date
GB872348A true GB872348A (en) 1961-07-05

Family

ID=6815993

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43647/59A Expired GB872348A (en) 1958-12-27 1959-12-23 A process for the production of oligomers of 1,3-dienes

Country Status (1)

Country Link
GB (1) GB872348A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231627A (en) * 1962-02-23 1966-01-25 Copolymer Rubber & Chem Corp Process for preparing cyclododecatrienes and catalyst therefor
US3326990A (en) * 1962-06-14 1967-06-20 Columbian Carbon Cycloolefin production using zieglertype reducing agent and a nickel chelate

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231627A (en) * 1962-02-23 1966-01-25 Copolymer Rubber & Chem Corp Process for preparing cyclododecatrienes and catalyst therefor
US3326990A (en) * 1962-06-14 1967-06-20 Columbian Carbon Cycloolefin production using zieglertype reducing agent and a nickel chelate

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