GB907698A - Production of oligomers of 1,3-dienes - Google Patents

Production of oligomers of 1,3-dienes

Info

Publication number
GB907698A
GB907698A GB971/61A GB97161A GB907698A GB 907698 A GB907698 A GB 907698A GB 971/61 A GB971/61 A GB 971/61A GB 97161 A GB97161 A GB 97161A GB 907698 A GB907698 A GB 907698A
Authority
GB
United Kingdom
Prior art keywords
aluminium
chloride
titanium
tetrachloride
zinc
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
GB971/61A
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 GB907698A publication Critical patent/GB907698A/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
    • C07C2/42—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • 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
    • 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
    • C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
    • 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
    • C07C2527/135—Compounds comprising a halogen and titanum, zirconium, hafnium, germanium, tin or lead
    • 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
    • C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Catalysts for the oligomerization of 1,3-dienes are obtained by mixing (a) an iron (III) halide or a titanium compound, (b) a metal of Group Ia, IIa, IIb, IIIa, IIIb, IVa, IVb, Vb or VIIb of the periodic system and (c) a halide of an element of Group IIb, IIIa, IVa or Va of the periodic system one of components (b) and (c) being aluminium or an aluminium halide. The titanium compound may be a titanium (IV) acid ester, titanium halide, titanium (IV) ester halide or organotitanium halide. Specified metals are lithium, sodium, potassium, beryllium, magnesium, calcium, strontium, barium, boron, aluminium, gallium, indium, thallium, lead, titanium, vanadium, manganese and cerium. Specified halides are boron trichloride, aluminium chloride, aluminium bromide, aluminium iodide, gallium bromide, indium chloride, thallium chloride, carbon tetrachloride, silicon tetrachloride, tin tetrachloride, zinc chloride, zinc iodide, cadmium chloride and antimony trichloride. The catalysts may also comprise substances which form complexes with the halides, e.g. aluminium chloride, zinc chloride, tin tetrachloride, antimony trichloride, alkali and alkaline earth metal halides, hydrides, cyanides and fatty acid salts, ethers, thioethers, amines and organic phosphines, many suitable compounds being listed. The catalysts are preferably aged before use, and may subsequently be destroyed by adding water, methanol, ethanol or acetone. Specification 878,120 is referred to.ALSO:1,3-Dienes are oligomerised by reacting in the presence of a catalyst formed by mixing (a) an iron (III) halide or a titanium compound, (b) a metal of Group Ia, IIa, IIb, IIIa, IIIb, IVa, IVb, Vb or VIIb of the Periodic System and (c) a halide of an element of Group IIb, IIIa, IVa or Va of the Periodic System one of components (b) and (c) being aluminium or an aluminium halide. Specified dienes are butadiene, isoprene, 2,3-dimethyl butadiene and cyclohexadiene-1,3. The process may be effected batchwise or continuously, in the presence of liquid media, e.g. benzene, toluene, xylene, ethyl benzene, cumene, chlorobenzene, heptane, cyclohexane, isooctane or cyclododecatriene-1,5,9. The catalysts may also comprise substances which form complexes with halogen compounds, e.g. aluminium chloride, zinc chloride, tin tetrachloride, antimony trichloride, alkali and alkaline earth metal halides, hydrides, cyanides and fatty acid salts, ethers, thioethers, amines and organic phosphines. Many suitable catalyst forming components are specified and examples describe the oligomerisation of butadiene in the presence of catalysts formed from (1) titanium tetrachloride, zinc and aluminium trichloride, tribromide and triiodide using as complexing agents anisol, lithium chloride, potassium iodide, magnesium iodide, sodium hydride, diphenylene oxide, quinoline, triphenyl phosphine and diethyl ether; (2) titanium tri- or tetrachloride, aluminium, zinc chloride and sodium chloride; titanium tetrachloride and aluminium chloride with (3) sodium and sodium chloride, (4) beryllium, (5) magnesium, (6) calcium, (8) gallium and sodium chloride, (9) lead and sodium chloride, (12) cerium, (16) cadmium, (18) tin and sodium chloride, (19) manganese and diphenylene sulphide, (20) an aluminium/vanadium alloy and sodium chloride, and (25) lithium, magnesium and sodium chloride; titanium tetrachloride and aluminium with (7) carbon tetrachloride and sodium chloride, (10) tin tetrachloride and sodium chloride, (11) antimony trichloride, (14) boron trichloride, (15) bismuth trichloride, and (17) silicon tetrachloride and sodium chloride; (13) titanium tetrachloride, zinc and aluminium tribromide; aluminium chloride and sodium chloride with (21) titanium tetrabromide and titanium, (22) diethoxy dichloro titanium and zinc, (23) titanium tetrafluoride and zinc, (24) ferric chloride and aluminium, and (27) C6H5TiCl2.2AlCl3 and zinc; and the oligomerisation of isoprene in the presence of a catalyst formed from (26) titanium tetrachloride, aluminium and carbon tetrachloride. The products may be cyclic, polycyclic and open chain compounds and include cyclododecatriene - 1,5,9, cyclooctadiene - 1,5, 1 - vinyl hexene-3 and other oligomers containing 3, 6 and 8 butadiene units. Specification 878,120 is referred to.
GB971/61A 1960-01-13 1961-01-10 Production of oligomers of 1,3-dienes Expired GB907698A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB56218A DE1106758B (en) 1960-01-13 1960-01-13 Process for the preparation of cyclododecatrienes (1, 5, 9) and higher-molecular oligomers from 1, 3-dienes

Publications (1)

Publication Number Publication Date
GB907698A true GB907698A (en) 1962-10-10

Family

ID=6971250

Family Applications (1)

Application Number Title Priority Date Filing Date
GB971/61A Expired GB907698A (en) 1960-01-13 1961-01-10 Production of oligomers of 1,3-dienes

Country Status (3)

Country Link
DE (1) DE1106758B (en)
DK (1) DK106277C (en)
GB (1) GB907698A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1179934B (en) * 1964-10-22 Hans J. Zimmer Verfahrenstechnik, Frankfurt/M Process for the preparation of cyclododecatriene- (l, 5,9)
DE1137007B (en) * 1960-08-18 1962-09-27 Basf Ag Process for the preparation of lower, liquid oligomers from 1,3-dienes
DE1155443B (en) * 1961-09-21 1963-10-10 Basf Ag Process for the continuous production of cyclododecatrienes (1, 5, 9) from 1, 3-dienes
DE1165590C2 (en) * 1962-06-07 1974-08-29 Bayer Ag Process for the preparation of liquid, cyclic oligomers of 1,3-dienes
DE1212075B (en) * 1963-03-08 1966-03-10 Huels Chemische Werke Ag Process for processing cis, trans, trans-cyclododecatriene (1, 5, 9)
CN102872916B (en) * 2012-09-01 2014-11-05 万华化学集团股份有限公司 Composite catalyst, preparation method of composite catalyst and method of catalyzing butadiene trimerization reaction with composite catalyst

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1050333B (en) * 1956-02-23 1959-02-12 Studiengesellschaft Kohle Mbh Process for the preparation of cyclododecatrienes (1,5,9) among other annular hydrocarbons
DE1043329B (en) * 1957-01-31 1958-11-13 Studiengesellschaft Kohle Mbh Process for the production of cyclododecatrienes (1, 5, 9) among other ring-shaped hydrocarbons
DE1056123B (en) * 1957-04-17 1959-04-30 Studiengesellschaft Kohle Mbh Process for the production of cyclododecatrienes (1, 5, 9) among other ring-shaped hydrocarbons

Also Published As

Publication number Publication date
DE1106758B (en) 1961-05-18
DK106277C (en) 1967-01-16

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