DE2617403C3 - Verfahren zur Herstellung von Polyolefinölen - Google Patents
Verfahren zur Herstellung von PolyolefinölenInfo
- Publication number
- DE2617403C3 DE2617403C3 DE2617403A DE2617403A DE2617403C3 DE 2617403 C3 DE2617403 C3 DE 2617403C3 DE 2617403 A DE2617403 A DE 2617403A DE 2617403 A DE2617403 A DE 2617403A DE 2617403 C3 DE2617403 C3 DE 2617403C3
- Authority
- DE
- Germany
- Prior art keywords
- oils
- dicarbonyl compound
- aluminum
- aluminum halide
- 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
- 239000003921 oil Substances 0.000 title claims description 23
- 229920000098 polyolefin Polymers 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 dicarbonyl compound Chemical class 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 24
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- 150000001336 alkenes Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 150000001350 alkyl halides Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 10
- 239000010687 lubricating oil Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 238000010538 cationic polymerization reaction Methods 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 239000012208 gear oil Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- PFENPVAFZTUOOM-UHFFFAOYSA-N phenyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1=CC=CC=C1 PFENPVAFZTUOOM-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Cosmetics (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50049004A JPS51124186A (en) | 1975-04-22 | 1975-04-22 | Preparation of liquid olefin polymer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2617403A1 DE2617403A1 (de) | 1976-11-04 |
| DE2617403B2 DE2617403B2 (de) | 1981-09-17 |
| DE2617403C3 true DE2617403C3 (de) | 1982-05-19 |
Family
ID=12819019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2617403A Expired DE2617403C3 (de) | 1975-04-22 | 1976-04-21 | Verfahren zur Herstellung von Polyolefinölen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4006199A (enExample) |
| JP (1) | JPS51124186A (enExample) |
| DE (1) | DE2617403C3 (enExample) |
| GB (1) | GB1481947A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5814408B2 (ja) * | 1977-08-31 | 1983-03-18 | ライオン株式会社 | オレフイン重合体の製造法 |
| JPS5968397A (ja) * | 1982-10-13 | 1984-04-18 | Cosmo Co Ltd | リヤアクスル用ギヤ油組成物 |
| US5196635A (en) * | 1991-05-13 | 1993-03-23 | Ethyl Corporation | Oligomerization of alpha-olefin |
| FR2693455B1 (fr) * | 1992-07-09 | 1994-09-30 | Inst Francais Du Petrole | Procédé de fabrication d'oléfines alpha légères par oligomérisation de l'éthylène. |
| FR2715154B1 (fr) * | 1994-01-14 | 1996-04-05 | Inst Francais Du Petrole | Procédé de production d'oléfines alpha légères de pureté améliorée par oligomérisation, de l'éthylène. |
| WO2002088205A2 (en) * | 2001-04-27 | 2002-11-07 | Honam Petrochemical Corporation | Method for preparing polyalphaolefin from 1-octene |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1520900C3 (de) * | 1963-12-30 | 1978-07-13 | Mobil Oil Corp., New York, N.Y. (V.St.A.) | Verfahren zum Polymerisieren von Olefinen |
| US3842134A (en) * | 1972-06-09 | 1974-10-15 | Bray Oil Co | Polymerization process |
| JPS5414083B2 (enExample) * | 1974-01-29 | 1979-06-05 | ||
| JPS5320003B2 (enExample) * | 1974-02-22 | 1978-06-24 |
-
1975
- 1975-04-22 JP JP50049004A patent/JPS51124186A/ja active Granted
-
1976
- 1976-04-15 US US05/677,158 patent/US4006199A/en not_active Expired - Lifetime
- 1976-04-20 GB GB15917/76A patent/GB1481947A/en not_active Expired
- 1976-04-21 DE DE2617403A patent/DE2617403C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5545046B2 (enExample) | 1980-11-15 |
| US4006199A (en) | 1977-02-01 |
| GB1481947A (en) | 1977-08-03 |
| DE2617403B2 (de) | 1981-09-17 |
| JPS51124186A (en) | 1976-10-29 |
| DE2617403A1 (de) | 1976-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2702604C2 (de) | Polyisobutene | |
| EP0628575B1 (de) | Verfahren zur Herstellung hochreaktiver Polyisobutene | |
| DE2904314A1 (de) | Verfahren zur herstellung von polyisobutenen | |
| DE2930108A1 (de) | Verfahren zur herstellung von weitgehend amorphen buten-l-propen-ethen-terpolymeren mit hohem erweichungspunkt | |
| DE2616146A1 (de) | Verfahren zur herstellung von olefinoligomeren | |
| DE2837235C2 (de) | Verfahren zur Herstellung von Olefinoligomeren und dabei verwendeter Katalysator | |
| DE2617403C3 (de) | Verfahren zur Herstellung von Polyolefinölen | |
| DE2708010A1 (de) | Verfahren zur polymerisation von aethylen | |
| DE2064206C2 (de) | Verfahren zur Herstellung von synthetischen Schmierölen durch Polymerisation von α-Olefin-Fraktionen | |
| DE2633745A1 (de) | Verfahren zur herstellung von polyolefinoelen | |
| DE2409968C3 (de) | Verfahren zur Herstellung eines synthetischen Schmieröls | |
| DE1520900C3 (de) | Verfahren zum Polymerisieren von Olefinen | |
| DE2855421A1 (de) | Weichmacher | |
| DE867992C (de) | Verfahren zur Umwandlung von AEthylenhomologen in oelige oder hoehermolekulare Erzeugnisse durch Polymerisation | |
| DE2507390A1 (de) | Verfahren zur herstellung von fluessigen kohlenwasserstoffpolymeren | |
| EP0270001A2 (de) | Verfahren zur Herstellung von Decenoligomeren und deren Verwendung als Schmieröle | |
| DE948088C (de) | Verfahren zur Herstellung von Corpolymerisaten | |
| DE2718771A1 (de) | Katalysator zur polymerisation von monoolefinen und verfahren zu seiner herstellung | |
| DE2552337C3 (de) | Verfahren zur Herstellung flüssiger Polyolefine | |
| DE1520887C3 (de) | Verfahren zur Herstellung eines synthetischen Schmieröls | |
| DE2411496C2 (de) | Verfahren zur Herstellung von flüssigen Polymeren mit sehr hoher Viskosität | |
| DE2602554A1 (de) | Verfahren zur herstellung von olefinoligomeren | |
| DE1217945B (de) | Verfahren zur Herstellung von synthetischen Schmieroelen | |
| DE1443477C (de) | Verfahren zur Ohgomerisierung von alpha Olefinen | |
| EP0041157A2 (de) | Verfahren zur Homo- und Mischpolymerisation von alpha-Olefinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8227 | New person/name/address of the applicant |
Free format text: LION CORP., TOKYO, JP |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |