GB944574A - Improvements in cycloolefin production - Google Patents
Improvements in cycloolefin productionInfo
- Publication number
- GB944574A GB944574A GB1942261A GB1942261A GB944574A GB 944574 A GB944574 A GB 944574A GB 1942261 A GB1942261 A GB 1942261A GB 1942261 A GB1942261 A GB 1942261A GB 944574 A GB944574 A GB 944574A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diene
- compound
- phenyl
- catalyst
- phenyldiolefines
- 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
- 150000001925 cycloalkenes Chemical class 0.000 title 1
- -1 acyclic diene Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 1
- LIFLRQVHKGGNSG-UHFFFAOYSA-N 2,3-dichlorobuta-1,3-diene Chemical compound ClC(=C)C(Cl)=C LIFLRQVHKGGNSG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000002904 solvent Substances 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
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cyclic polyolefines are obtained by polymerizing a conjugated acyclic diene at 40-250 DEG C. in the presence of a compound of the formula [Rx(RO)3-xZ]3NiCO, or mixtures of such compounds where each R is the same or different organic radical, x is 0, 1, 2 or 3 and Z is P, As or Sb. The diene may be butadiene or a derivative thereof, e.g. isoprene, piperylene, phenyldiolefines, chloroprene, 2,3-dichlorobutadiene and 2,3-dimethylbutadiene, the products being 4-vinylcyclohexene, octadiene-1,5 and cyclodecatriene-1,5,9, or the corresponding derivatives. In the catalyst, the group R may be methyl, ethyl, propyl, butyl, hexyl, dodecyl, isooctyl, isobutyl, isopentyl, cyclopentyl, cyclohexyl, cyclooctyl, phenyl, biphenyl, a - or b -naphthyl, p-chlorophenyl, 2-chloroethyl, m-(trifluoromethyl) phenyl, bromocyclohexyl, m-, o-, or p-tolyl, 3,5-xylyl, p-methoxyphenyl, p-acetophenyl or a heterocyclic compound. The catalyst may be mixed with the corresponding compound [Rx(RO)3Z]2Ni(CO)2 and is used in amounts of 0.001-10% by weight of the diene. The reaction may be effected in a hydrocarbon solvent for 0.05-2 hours.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5083660A | 1960-08-22 | 1960-08-22 | |
| US8476661A | 1961-01-25 | 1961-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB944574A true GB944574A (en) | 1963-12-18 |
Family
ID=26728741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1942261A Expired GB944574A (en) | 1960-08-22 | 1961-05-30 | Improvements in cycloolefin production |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1298526B (en) |
| GB (1) | GB944574A (en) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686208A (en) * | 1950-09-12 | 1954-08-10 | Ici Ltd | Production of cyclo-olefinic compounds |
| DE881511C (en) * | 1950-09-12 | 1953-06-29 | Ici Ltd | Process for the preparation of cycloolefins with at least 8 carbon atoms in the ring |
| US2686209A (en) * | 1951-11-19 | 1954-08-10 | Ici Ltd | Production of cyclo-olefinic compounds |
| DE951213C (en) * | 1951-11-19 | 1956-10-25 | Ici Ltd | Process for the production of cycloocta-1, 5-diene by dimerizing butadiene |
| DE1050333B (en) * | 1956-02-23 | 1959-02-12 | Studiengesellschaft Kohle Mbh | Process for the preparation of cyclododecatrienes (1,5,9) among other annular hydrocarbons |
| DE1085523B (en) * | 1958-08-06 | 1960-07-21 | Studiengesellschaft Kohle Mbh | Process for the production of cyclododecatrienes (1, 5, 9) among other ring-shaped hydrocarbons |
| DE1086226B (en) * | 1959-03-10 | 1960-08-04 | Studiengesellschaft Kohle Mbh | Process for the preparation of cyclododecatriene (1, 5, 9) |
-
1961
- 1961-05-30 GB GB1942261A patent/GB944574A/en not_active Expired
- 1961-05-30 DE DE1961C0024238 patent/DE1298526B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1298526B (en) | 1969-07-03 |
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