GB987423A - Production of oligomers of 1,3-dienes - Google Patents

Production of oligomers of 1,3-dienes

Info

Publication number
GB987423A
GB987423A GB2500962A GB2500962A GB987423A GB 987423 A GB987423 A GB 987423A GB 2500962 A GB2500962 A GB 2500962A GB 2500962 A GB2500962 A GB 2500962A GB 987423 A GB987423 A GB 987423A
Authority
GB
United Kingdom
Prior art keywords
compound
aluminium
organo
catalyst
halide
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
GB2500962A
Inventor
Hans Lautenschlager
Emil Scharf
Dietmar Wittenberg
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
Priority claimed from DEB63096A external-priority patent/DE1152408B/en
Priority claimed from DEB64079A external-priority patent/DE1155443B/en
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB987423A publication Critical patent/GB987423A/en
Expired legal-status Critical Current

Links

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
    • C07C2/50—Diels-Alder conversion
    • C07C2/52—Catalytic processes
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Oligomers of 1,3-dienes, particularly cyclic olefins, are obtained in the presence of a catalyst containing titanium, chromium, iron or nickel which has been activated prior to the reaction with an olefinic, polyolefinic or acetylenic compound. The catalyst may comprise a chromium halide and an organo-aluminium compound (Specification 849,236), chromium oxide, an acid chloride, amide or anhydride and an organo-aluminium compound (Specification 878,650), a titanium compound and an organo-aluminium compound (Specifications 848,951, 867,017, 860,377 and 892,759), a titanium compound or ferric halide, a metal of Group Ia, IIa, IIb, IIIb, IVa, IVb, Vb or VIIb and a halide of an element of Group IIb, IIIa, IVa or Va, the presence of aluminium or an aluminium halide being essential (Specifications 878,120 and 907,698), and a nickel compound, an organo-metallic compound or metallic hydride and a phosphine or phosphite (Belgian Specification 598,363). The activating compound may be a hydrocarbon or contain inert groups such as ether, carboxylic ester, nitrile, carboxylic amide, amine, imine, epoxy, aldehyde, ketone or sulphide groups, many being specified, but the preferred compound is the diene to be oligomerized. This is preferably butadiene; also specified are isoprene, 2,3-dimethylbutadiene, 2-ethylbutadiene, pentadiene-1,3 hexadiene - 2,4,3 - methyl - heptatriene-1,4,6 and octatriene-1,3,6. The activating compound is used in an amount to give a molar ratio to the titanium, chromium, iron or nickel of at least 1:1 and preferably in sufficient excess to form a solvent; alternatively an extraneous solvent, particularly a hydrocarbon or ether, is added. The activator may be added to the formed catalyst or the catalyst may be formed in the presence of the activator. Solid constituents of the formed catalyst may be removed if desired. Oligomerization is effected at - 50 DEG to 150 DEG C. and preferably under pressure if the diene is gaseous. Specification 935,716 also is referred to.ALSO:Oligomers of 1,3-dienes, particularly cyclic olefins, are obtained in the presence of a catalyst containing titanium, chromium, iron or nickel which has been activated prior to the reaction with an olefinic, polyolefinic or acetylenic compound. The catalyst may comprise a chromium halide and an organo-aluminium compound (Specification 849,236), chromium oxide, an acid chloride, amide or anhydride and an organo-aluminium compound (Specification 878,650), a titanium compound and an organo-aluminium compound (Specifications 848,951, 867,017, 860,377 and 892,759), a titanium compound or ferric halide, a metal of Group IA, IIA, IIB, IIIB, IVA, IVB, VB or VIIB and a halide of an element of Group IIB, IIIA, IVA or VA, the presence of aluminium or an aluminium halide being essential (Specifications 878,120 and 907,698), and a nickel compound, an organo-metallic compound or metallic hydride and a phosphine or phosphite (Belgian Specification 598,363). The activating compound may be a hydrocarbon or contain inert groups such as ether, carboxylic ester, nitrile, carboxylic amide, amine, imine, epoxy, aldehyde, ketone or sulphide groups, many being specified, but the preferred compound is the diene to be oligomerized. This is preferably butadiene; also specified are isoprene, 2,3-dimethylbutadiene; 2-ethylbutadiene, pentadiene-1,3, hexadiene-2,4, 3-methyl-heptatriene-1,4,6 and octatriene-1,3,6. The activating compound is used in an amount to give a molar ratio to the titanium, chromium, iron or nickel of at least 1:1 and preferably in sufficient excess to form a solvent; alternatively an extraneous solvent, particularly a hydrocarbon or ether, is added. The activator may be added to the formed catalyst or the catalyst may be formed in the presence of the activator. Solid constituents of the formed catalyst may be removed if desired. Oligomerization is effected at -50 DEG C. to 150 DEG C. and preferably under pressure if the diene is gaseous. Specification 935,716 also is referred to.
GB2500962A 1961-06-30 1962-06-29 Production of oligomers of 1,3-dienes Expired GB987423A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEB63096A DE1152408B (en) 1961-06-30 1961-06-30 Process for the continuous production of cyclododecatrienes (1, 5, 9) from 1, 3-dienes
DEB0063166 1961-07-06
DEB64079A DE1155443B (en) 1961-09-21 1961-09-21 Process for the continuous production of cyclododecatrienes (1, 5, 9) from 1, 3-dienes

Publications (1)

Publication Number Publication Date
GB987423A true GB987423A (en) 1965-03-31

Family

ID=27209153

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2500962A Expired GB987423A (en) 1961-06-30 1962-06-29 Production of oligomers of 1,3-dienes

Country Status (1)

Country Link
GB (1) GB987423A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3376355A (en) * 1965-02-12 1968-04-02 Stamicarbon Preparation of 1, 5, 9-cyclododecatriene
US3381045A (en) * 1965-06-29 1968-04-30 Du Pont Cyclododecatriene 1, 5, 9 process
US3414629A (en) * 1965-05-13 1968-12-03 Eastman Kodak Co Cyclooligomerization

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3376355A (en) * 1965-02-12 1968-04-02 Stamicarbon Preparation of 1, 5, 9-cyclododecatriene
US3414629A (en) * 1965-05-13 1968-12-03 Eastman Kodak Co Cyclooligomerization
US3381045A (en) * 1965-06-29 1968-04-30 Du Pont Cyclododecatriene 1, 5, 9 process

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