GB878120A - Improvements in the production of oligomers of 1, 3-dienes - Google Patents
Improvements in the production of oligomers of 1, 3-dienesInfo
- Publication number
- GB878120A GB878120A GB10236/60A GB1023660A GB878120A GB 878120 A GB878120 A GB 878120A GB 10236/60 A GB10236/60 A GB 10236/60A GB 1023660 A GB1023660 A GB 1023660A GB 878120 A GB878120 A GB 878120A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aluminium
- halide
- titanium
- titanium compound
- compound
- 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
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
-
- 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
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
Oligomers of 1,3-dienes are obtained by contacting the diene with (a) a ferric halide or a titanium compound and (b) aluminium and optionally (c) an aluminium halide and/or a compound which forms a complex with aluminium halides. Suitable dienes are butadiene, isoprene, 2,3 - dimethylbutadiene-1,3, cyclohexadiene - 1,3, hexadiene - 1,3 and 2-propylbutadiene-1,3; butadiene yields mainly cyclododecatriene-1,5,9. The titanium compound may be the tetramethylate, tetraethylate, tetrapropylate, tetrabutylate, trichloride, tribromide, tetrachloride, or tetrabromide, diethoxy titanium dichloride, triethoxy titanium chloride, bis-cyclopentadienyl titanium dichloride, or a dialkyl titanium dihalide. Aluminium is used as a dust or a powder of grain size 0.01-2 mm. Aluminium chloride, bromide or iodide may be added or formed in situ from the aluminium and the corresponding halide or hydrogen halide. Suitable complex forming compounds are aliphatic, araliphatic or aromatic ethers, or thiothers, amines, alkali or alkaline earth metal halides, hydrides or cyanides, and the salts of alkali, alkaline earth or earth (Al, Si, Y or La) metals with organic acids e.g. aliphatic acids containing up to 4 carbon atoms. The mol ratio of titanium compound: aluminium: aluminium halide may vary from 1:300:300 to 1:10:10 or the titanium compound may be in excess. The amount of complexing agent used may vary between wide limits but if used together with an aluminium halide preferably the mol ratio of combined titanium compound and aluminium halide to complexing agent should be from 1:0.2 to 1:3. A solvent may be added such as benzene, toluene, xylene, ethylbenzene, cumene, chlorbenzene, heptane, cyclohexane, isooctane or cyclododecatriene in amounts of 0.2 to 0.5 times the amount of diene. The catalyst may be "developed" in the solvent for up to 10 hours. Atmospheric pressure is preferred but the pressure may be lower or increased, e.g. to 10 atmospheres when using low boiling feeds, and temperatures of -50 to 150 DEG C. may be used.ALSO:Oligomers of 1,3-dienes are obtained by contacting the diene with (a) a ferric halide or a titanium compound and (b) aluminium and optionally (c) an aluminium halide and/or a compound which forms a complex with aluminium halides. The titanium compound may be the tetramethylate, tetraethylate, tetrapropylate, tetrabutylate, trichloride, tribromide, tetrachloride, or tetrabromide, diethoxy titanium dichloride, triethoxy titanium chloride, bis-cyclopentadienyl titanium dichloride, or a dialkyl titanium dihalide. Aluminium is used as a dust or a powder of grain size 0.01-2 mm. Aluminium chloride bromide or iodide may be added or formed in situ from the aluminium and the corresponding halide or hydrogen halide. Suitable complex forming compounds are aliphatic, araliphatic or aromatic ethers, or thioethers, amines, alkali or alkaline earth metal halides, hydrides or cyanides, and the salts of alkali, alkaline earth or earth (aluminium, scandium, yttrium or lanthanum) metals with organic acids e.g. aliphatic acids containing up to 4 carbon atoms. The mol ratio of titanium compound: aluminium: aluminium halide may vary from 1:300:300 to 1:10:10 or the titanium compound may be in excess. The amounting p of complexing agent used may vary between wide limits but if used together with an aluminium halide preferably the mol ratio of combined titanium compound and aluminium halide to complexing agent should be from 1:0.2 to 1:3. A solvent may be added such as benzene, toluene, xylene, ethylbenzene, cumene, chlorobenzene, heptane, cyclohexane, isooctane or cyclododecatriene in amounts of 0.2 to 0.5 times the amount of diene. The catalyst may be "developed" in the solvent for up to 10 hours.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE878120X | 1959-03-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB878120A true GB878120A (en) | 1961-09-27 |
Family
ID=6818363
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10236/60A Expired GB878120A (en) | 1959-03-24 | 1960-03-23 | Improvements in the production of oligomers of 1, 3-dienes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB878120A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3326990A (en) * | 1962-06-14 | 1967-06-20 | Columbian Carbon | Cycloolefin production using zieglertype reducing agent and a nickel chelate |
US3352839A (en) * | 1962-08-10 | 1967-11-14 | Goodrich Gulf Chem Inc | Diolefin polymerization catalysts using a metalliferous component, a catalyst regulator and aix |
US3356752A (en) * | 1965-05-18 | 1967-12-05 | Union Carbide Corp | Butadiene trimerization |
US3365507A (en) * | 1966-04-06 | 1968-01-23 | Du Pont | Cyclic oligomer recovery process |
CN112521247A (en) * | 2020-11-13 | 2021-03-19 | 万华化学集团股份有限公司 | Post-treatment method of cyclododecatriene reaction liquid |
-
1960
- 1960-03-23 GB GB10236/60A patent/GB878120A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3326990A (en) * | 1962-06-14 | 1967-06-20 | Columbian Carbon | Cycloolefin production using zieglertype reducing agent and a nickel chelate |
US3352839A (en) * | 1962-08-10 | 1967-11-14 | Goodrich Gulf Chem Inc | Diolefin polymerization catalysts using a metalliferous component, a catalyst regulator and aix |
US3356752A (en) * | 1965-05-18 | 1967-12-05 | Union Carbide Corp | Butadiene trimerization |
US3365507A (en) * | 1966-04-06 | 1968-01-23 | Du Pont | Cyclic oligomer recovery process |
CN112521247A (en) * | 2020-11-13 | 2021-03-19 | 万华化学集团股份有限公司 | Post-treatment method of cyclododecatriene reaction liquid |
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