DE1468708C - - Google Patents
Info
- Publication number
- DE1468708C DE1468708C DE19621468708 DE1468708A DE1468708C DE 1468708 C DE1468708 C DE 1468708C DE 19621468708 DE19621468708 DE 19621468708 DE 1468708 A DE1468708 A DE 1468708A DE 1468708 C DE1468708 C DE 1468708C
- Authority
- DE
- Germany
- Prior art keywords
- nickel
- metal
- compounds
- diolefins
- catalyst
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052987 metal hydride Inorganic materials 0.000 claims description 8
- 150000004681 metal hydrides Chemical class 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 6
- -1 nickel (II) compound Chemical class 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 3
- 239000002879 Lewis base Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- 150000007527 lewis bases Chemical class 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 claims 1
- 240000006240 Linum usitatissimum Species 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 241000158147 Sator Species 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims 1
- HOMQMIYUSVQSHM-UHFFFAOYSA-N cycloocta-1,3-diene;nickel Chemical group [Ni].C1CCC=CC=CC1.C1CCC=CC=CC1 HOMQMIYUSVQSHM-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000003574 free electron Substances 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- ZPFZQRQDUOHLJK-UHFFFAOYSA-N nickel;prop-2-enenitrile Chemical compound [Ni].C=CC#N.C=CC#N ZPFZQRQDUOHLJK-UHFFFAOYSA-N 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XRLIZCVYAYNXIF-HCHRGBFMSA-N (5E)-cyclododeca-1,3,5-triene Chemical compound C1CCC\C=C\C=CC=CCC1 XRLIZCVYAYNXIF-HCHRGBFMSA-N 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical class O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEST019833 | 1962-05-04 | ||
| DEST019833 | 1962-05-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1468708A1 DE1468708A1 (de) | 1969-05-08 |
| DE1468708C true DE1468708C (enrdf_load_stackoverflow) | 1973-04-12 |
Family
ID=7458363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621468708 Granted DE1468708A1 (de) | 1962-05-04 | 1962-05-04 | Verfahren zur Herstellung von cyclischen Di- bzw. Trimeren von 1,3-Diolefinen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1468708A1 (enrdf_load_stackoverflow) |
-
1962
- 1962-05-04 DE DE19621468708 patent/DE1468708A1/de active Granted
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH498061A (de) | Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-Diolefinen | |
| DE1223840B (de) | Verfahren zur Hydrierung von organischen Verbindungen | |
| DE1144268B (de) | Verfahren zur Herstellung von Cyclooctadien-(1, 5) aus Butadien | |
| DE1418672A1 (de) | Verfahren zur Herstellung von Oligomeren von 1,3-Dienen | |
| DE2032140A1 (de) | Katalysator, sowie dessen Anwendung bei der Polymerisation von ungesättigten Kohlenwasserstoffen | |
| DE1468708C (enrdf_load_stackoverflow) | ||
| DE2141186C3 (de) | Verfahren zur Herstellung primärer oder sekundärer, ungesättigter Ca u. C↓11↓- Alkohole | |
| DE2440954C2 (de) | Verfahren zur Herstellung von 2,6 Dimethyloctatrien- (1,3,6) | |
| DE2024093A1 (de) | Verfahren zur Herstellung von Katalysatoren sowie deren Anwendung bei der dimerisation und Codimerisation von Olefinen | |
| DE2902202A1 (de) | Sekundaere und tertiaere 2-carboxiethyl- und carboximethylphosphine und deren salze, verfahren zur herstellung sowie verwendung derselben | |
| DE1520964C3 (de) | Verfahren zur Oligomerisation von Olefinen | |
| DE1468708B (enrdf_load_stackoverflow) | ||
| DE1793718C3 (de) | Verfahren zur Cyclodimerisation von 1,3-Dfolefinen mittels aus kohlenoxydfreien Nickelverbindungen hergestellter Mischkatalysatoren | |
| DE1468271C3 (enrdf_load_stackoverflow) | ||
| WO2017178536A1 (de) | Katalysator zur hydroformylierung von olefinen und dessen verwendung | |
| DE2054009C3 (de) | Verfahren zur Äthylenpolymerisation | |
| DE1793718B2 (de) | Verfahren zur cyclodimerisation von 1,3-diolefinen mittels aus kohlenoxydfreien nickelverbindungen hergestellter mischkatalysatoren | |
| DE1953996C3 (de) | Verfahren zur Herstellung von Dialkenyltetrahydropyranen | |
| DE1643071C (enrdf_load_stackoverflow) | ||
| DE1288087B (de) | Verfahren zur Mischoligomerisation unter Verwendung von 1,3-Diolefinen in Gegenwart eines kohlenoxydfreien Organo-Metallkoinplexkatalysators der Übergangsmetalle der VIII. Nebengruppe | |
| DE1768213A1 (de) | Verfahren zur katalytischen Cyclo-Dimerisation von 1,3-Diolefinen | |
| DE1283836B (de) | Verfahren zur Herstellung von hauptsaechlich Cyclododekatrien-(1,5,9) enthaltenden Produkten durch Cyclooligomerisation von 1, 3-Diolefinen | |
| DE3027782A1 (de) | Verfahren zur oligomerisierung von ethylen | |
| DE2263882A1 (de) | Metallorganische olefinkomplexe salzartiger natur und verfahren zu deren herstellung | |
| DE1643071B1 (de) | Verfahren zur Cyclodimerisation von 1,3-Diolefinen |