GB860377A - Process for the production of cyclododecatri-(1,5,9)-enes and other cyclic hydrocarbons - Google Patents
Process for the production of cyclododecatri-(1,5,9)-enes and other cyclic hydrocarbonsInfo
- Publication number
- GB860377A GB860377A GB26408/59A GB2640859A GB860377A GB 860377 A GB860377 A GB 860377A GB 26408/59 A GB26408/59 A GB 26408/59A GB 2640859 A GB2640859 A GB 2640859A GB 860377 A GB860377 A GB 860377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aluminium
- hydride
- trans
- aluminium hydride
- 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
Links
- 125000000753 cycloalkyl group Chemical group 0.000 title 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 8
- 229910000091 aluminium hydride Inorganic materials 0.000 abstract 8
- -1 Cyclic olefins Chemical class 0.000 abstract 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- 229910052987 metal hydride Inorganic materials 0.000 abstract 4
- 150000004681 metal hydrides Chemical class 0.000 abstract 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000005234 alkyl aluminium group Chemical group 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- AHXGRMIPHCAXFP-UHFFFAOYSA-L chromyl dichloride Chemical compound Cl[Cr](Cl)(=O)=O AHXGRMIPHCAXFP-UHFFFAOYSA-L 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 239000010936 titanium Substances 0.000 abstract 2
- 229910052719 titanium Inorganic materials 0.000 abstract 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 1
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
- 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
- C07C2527/132—Compounds comprising a halogen and chromium, molybdenum, tungsten or polonium
-
- 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
- C07C2531/12—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
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Cyclic olefins are prepared by the polymerization of butadiene, isoprene, or piperylene in the presence of a titanium or chromium halide and aluminium hydride or a complex metal hydride which is a complex of an alkali metal or alkaline earth metal hydride with aluminium hydride or an aluminium halide. The olefins formed from butadiene include vinylcyclohexene, cyclo-octadi-1,5-ene, cyclododecatri-1,5,9-ene, (trans, trans, trans and trans, trans, cis) and cyclohexadeca-tetra-1,5,9,13-ene; isoprene and piperylene form trimethylcyclododecatri - 1,5,9 - enes. The halide used may be titanium chloride or chromyl chloride. Complex hydrides which may be used include lithium and calcium aluminium hydrides. The aluminium hydride may be formed in situ from an alkyl aluminium dichloride and a dialkyl aluminium hydride or by reduction of aluminium chloride with a Group I or II metal hydride or lithium aluminium hydride. The reaction may be effected at -20 DEG to 150 DEG C., preferably at normal pressure, in an inert hydrocarbon or halohydrocarbon. Specifications 848,951 and 849,236 are referred to.ALSO:A catalyst for the polymerization of conjugated dienes to cyclic olefins comprises a titanium or chromium halide and aluminium hydride or a complex metal hydride formed from an alkali or alkaline earth metal hydride and an aluminium hydride or halide. Titanium tetrachloride and chromyl chloride are preferred and the aluminium hydride may be prepared in situ by reacting an alkyl aluminium dichloride with a dialkyl aluminium hydride or by reduction of aluminium chloride with a Group I or II metal hydride or lithium aluminium hydride. Specifications 848,951 and 849,236 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE860377X | 1958-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB860377A true GB860377A (en) | 1961-02-01 |
Family
ID=6791615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26408/59A Expired GB860377A (en) | 1958-08-06 | 1959-07-31 | Process for the production of cyclododecatri-(1,5,9)-enes and other cyclic hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB860377A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3844853A (en) * | 1963-06-21 | 1974-10-29 | Dow Chemical Co | Non-solvated aluminum hydride coated with stabilizer |
-
1959
- 1959-07-31 GB GB26408/59A patent/GB860377A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3844853A (en) * | 1963-06-21 | 1974-10-29 | Dow Chemical Co | Non-solvated aluminum hydride coated with stabilizer |
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