WO2024080214A1 - PROCÉDÉ DE PRODUCTION DE POLYMÈRE D'α-OLÉFINE - Google Patents
PROCÉDÉ DE PRODUCTION DE POLYMÈRE D'α-OLÉFINE Download PDFInfo
- Publication number
- WO2024080214A1 WO2024080214A1 PCT/JP2023/036302 JP2023036302W WO2024080214A1 WO 2024080214 A1 WO2024080214 A1 WO 2024080214A1 JP 2023036302 W JP2023036302 W JP 2023036302W WO 2024080214 A1 WO2024080214 A1 WO 2024080214A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- olefin
- olefin polymer
- producing
- group
- compound
- Prior art date
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- 239000004711 α-olefin Substances 0.000 title claims abstract description 197
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 144
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 239000000178 monomer Substances 0.000 claims abstract description 60
- 239000002994 raw material Substances 0.000 claims abstract description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 56
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 238000002156 mixing Methods 0.000 claims abstract description 25
- 150000008040 ionic compounds Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 17
- 150000001298 alcohols Chemical class 0.000 claims abstract description 13
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 13
- 150000002989 phenols Chemical class 0.000 claims abstract description 10
- 150000001768 cations Chemical class 0.000 claims abstract description 9
- 150000002170 ethers Chemical class 0.000 claims abstract description 9
- -1 tetraphenylborate salt Chemical class 0.000 claims description 83
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 62
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 61
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 229940069096 dodecene Drugs 0.000 claims description 27
- 150000002430 hydrocarbons Chemical group 0.000 claims description 21
- 239000010687 lubricating oil Substances 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 230000000737 periodic effect Effects 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 6
- 239000006078 metal deactivator Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000002518 antifoaming agent Substances 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 19
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000314 lubricant Substances 0.000 description 10
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 6
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 6
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 6
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 6
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 6
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 6
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 6
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 5
- OMXANELYEWRDAW-UHFFFAOYSA-N 1-Hexacosene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=C OMXANELYEWRDAW-UHFFFAOYSA-N 0.000 description 4
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007848 Bronsted acid Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- YYLACZAXCCJCJO-UHFFFAOYSA-N heptacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC=C YYLACZAXCCJCJO-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- UBMJSQAFNUWJEG-UHFFFAOYSA-N nonacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC=C UBMJSQAFNUWJEG-UHFFFAOYSA-N 0.000 description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- ZDLBWMYNYNATIW-UHFFFAOYSA-N tetracos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCC=C ZDLBWMYNYNATIW-UHFFFAOYSA-N 0.000 description 4
- WMZHDICSCDKPFS-UHFFFAOYSA-N triacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C WMZHDICSCDKPFS-UHFFFAOYSA-N 0.000 description 4
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910018287 SbF 5 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- JTOGFHAZQVDOAO-UHFFFAOYSA-N henicos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCC=C JTOGFHAZQVDOAO-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- 150000002738 metalloids Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QEXZDYLACYKGOM-UHFFFAOYSA-N octacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC=C QEXZDYLACYKGOM-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- BDWBGSCECOPTTH-UHFFFAOYSA-N pentacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC=C BDWBGSCECOPTTH-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 239000005844 Thymol Substances 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 1
- 229940028820 didecyl ether Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 1
- SKNCDRJPFBIAGA-UHFFFAOYSA-N diphenylarsane Chemical group C=1C=CC=CC=1[AsH]C1=CC=CC=C1 SKNCDRJPFBIAGA-UHFFFAOYSA-N 0.000 description 1
- UCLOAJGCFQIQQW-UHFFFAOYSA-N diphenylboron Chemical group C=1C=CC=CC=1[B]C1=CC=CC=C1 UCLOAJGCFQIQQW-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- GNTRBBGWVVMYJH-UHFFFAOYSA-M fluoro(dimethyl)alumane Chemical compound [F-].C[Al+]C GNTRBBGWVVMYJH-UHFFFAOYSA-M 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- IPFASKMZBDWRNG-UHFFFAOYSA-N manganese 5,10,15,20-tetraphenyl-21,23-dihydroporphyrin Chemical compound [Mn].c1cc2nc1c(-c1ccccc1)c1ccc([nH]1)c(-c1ccccc1)c1ccc(n1)c(-c1ccccc1)c1ccc([nH]1)c2-c1ccccc1 IPFASKMZBDWRNG-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- QJAIOCKFIORVFU-UHFFFAOYSA-N n,n-dimethyl-4-nitroaniline Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=C1 QJAIOCKFIORVFU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BBEVMUOEYNOTTE-UHFFFAOYSA-N pentamethyl-$l^{5}-stibane Chemical group C[Sb](C)(C)(C)C BBEVMUOEYNOTTE-UHFFFAOYSA-N 0.000 description 1
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-O pyridin-1-ium-4-carbonitrile Chemical compound N#CC1=CC=[NH+]C=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-O 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102200110980 rs28931570 Human genes 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 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
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- IJJNTMLAAKKCML-UHFFFAOYSA-N tribenzyl borate Chemical compound C=1C=CC=CC=1COB(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 IJJNTMLAAKKCML-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- FQMMZTDQJFUYSA-UHFFFAOYSA-N triheptylalumane Chemical compound CCCCCCC[Al](CCCCCCC)CCCCCCC FQMMZTDQJFUYSA-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 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
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
Definitions
- the present invention relates to a method for producing ⁇ -olefin polymers.
- lubricants for automobiles and industrial machines are desired to have low fuel consumption, energy saving, and long life, and synthetic lubricants having better viscosity characteristics (high viscosity index), low temperature characteristics (low temperature fluidity), and oxidation stability than conventionally used poly- ⁇ -olefins are desired.
- Conventional poly- ⁇ -olefin synthetic lubricants include, for example, a method of polymerizing 1-decene or 1-decene and 1-dodecene using aluminum chloride or aluminum bromide as a catalyst (Patent Document 1).
- Patent Document 1 a method of polymerizing 1-decene or 1-decene and 1-dodecene using aluminum chloride or aluminum bromide as a catalyst
- Patent Document 1 a method of polymerizing 1-decene or 1-decene and 1-dodecene using aluminum chloride or aluminum bromide as a catalyst
- Patent Document 1 a method of polymerizing 1-decene or 1-decen
- Patent Document 2 discloses a method for efficiently producing ⁇ -olefin polymers and hydrogenated ⁇ -olefin polymers using a small amount of catalyst.
- An object of the present invention is to provide a process for producing an ⁇ -olefin polymer, which is capable of producing an ⁇ -olefin polymer having excellent low-temperature fluidity.
- a manufacturing method that includes a step of mixing a specific metallocene catalyst with multiple raw material monomers to obtain a catalyst mixture before the step of polymerizing ⁇ -olefins.
- a method for producing an ⁇ -olefin polymer comprising: Step 1 of mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound (A) to convert it to a cation, an organometallic compound (C), a plurality of raw material monomers (D) differing in number of carbon atoms by two or more, and a component (E) which is at least one selected from the group consisting of alcohols (E1), phenols (E2) and ether compounds (E3) to obtain a catalyst mixture; and Step 2 of polymerizing an ⁇ -olefin containing the plurality of raw material monomers (D) using the catalyst mixture.
- Step 1 A method for producing an ⁇ -olefin polymer, comprising: Step 1 of mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound (A) to convert it to a cation, an organometallic compound (C),
- ⁇ 2> The method for producing an ⁇ -olefin polymer according to the above ⁇ 1>, wherein the ionic compound (B) is a tetraphenylborate which may have a substituent, and the organometallic compound (C) is an organoaluminum compound (C1).
- ⁇ 3> The method for producing an ⁇ -olefin polymer according to the above item ⁇ 1> or ⁇ 2>, wherein the plurality of raw material monomers (D) are 1-octene (D1) and 1-dodecene (D2).
- ⁇ 4> The method for producing an ⁇ -olefin polymer according to the above ⁇ 3>, wherein the ratio [D1/D2] of 1-octene (D1) to 1-dodecene (D2) used in the step 1 is 4:6 to 6:4 in terms of molar ratio.
- ⁇ 5> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 4>, wherein in step 1, a ratio [D/A] of the total of the plurality of raw material monomers (D) to the metallocene compound (A) is 40 to 300 in terms of a molar ratio.
- ⁇ 6> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 5>, further comprising mixing a solvent in the step 1.
- ⁇ 7> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 6>, wherein in step 1, mixing is carried out at 50° C. or lower for 30 minutes or longer.
- ⁇ 8> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 7>, wherein in step 2, an ⁇ -olefin and an organoaluminum compound (C2) are mixed, and then a catalyst mixture is mixed therewith to polymerize the ⁇ -olefin.
- C2 organoaluminum compound
- ⁇ 9> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 8>, wherein in step 2, an ⁇ -olefin and an organoaluminum compound (C2) are mixed, then a catalyst mixture is mixed, and then the temperature is raised to 80° C. or higher to polymerize the ⁇ -olefin.
- ⁇ 10> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 9>, wherein a ratio of the multiple raw material monomers (D) in the ⁇ -olefin used in the step 2 is 90 to 100 mol %.
- ⁇ 11> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 3> to ⁇ 10>, wherein a ratio [D1/D2] of 1-octene (D1) to 1-dodecene (D2) used in the step 2 is 4:6 to 6:4 in terms of a molar ratio.
- ⁇ 12> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 11>, wherein the metallocene compound (A) is a doubly bridged metallocene compound.
- X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an organic group having 1 to 20 carbon atoms containing one or more atoms selected from a halogen atom, a silicon atom, an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphorus atom.
- M represents a transition metal of Groups 4 to 6 of the periodic table.
- n is an integer of 1 to 3.
- R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a halogen-containing hydrocarbon group having 1 to 20 carbon atoms.
- L represents an atom of Group 14 of the periodic table.
- ⁇ 16> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 15>, wherein the polymerization in the step 2 is carried out in a reaction vessel having a capacity of 800 L or more.
- ⁇ 17> The method for producing an ⁇ -olefin polymer according to any one of the above ⁇ 1> to ⁇ 16>, wherein the obtained ⁇ -olefin polymer has a kinematic viscosity at 40° C. of 350 to 500 cSt and a pour point of ⁇ 50° C. or lower.
- An ⁇ -olefin polymer which satisfies the following formula (1) and has a kinematic viscosity at 40° C.
- ⁇ -olefin polymer obtained by a process having the following steps 1 and 2: Step 1: a step of mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound (A) to convert it into a cation, an organometallic compound (C), a plurality of raw material monomers (D) differing in carbon number by 2 or more, and a component (E) which is at least one selected from the group consisting of alcohols (E1), phenols (E2) and ether compounds (E3) to obtain a catalyst mixture.
- Step 1 a step of mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound (A) to convert it into a cation, an organometallic compound (C), a plurality of raw material monomers (D) differing in carbon number by 2 or more, and a component (E) which is at least one selected from the group consisting of alcohols (E1)
- Step 2 a step of polymerizing an ⁇ -olefin containing the plurality of raw material monomers (D) using the catalyst mixture.
- a method for producing a lubricating oil comprising a step of mixing an ⁇ -olefin polymer obtained by the method according to any one of the above ⁇ 1> to ⁇ 17>, or the ⁇ -olefin polymer according to any one of the above ⁇ 18> to ⁇ 22>, with at least one additive selected from the group consisting of an extreme pressure agent, an oiliness agent, an antiwear agent, an antioxidant, a metal deactivator, a rust inhibitor, and an antifoaming agent.
- the present invention provides a method for producing an ⁇ -olefin polymer that can produce an ⁇ -olefin polymer with excellent low-temperature fluidity.
- the resulting ⁇ -olefin polymer has excellent low-temperature fluidity and can therefore be suitably used as a lubricant.
- the present invention provides a method for producing an ⁇ -olefin polymer, comprising: a step 1 of mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound to convert it into a cation, an organometallic compound (C), a plurality of raw material monomers (D) differing in number of carbon atoms by two or more, and a component (E) which is at least one selected from the group consisting of alcohols (E1), phenols (E2) and ether compounds (E3) to obtain a catalyst mixture; and a step 2 of polymerizing an ⁇ -olefin containing the plurality of raw material monomers (D) using the catalyst mixture.
- A metallocene compound
- B ionic compound
- C organometallic compound
- D a plurality of raw material monomers
- D a plurality of raw material monomers
- E3 which is at least one selected from the group consisting of alcohols (E1), phenol
- Step 1 is a step of obtaining a catalyst mixture by mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound to be converted into a cation, an organometallic compound (C), a plurality of raw material monomers (D) each having a carbon number differing by two or more, and a component (E) which is at least one selected from the group consisting of alcohols (E1), phenols (E2) and ether compounds (E3).
- Examples of the metallocene compound (A) include an unbridged metallocene compound, a single-bridged metallocene compound, and a double-bridged metallocene compound.
- a double-bridged metallocene compound is preferred, and a double-bridged metallocene compound represented by the following general formula (I) is more preferred.
- R a and R b each independently represent a linking group represented by the following general formula -[L(R 1 )(R 2 )] n -.
- X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an organic group having 1 to 20 carbon atoms containing one or more atoms selected from a halogen atom, a silicon atom, an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphorus atom.
- M represents a transition metal of Groups 4 to 6 of the periodic table.
- n is an integer of 1 to 3.
- R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a halogen-containing hydrocarbon group having 1 to 20 carbon atoms.
- L represents an atom of Group 14 of the periodic table.
- X1 and X2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an organic group having 1 to 20 carbon atoms containing one or more atoms selected from a halogen atom, a silicon atom, an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphorus atom.
- M represents a transition metal of Groups 4 to 6 of the periodic table, and is preferably zirconium, titanium, or hafnium.
- R a and R b are each independently a linking group represented by -[L(R 1 )(R 2 )] n -, and are preferably -C(R 1 )(R 2 )-, -Si(R 1 )(R 2 )-, -C(R 1 )(R 2 )-C(R 1 )(R 2 )- or -Si(R 1 )(R 2 )-Si(R 1 )(R 2 )-.
- n is an integer from 1 to 3.
- R1 and R2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a halogen-containing hydrocarbon group having 1 to 20 carbon atoms, preferably a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- L represents an atom of Group 14 of the periodic table, and is preferably a carbon atom or a silicon atom.
- the doubly bridged metallocene compound represented by the general formula (I) include (1,1'-ethylene)(2,2'-ethylene)biscyclopentadienyl zirconium dichloride, (1,1'-dimethylsilylene)(2,2'-dimethylsilylene)biscyclopentadienyl zirconium dichloride, (1,1'-dimethylsilylene)(2,2'-ethylene)biscyclopentadienyl zirconium dichloride, (1,1'-dimethylsilylene)(2,2'-ethylene)biscyclopentadienyl zirconium dichloride, (1,1'-isopropylidene)(2,2'- Examples of such compounds include dichlorides such as (1,1'-isopropylidene)(2,2'-isopropylidene)bis(3-methylcyclopentadienyl)zirconium dichloride, as well as dimethyl, diethyl, dihydr
- the ionic compound (B) is not limited as long as it is an ionic compound capable of reacting with the metallocene compound (A) to be converted into a cation.
- the ionic compound (B) is preferably a compound represented by the following general formula (V) or a compound represented by the following general formula (VI), and more preferably a compound represented by the following general formula (V). ([L 1 ⁇ R 3 ] k+ ) a ([Z] ⁇ ) b ... (V) ([L 2 ] k+ ) a ([Z] ⁇ ) b ... (VI)
- L1 represents a Lewis base
- R3 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a hydrocarbon group having 6 to 20 carbon atoms selected from an aryl group, an alkylaryl group, and an arylalkyl group.
- L1 include amines such as ammonia, methylamine, aniline, dimethylamine, diethylamine, N-methylaniline, diphenylamine, N,N-dimethylaniline, trimethylamine, triethylamine, tri-n-butylamine, methyldiphenylamine, pyridine, p-bromo-N,N-dimethylaniline, p-nitro-N,N-dimethylaniline, phosphines such as triethylphosphine, triphenylphosphine, diphenylphosphine, thioethers such as tetrahydrothiophene, esters such as ethyl benzoate, nitriles such as acetonitrile, benzonitrile, etc.
- R3 include a hydrogen atom, a methyl group, an ethyl group, a benzyl group, a trityl group, etc.
- L2 represents M1 , R4R5M2 , R63C or R7M2 .
- R4 and R5 each independently represent a cyclopentadienyl group, a substituted cyclopentadienyl group, an indenyl group or a fluorenyl group
- R6 represents an alkyl group having 1 to 20 carbon atoms or a hydrocarbon group having 6 to 20 carbon atoms selected from an aryl group, an alkylaryl group and an arylalkyl group.
- R7 represents a macrocyclic ligand such as tetraphenylporphyrin or phthalocyanine.
- M 1 includes an element of Groups 1 to 3 and 11 to 13 of the periodic table
- M 2 represents an element of Groups 7 to 12 of the periodic table.
- R 4 and R 5 include a cyclopentadienyl group, a methylcyclopentadienyl group, an ethylcyclopentadienyl group, and a pentamethylcyclopentadienyl group.
- R 6 include a phenyl group, a p-tolyl group, and a p-methoxyphenyl group
- R 7 include tetraphenylporphyrin and phthalocyanine.
- M 1 include Li, Na, K, Ag, and Cu
- specific examples of M 2 include Mn, Fe, Co, Ni, and Zn.
- k is the ionic valence of [L 1 -R 3 ] and [L 2 ] and is an integer of 1 to 3
- a is an integer of 1 or more
- b (k ⁇ a).
- [Z] - represents a non-coordinating anion [Z 1 ] - or [Z 2 ] - .
- [Z 1 ] - represents an anion in which a plurality of groups are bonded to an element, that is, [M 3 G 1 G 2 ... G f ] - .
- M 3 represents an element of Groups 5 to 15 of the periodic table, preferably an element of Groups 13 to 15 of the periodic table.
- G 1 to G f each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a dialkylamino group having 2 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, a halogen-substituted hydrocarbon group having 1 to 20 carbon atoms, an acyloxy group or an organic metalloid group having 1 to 20 carbon atoms, or a heteroatom-containing hydrocarbon group having 2 to 20 carbon atoms.
- G 1 to G f may form a ring.
- f represents an integer of [(the valence of the central metal M 3 ) + 1].
- [Z 2 ] ⁇ represents a conjugate base of a single Br ⁇ nsted acid or a combination of a Br ⁇ nsted acid and a Lewis acid having a logarithm of the reciprocal of the acid dissociation constant (pKa) of ⁇ 10 or less, or a conjugate base of an acid generally defined as a superacid.
- a Lewis base may be coordinated.
- M 3 include B, Al, Si, P, As, Sb, etc., and preferably B and Al.
- G 1 and G 2 to G f include dialkylamino groups such as dimethylamino and diethylamino, alkoxy groups or aryloxy groups such as methoxy, ethoxy, n-propoxy, and phenoxy, hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-octyl, n-eicosyl, phenyl, p-tolyl, benzyl, 4-t-butylphenyl, and 3,5-dimethylphenyl, halogen atoms such as fluorine, chlorine, bromine, Examples of iodine and heteroatom-containing hydrocarbon groups include
- non-coordinating anions that is, the conjugate base [Z 2 ] ⁇ of a single Bronsted acid or a combination of a Bronsted acid and a Lewis acid having a pKa of ⁇ 10 or less
- trifluoromethanesulfonate anion CF 3 SO 3 ) ⁇
- bis(trifluoromethanesulfonyl)methyl anion bis(trifluoromethanesulfonyl)benzyl anion, bis(trifluoromethanesulfonyl)amide
- perchlorate anion (ClO 4 ) ⁇ trifluoroacetate anion (CF 3 COO) ⁇ , hexafluoroantimony anion (SbF 6 ) ⁇
- fluorosulfonate anion (FSO 3 ) ⁇ chlorosulfonate anion (ClSO 3 ) ⁇
- the ionic compound (B) is preferably a tetraphenylborate salt which may have a substituent.
- Specific examples of the ionic compound (B) include triethylammonium tetraphenylborate, tri-n-butylammonium tetraphenylborate, trimethylammonium tetraphenylborate, tetraethylammonium tetraphenylborate, methyl(tri-n-butyl)ammonium tetraphenylborate, benzyl(tri-n-butyl)ammonium tetraphenylborate, dimethyldiphenylammonium tetraphenylborate, triphenyl(methyl)ammonium tetraphenylborate, trimethylanilinium tetraphenylborate, methylpyridinium tetraphenylborate, benzylpyridinium tetraphenyl
- the organometallic compound (C) is preferably at least one selected from the group consisting of organoaluminum compounds and organozinc compounds, and more preferably an organoaluminum compound (C1).
- organoaluminum compound a compound represented by the general formula (VII) is used. (R 8 ) v AlQ 3-v ...
- R8 is an alkyl group having 1 to 10 carbon atoms
- Q is a hydrogen atom, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or a halogen atom
- v is an integer of 1 to 3 or 1.5.
- organozinc compound a compound represented by the general formula (VIII) is used. (R 9 ) u ZnP 2-u ...
- R9 represents an alkyl group having 1 to 10 carbon atoms
- P represents an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or a halogen atom
- u represents an integer of 1 or 2.
- organoaluminum compounds represented by the general formula (VII) include trimethylaluminum, triethylaluminum, tri-normal propylaluminum, triisopropylaluminum, tri-normal butylaluminum, triisobutylaluminum, triheptylaluminum, trioctylaluminum, diisobutylaluminum hydride, diethylaluminum hydride, dimethylaluminum chloride, diethylaluminum chloride, methylaluminum dichloride, ethylaluminum dichloride, dimethylaluminum fluoride, and ethylaluminum sesquichloride, with triisobutylaluminum being preferred.
- organozinc compound represented by the general formula (VIII) examples include dimethylzinc, diethylzinc, dibutylzinc, dioctylzinc, and the like.
- the organometallic compound (C) may be used alone or in combination of two or more kinds.
- the molar ratio of the metallocene compound (A) to the ionic compound (B) is preferably 10:1 to 1:100, more preferably 2:1 to 1:10.
- the molar ratio of the metallocene compound (A) to the organometallic compound (C) is preferably 1:1 to 1:10,000, more preferably 1:10 to 1:1,000.
- the ionic compound (B) and the organometallic compound (C) can each be used alone or in combination of two or more kinds. When two or more kinds are used in combination, it is preferable from the viewpoint of catalytic activity that the total ratio of the two or more kinds is within the above range.
- the multiple raw material monomers (D) used in step 1 are ⁇ -olefins having different carbon numbers of 2 or more, and are included in the ⁇ -olefins polymerized in step 2.
- ⁇ -olefins with carbon numbers differing by 2 or more in this step an ⁇ -olefin polymer with excellent low-temperature fluidity can be obtained.
- the multiple raw material monomers (D) are preferably ⁇ -olefins having 3 to 30 carbon atoms, more preferably ⁇ -olefins having 6 to 20 carbon atoms, and even more preferably ⁇ -olefins having 8 to 16 carbon atoms.
- the multiple raw material monomers (D) include propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-icosene, 1-henicosene, 1-docosene, 1-tricosene, 1-tetracosene,
- Examples of the raw material monomers (D) include 1-pentacosene, 1-hexacosene, 1-heptacosene, 1-octacosene, 1-nonacosene, and 1-triacontene.
- the raw material monomers (D) are two or more of these monomers differing in carbon number by two or more.
- the raw material monomers (D) are preferably at least two monomers selected from the group consisting of 1-octene, 1-nonene, 1-decene, 1-undecene, and 1-dodecene, and more preferably 1-octene (D1) and 1-dodecene (D2).
- the ratio [D1/D2] of 1-octene (D1) to 1-dodecene (D2) used in step 1 is preferably 3:7 to 7:3, more preferably 4:6 to 6:4, and even more preferably 4.5:5.5 to 5.5:4.5 (45:55 to 55:45) in terms of molar ratio.
- the multiple raw material monomers (D) have a carbon number difference of 2 or more between the first raw material monomer and the second raw material monomer, and the difference in the carbon number between the first raw material monomer and the second raw material monomer is 2 or more, preferably 3 or more, and more preferably 4 or more.
- the difference in the carbon number between the first raw material monomer and the second raw material monomer is preferably 6 or less, more preferably 5 or less, and even more preferably 4.
- At least two kinds of raw material monomers (D) are used, but three or more kinds may be used. When three or more kinds are used, at least two of them have different carbon numbers by 2 or more.
- the number of raw material monomers (D) is preferably two.
- the raw material monomers (D) may be used as they are in the polymerization reaction, but it is more preferable to treat them with an adsorbent such as activated alumina or molecular sieve before use, since this removes impurities and improves activity.
- the ratio [D/A] of the total of the multiple raw material monomers (D) to the metallocene compound (A), in terms of molar ratio, is preferably 1 to 1000, and more preferably 40 to 300.
- the amount of the multiple raw material monomers (D) used within the above range is preferably 0.1 to 30 volume %, more preferably 0.5 to 20 volume %, even more preferably 0.5 to 15 volume %, still more preferably 0.6 to 12 volume %, and even more preferably 0.6 to 10 volume %, based on the catalyst mixture obtained in step 1.
- the amount of the multiple raw material monomers (D) used within the above range the low-temperature fluidity of the ⁇ -olefin polymer can be improved.
- the component (E) in step 1 is at least one selected from the group consisting of alcohols (E1), phenols (E2) and ether compounds (E3), and is preferably an alcohol (E1).
- component (E) particularly alcohols (E1)
- the low-temperature fluidity of the ⁇ -olefin polymer can be further improved.
- the reason for this is unclear, but is thought to be as follows. It is presumed that activated and inactivated forms coexist in the catalyst solution in step 1, and it is believed that, particularly in the catalyst solution to which alcohols (E1) have been added, the alcohols act on the activated structure to form a protective structure, thereby suppressing the generation of inactivated forms and contributing to improved catalyst activity.
- this protective structure By becoming an activated form with this protective structure, it becomes easier for multiple raw material monomers having different molecular weights to act on each other, and it becomes easier for structural units derived from multiple raw material monomers to be randomly arranged, and it is believed that the obtained polymer has excellent low-temperature fluidity.
- the alcohol (E1) is preferably an alcohol having 1 to 20 carbon atoms, more preferably an alcohol having 1 to 8 carbon atoms, and even more preferably an alcohol having 1 to 6 carbon atoms.
- Specific examples of the alcohol include methyl alcohol, ethyl alcohol, 1-propyl alcohol, 2-propyl alcohol, 1-butyl alcohol, 2-butyl alcohol, isobutyl alcohol, tertiary butyl alcohol, 1-pentyl alcohol, 2-pentyl alcohol, 3-methyl-1-butyl alcohol, 1-hexyl alcohol, cyclohexyl alcohol, 1-heptyl alcohol, 1-octyl alcohol, 2-ethylhexyl alcohol, triphenylmethanol, 1,2-ethanediol, 1,2-propanediol, benzyl alcohol, ⁇ -methylbenzyl alcohol, and the like, and is preferably tertiary butyl alcohol.
- the alcohol (E1) may be used alone or in combination of
- the phenol (E2) is preferably a phenol having 6 to 20 ring carbon atoms, more preferably a phenol having 6 to 14 ring carbon atoms, and even more preferably a phenol having 6 to 12 ring carbon atoms.
- Specific examples of the phenol include phenol, catechol, cresol, naphthol, 4-phenylphenol, thymol, and bisphenol A.
- the phenol (E2) may be used alone or in combination of two or more.
- R 10 and R 11 are each independently a hydrocarbon group having 1 to 20 carbon atoms or a halogen-containing hydrocarbon group having 1 to 20 carbon atoms, and the total number of carbon atoms of R 10 and R 11 is preferably 8 or less.
- the ether compound examples include dimethyl ether, diethyl ether, dipropyl ether, dibutyl ether, diamyl ether, dioctyl ether, didecyl ether, methyl normal butyl ether, methyl isobutyl ether, methyl tertiary butyl ether, ethyl normal butyl ether, ethyl isobutyl ether, ethyl tertiary butyl ether, methyl phenyl ether, chloromethyl methyl ether, chloromethyl ethyl ether, bromomethyl methyl ether, 2,2-dichloroethyl methyl ether, 2-chloroethyl methyl ether, 2-bromoethyl methyl ether, 2-chloroethyl ethyl ether, ⁇ , ⁇ -dichloromethyl methyl ether, 1-chloro-2,2,2-trifluoroethyl
- the ratio (usage ratio) of the metallocene compound (A) to the component (E) [A/E] is preferably 10:1 to 1:100, more preferably 1:1 to 1:50, and even more preferably 1:1 to 1:30, in terms of molar ratio.
- the ratio of the organometallic compound (C) to the component (E) is preferably less than 1, and the molar ratio of the organometallic compound (C) to the component (E) is preferably 10:9 to 1000:1.
- the alcohol (E1) which is the component (E) is generally added in large quantities as a terminator after the polymerization reaction. Surprisingly, in the present invention, activity can be improved by adding a small amount of the component (E) before polymerization.
- a solvent may be further mixed, and it is preferable to mix a solvent from the viewpoint of uniformly mixing each component of the catalyst mixture.
- the solvent that can be used in step 1 is preferably at least one selected from the group consisting of aromatic hydrocarbons, alicyclic hydrocarbons, aliphatic hydrocarbons, and halogenated hydrocarbons, and more preferably aromatic hydrocarbons.
- aromatic hydrocarbons include benzene, toluene, xylene, and ethylbenzene, and are preferably toluene or xylene, and more preferably toluene.
- alicyclic hydrocarbon examples include cyclopentane, cyclohexane, and methylcyclohexane.
- Aliphatic hydrocarbons include pentane, hexane, heptane, octane, and the like.
- halogenated hydrocarbons include chloroform and dichloromethane.
- the solvent may be used alone or in combination of two or more kinds.
- the amount of the solvent used is not particularly limited, but is preferably an amount that results in a concentration of the metallocene compound (A) of 0.1 to 10 mmol/L, more preferably an amount that results in a concentration of 0.5 to 5 mmol/L, and even more preferably an amount that results in a concentration of 1 to 3 mmol/L.
- Step 1 is the step of mixing the above components to obtain a catalyst mixture.
- mixing is preferably carried out at 50° C. or lower for 30 minutes or longer.
- the temperature when the above components are mixed is preferably 50° C. or lower, more preferably 40° C. or lower, and even more preferably 30° C. or lower.
- the lower limit is preferably 0° C. or higher, and more preferably 10° C. or higher.
- the time for mixing the above components is preferably 30 minutes or more, more preferably 30 minutes to 10 hours, and even more preferably 1 to 7 hours. That is, in step 1, mixing is preferably carried out for 30 minutes or more at 50° C. or lower.
- Step 2 is a step of polymerizing an ⁇ -olefin containing the plurality of raw material monomers (D) using the catalyst mixture.
- the production process of the present invention is for obtaining an ⁇ -olefin polymer by polymerizing an ⁇ -olefin
- the ⁇ -olefin used in step 2 is a raw material for the ⁇ -olefin polymer.
- the ⁇ -olefin used in step 2 contains the plurality of raw material monomers (D).
- the ⁇ -olefin used in step 2 is preferably an ⁇ -olefin having 3 to 30 carbon atoms, more preferably an ⁇ -olefin having 6 to 20 carbon atoms, and even more preferably an ⁇ -olefin having 8 to 14 carbon atoms.
- ⁇ -olefin examples include propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-icosene, 1-henicosene, 1-docosene, 1-tricosene, 1-tetracosene, 1-pentacosene, 1-hexacosene, 1-heptacosene, 1-octacosene, 1-nonacosene, and 1-triacontene.
- examples of the raw material monomers (D) include propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-icosene, and 1-hexene. D1) and 1-dodecene (D2).
- the ratio of 1-octene (D1) to 1-dodecene (D2) used in step 2 [D1/D2] is preferably 3:7 to 7:3, more preferably 4:6 to 6:4, and even more preferably 4.5:5.5 to 5.5:4.5 (45:55 to 55:45) in terms of molar ratio.
- the ratio of the multiple raw material monomers (D) in the ⁇ -olefin used in step 2 is preferably 70 to 100 mol %, more preferably 80 to 100 mol %, even more preferably 90 to 100 mol %, and still more preferably 95 to 100 mol %.
- the ⁇ -olefin used in step 2 may be composed only of the multiple raw material monomers (D), or may be composed only of 1-octene (D1) and 1-dodecene (D2).
- the ⁇ -olefin used in step 2 contains the plurality of raw material monomers (D) and therefore at least two types are used, but three or more types may be used, and two types are preferred.
- the ⁇ -olefin used in step 2 may be used as it is in the polymerization reaction, but it is more preferable to treat it with an adsorbent such as activated alumina or molecular sieve before use, since this removes impurities and improves activity.
- the amount of ⁇ -olefin used as the raw material is preferably 200 kg or more, more preferably 300 kg or more, even more preferably 400 kg or more, and even more preferably 500 kg or more.
- the polymerization method is not particularly limited, and any method such as bulk polymerization, solution polymerization, suspension polymerization, slurry polymerization, and gas phase polymerization may be used.
- the polymerization temperature is preferably 0 to 200°C, more preferably 30 to 150°C, even more preferably 40 to 120°C, and still more preferably 80 to 120°C.
- the ratio of the catalyst to the raw material ⁇ -olefin that is, the molar ratio of the ⁇ -olefin used in step 2 to the metallocene compound (A) used in step 1 [ ⁇ -olefin/metallocene compound (A)] is preferably 1 to 10 8 , more preferably 100 to 10 6 .
- the polymerization time is preferably 5 minutes to 20 hours, and the reaction pressure is preferably 0 to 0.2 MPaG, where "MPaG" represents "MPa (gauge pressure)."
- the polymerization is preferably performed without a solvent, but a solvent may be used.
- the solvent that can be used in step 2 is preferably at least one selected from the group consisting of aromatic hydrocarbons, alicyclic hydrocarbons, aliphatic hydrocarbons, and halogenated hydrocarbons, and more preferably aromatic hydrocarbons.
- aromatic hydrocarbons include benzene, toluene, xylene, and ethylbenzene, and toluene or xylene is preferable, and toluene is more preferable.
- the alicyclic hydrocarbon include cyclopentane, cyclohexane, and methylcyclohexane.
- Aliphatic hydrocarbons include pentane, hexane, heptane, octane, and the like.
- halogenated hydrocarbons include chloroform and dichloromethane.
- the solvent may be used alone or in combination of two or more kinds.
- step 2 when polymerizing ⁇ -olefins, it is preferable to add hydrogen because the activity is improved by adding hydrogen.
- the hydrogen partial pressure is preferably 0.2 MPaG or less, and more preferably 0.1 MPaG or less.
- the lower limit of the hydrogen partial pressure is 0.01 MPaG.
- Step 2 is a step of polymerizing an ⁇ -olefin using the catalyst mixture, and in step 2, it is preferable to mix the ⁇ -olefin with an organoaluminum compound (C2), and then mix the catalyst mixture to polymerize the ⁇ -olefin.
- the organoaluminum compound (C2) used here is the same as the organoaluminum compound (C1) used in step 1, and the preferred compounds are also the same. It is more preferable that the organoaluminum compound (C2) and the organoaluminum compound (C1) are the same compound.
- step 2 it is more preferable to mix the ⁇ -olefin with the organoaluminum compound (C2), then mix the catalyst mixture, and then raise the temperature to 80° C. or higher to polymerize the ⁇ -olefin.
- the preferred polymerization temperature is as described above, and is preferably 80 to 120° C.
- the molecular weight of the ⁇ -olefin polymer can be adjusted by adjusting the type, amount of each catalyst component used, reaction amount, polymerization temperature, and solvent.
- the polymerization in step 2 is preferably carried out in a reaction vessel having a capacity of 700 L or more, more preferably in a reaction vessel having a capacity of 800 L or more, and even more preferably in a reaction vessel having a capacity of 1000 L or more. It is believed that by increasing the reaction scale, the effect of the reactor wall on the catalytic activity is reduced, and the obtained ⁇ -olefin polymer has better low-temperature fluidity.
- Methods for removing the monomer and oligomer components include, for example, distillation.
- the ⁇ -olefin polymer obtained in step 2 may be used as it is as a lubricant, a lubricant base oil, or an additive for a lubricant, but it is preferable to further hydrogenate it.
- the ⁇ -olefin polymer obtained by the production method of the present invention includes hydrogenated ⁇ -olefin polymers, and the ⁇ -olefin polymer of the present invention described below also includes hydrogenated ⁇ -olefin polymers. Hydrogenation can improve stability.
- the reaction conditions for the hydrogenation step may be general hydrogenation reaction conditions, but the preferred conditions are as follows. In this hydrogenation step, a commonly used gas phase hydrogenation method can be used.
- the reaction temperature is preferably 60 to 100°C and the hydrogen pressure is preferably 0.1 to 1 MPa.
- the reaction temperature is preferably 100 to 250°C and the hydrogen pressure is preferably 0.1 to 20 MPa.
- the amount of catalyst is preferably 0.05 to 50 mass% relative to the polymer obtained in step 2, and the reaction time is preferably 2 to 48 hours.
- the hydrogenation reaction proceeds quickly by using the hydrogenation catalyst, but additional operations such as temperature increase or pressure increase may be performed even after significant absorption of hydrogen has ceased in order to completely hydrogenate the remaining trace amounts of raw material.
- the ⁇ -olefin polymer obtained by the above production method has excellent low-temperature fluidity. That is, the present invention also includes an ⁇ -olefin polymer obtained by a method including a step 1 of mixing a metallocene compound (A), an ionic compound (B) capable of reacting with the metallocene compound (A) to convert to a cation, an organometallic compound (C), a plurality of raw material monomers (D) differing in carbon number by 2 or more, and a component (E) which is at least one selected from the group consisting of alcohols (E1), phenols (E2) and ether compounds (E3) to obtain a catalyst mixture, and a step 2 of polymerizing an ⁇ -olefin containing the plurality of raw material monomers (D) using the catalyst mixture.
- the plurality of raw material monomers (D) are preferably 1-octene (D1) and 1-dodecene (D2).
- the present invention also includes an ⁇ -olefin polymer that satisfies the following formula (1) and has a kinematic viscosity at 40° C. of 350 cSt or more and 1500 cSt or less. (Pour point (°C)) ⁇ 0.0090 ⁇ (40°C kinematic viscosity (cSt)) ⁇ 52 (1)
- the ⁇ -olefin polymer obtained by the above production method is preferably an ⁇ -olefin polymer which satisfies the above formula (1) and has a 40° C. kinetic viscosity of 350 cSt or more and 1500 cSt or less, and more preferably satisfies the following formula (3), and even more preferably satisfies the following formula (4).
- An ⁇ -olefin polymer having a 40° C. kinematic viscosity of 350 cSt or more and 1500 cSt or less and satisfying the above formulae has excellent low-temperature fluidity.
- the kinetic viscosity is measured in accordance with JIS K 2283.
- the ⁇ -olefin polymer preferably has a kinematic viscosity at 40° C. of 350 to 500 cSt and a pour point of ⁇ 50° C. or lower.
- the above-mentioned ⁇ -olefin polymer is preferably an ⁇ -olefin polymer satisfying the following formula (2): (Pour point (°C)) ⁇ 0.3 ⁇ (viscosity index) ⁇ 103 (2)
- the ⁇ -olefin polymer satisfying the formula (2) is preferably an ⁇ -olefin polymer satisfying the following formula (5), and more preferably an ⁇ -olefin polymer satisfying the following formula (6).
- the ⁇ -olefin polymer obtained by the production method is preferably an ⁇ -olefin polymer satisfying the formula (2), and more preferably an ⁇ -olefin polymer satisfying the following formula (5), and even more preferably an ⁇ -olefin polymer satisfying the following formula (6).
- the viscosity index (VI) of the ⁇ -olefin polymer is preferably not more than 220, more preferably not more than 200, and even more preferably not more than 180.
- the lower limit is preferably 100 or more.
- the viscosity index is determined by calculation in accordance with JIS K 2283 from the kinematic viscosity measured in accordance with JIS K 2283.
- the obtained ⁇ -olefin polymer preferably satisfies the above-mentioned requirements. Specific examples are shown below.
- the obtained ⁇ -olefin polymer preferably satisfies the following formula (1) and has a kinematic viscosity at 40° C. of 350 cSt or more and 1500 cSt or less. (Pour point (°C)) ⁇ 0.0090 ⁇ (40°C kinematic viscosity (cSt)) ⁇ 52 (1)
- kinematic viscosity of 350 cSt or more and 1500 cSt or less preferably satisfies the following formula (3), and more preferably satisfies the following formula (4).
- An ⁇ -olefin polymer having a 40° C. kinematic viscosity of 350 cSt or more and 1500 cSt or less and satisfying the above formulae has excellent low-temperature fluidity.
- the kinematic viscosity is measured in accordance with JIS K 2283.
- the ⁇ -olefin polymer obtained preferably has a 40° C. kinematic viscosity of 350 to 500 cSt and a pour point of ⁇ 50° C. or lower.
- the obtained ⁇ -olefin polymer preferably satisfies the following formula (2): (Pour point (°C)) ⁇ 0.3 ⁇ (viscosity index) ⁇ 103 (2)
- the ⁇ -olefin polymer satisfying formula (2) obtained by the method for producing an ⁇ -olefin polymer of the present invention is preferably an ⁇ -olefin polymer satisfying the following formula (5), and more preferably an ⁇ -olefin polymer satisfying the following formula (6): (Pour point (°C)) ⁇ 0.3 ⁇ (Viscosity index) ⁇ 104 (5) (Pour point (°C)) ⁇ 0.3 ⁇ (Viscosity index) ⁇ 105 (6)
- the viscosity index (VI) of the ⁇ -olefin polymer is preferably not more than 220, more preferably not more than 200, and even more preferably not more than 180. The lower limit is preferably 100 or more.
- the viscosity index is determined by
- the ⁇ -olefin polymer preferably contains a structural unit derived from 1-octene and a structural unit derived from 1-dodecene.
- the total ratio of the constituent units derived from 1-octene and the constituent units derived from 1-dodecene in the ⁇ -olefin polymer is preferably 90 to 100 mol %.
- the molar ratio of the constituent units derived from 1-octene to the constituent units derived from 1-dodecene in the ⁇ -olefin polymer is preferably 3:7 to 7:3, more preferably 4:6 to 6:4, and even more preferably 4.5:5.5 to 5.5:4.5 (45:55 to 55:45).
- the present invention also includes lubricating oils containing the above-mentioned ⁇ -olefin polymers, and lubricating oils containing the ⁇ -olefin polymers obtained by the above-mentioned production method.
- additives can be used in the lubricating oil of the present invention as long as the effects of the present invention are not impaired.
- additives include extreme pressure agents, oiliness agents, antiwear agents, antioxidants, metal deactivators, rust inhibitors and antifoam agents.
- the method for producing the lubricating oil is preferably a method for producing a lubricating oil that includes a step of mixing the ⁇ -olefin polymer obtained by the method described above or the ⁇ -olefin polymer with at least one additive selected from the group consisting of extreme pressure agents, oiliness agents, antiwear agents, antioxidants, metal deactivators, rust inhibitors, and antifoaming agents.
- the extreme pressure agent examples include sulfur-based extreme pressure agents, phosphorus-based extreme pressure agents, extreme pressure agents containing sulfur and metal, and extreme pressure agents containing phosphorus and metal. These extreme pressure agents can be used alone or in combination of two or more.
- the extreme pressure agent may be any agent that contains sulfur atoms and/or phosphorus atoms in the molecule and can exhibit load resistance and wear resistance.
- the amount of the extreme pressure agent blended is usually about 0.01 to 30 mass %, and preferably 0.01 to 10 mass %, based on the total amount of the lubricating oil, from the standpoint of blending effect and economy.
- oily agents examples include fatty alcohols, fatty acids and fatty acid metal salts and other fatty acid compounds, polyol esters, sorbitan esters, glycerides and other ester compounds, and fatty amines and other amine compounds.
- the amount of the oiliness agent to be added is usually about 0.1 to 30 mass %, and preferably 0.5 to 10 mass %, based on the total amount of the lubricating oil, from the viewpoint of the effect of the addition.
- anti-wear agents include sulfur-containing compounds such as zinc dialkyldithiophosphate (ZnDTP), zinc phosphate, disulfides, sulfurized olefins, sulfurized oils and fats, sulfurized esters, thiocarbonates, thiocarbamates, and polysulfides; phosphorus-containing compounds such as phosphites, phosphates, phosphonates, and amine salts or metal salts thereof; and sulfur- and phosphorus-containing anti-wear agents such as thiophosphites, thiophosphates, thiophosphonates, and amine salts or metal salts thereof.
- the amount of the anti-wear agent blended is usually about 0.01 to 30 mass %, and more preferably 0.01 to 10 mass %, based on the total amount of the lubricating oil, from the viewpoints of blending effect and economy.
- the antioxidant is preferably at least one selected from the group consisting of phenol-based antioxidants, amine-based antioxidants, and zinc dialkyldithiophosphates, more preferably at least one selected from the group consisting of phenol-based antioxidants and amine-based antioxidants, and even more preferably a phenol-based antioxidant.
- phenol-based antioxidants tetrakis[methylene-3-(3',5-di-t-butyl-4'-hydroxyphenyl)propionate]methane is preferred.
- a plurality of these antioxidants may be used in combination, or one of these antioxidants may be used in combination with an antioxidant having a peroxide decomposition function.
- Antioxidants having a peroxide decomposition function include organic sulfur-based antioxidants, and zinc dialkyldithiophosphate has both a radical scavenging function and a peroxide decomposition function.
- the amount of the antioxidant contained in the lubricating oil of the present invention is preferably 0.1 mass% or more, more preferably 0.2 mass% or more, even more preferably 0.3 mass% or more, and even more preferably 0.4 mass% or more, based on the total amount of the lubricating oil. It is preferably 10 mass% or less, and may be 5 mass% or less, or may be 3 mass% or less.
- metal deactivators examples include benzotriazole and thiadiazole. From the viewpoint of the compounding effect, the preferred compounding amount of the metal deactivator is usually about 0.01 to 10 mass% based on the total amount of the lubricating oil, and preferably 0.01 to 1 mass%.
- rust inhibitors examples include metal sulfonates and succinic acid esters. From the viewpoint of compounding effectiveness, the amount of rust inhibitor to be added is usually about 0.01 to 10 mass% based on the total amount of lubricating oil, and preferably 0.05 to 5 mass%.
- defoamers examples include methylsilicone oil, fluorosilicone oil, polyacrylate, etc. From the viewpoint of compounding effect, the amount of defoamer to be added is usually about 0.0005 to 0.01 mass% based on the total amount of lubricating oil.
- the content of the ⁇ -olefin polymer of the present invention in the lubricating oil is preferably 55% by mass or more, more preferably 60% by mass or more, and even more preferably 80% by mass or more. It may also be 100% by mass or less, and may consist of only the ⁇ -olefin polymer of the present invention. When it is within the above range, the effects of the present invention are fully exerted, and low fuel consumption, energy saving, and long life can be achieved.
- Example 1 A 30 L stainless steel vessel was charged with 18.9 kg of toluene that had been dehydrated to a water content of 10 ppm or less under a nitrogen atmosphere, 0.89 kg of triisobutylaluminum (C1) (20% toluene solution), 0.0198 kg of tertiary butyl alcohol (E1), 30 mmol of (1,1'-dimethylsilylene)(2,2'-dimethylsilylene)-bis(cyclopentadienyl)zirconium dichloride (A), 36 mmol of N,N-dimethylanilinium tetrakis(pentafluorophenyl)borate (B), 0.08 kg of 1-octene (D1), and 0.12 kg of 1-dodecene (D2), and the mixture was stirred at room temperature (25°C) for 2 hours to obtain a catalyst mixture.
- C1 triisobutylaluminum
- E1 tertiary butyl alcohol
- Step 2 A stainless steel reaction vessel with an internal volume of 1.2 m 3 (1200 L) was thoroughly dried and purged with nitrogen, after which 345 kg of 1-dodecene (D2) and 230 kg of 1-octene (D1) were introduced, followed by 0.19 kg of triisobutylaluminum (C2) (20% toluene solution), and the temperature was raised to 95° C. Hydrogen at 0.2 MPaG was introduced, and the catalyst mixture obtained in step 1 was continuously introduced at a rate of 0.4 kg per hour. After the start of introduction of the catalyst mixture, the internal temperature was maintained at 103° C. to carry out the reaction.
- D2 1-dodecene
- D1 1-octene
- C2 triisobutylaluminum
- reaction liquid A small amount of the reaction liquid was withdrawn during the reaction, and the conversion was measured, and the reaction was stopped when the conversion reached 90%. Distillation was carried out under reduced pressure of 50 Pa and 250° C. to remove residual monomers, etc., to obtain an ⁇ -olefin polymer.
- Example 2 A catalyst mixture was obtained in the same manner as in Example 1, except that in step 1 of Example 1, the amount of triisobutylaluminum (20% toluene solution) was changed to 1.2 kg, the amount of tert-butyl alcohol was changed to 0.0440 kg, the amount of 1-octene was changed to 0.586 kg, and the amount of 1-dodecene was changed to 0.880 kg. Using the obtained catalyst mixture, step 2 and the hydrogenation step were performed in the same manner as in Example 1, to obtain an ⁇ -olefin polymer.
- Comparative Example 1 (Step 1) In a 500 mL glass Schlenk flask, 334 mL of special grade toluene that had been dehydrated to 10 ppm or less of water was added under a nitrogen atmosphere, 40 mL of 1-octene, 24 mmol of triisobutylaluminum (2 mmol/mL toluene solution; 12 mL), and 14.4 mmol of tertiary butyl alcohol were added and stirred at room temperature for 1 hour.
- Step 2 A stainless steel autoclave with an internal volume of 30 L was thoroughly dried and purged with nitrogen, after which 8.0 kg (10.5 L) and 5.4 kg (7.5 L) of 1-dodecene and 1-octene were introduced, respectively, followed by 5.4 mmol of triisobutylaluminum, and the temperature was raised to 95°C. Hydrogen was introduced at 0.02 MPaG, and the catalyst mixture obtained in step 1 was continuously introduced at a rate of 36 mL per hour using a plunger pump. After the start of catalyst introduction, the internal temperature was maintained at 102°C and the reaction was carried out for 5 hours. A small amount of the reaction liquid was withdrawn during the reaction, and the conversion rate was measured.
- a thin-film distillation apparatus (special model molecular distillation apparatus MS-300, high vacuum exhaust apparatus DS-212Z, manufactured by Shibata Scientific Co., Ltd.) to remove low molecular weight components having a carbon number of 24 or less, to obtain an ⁇ -olefin polymer.
- ⁇ -olefin polymer obtained in step 2 was placed in a stainless steel autoclave with an internal volume of 1 liter, and 1% by mass of a stabilized nickel catalyst (SN750 manufactured by Sakai Chemical Industry Co., Ltd.) was added thereto, followed by reaction for 6 hours at 130° C. under hydrogen of 2 MPa. After completion of the reaction, the temperature was cooled to about 80° C., and the contents were then removed, and the catalyst component was filtered and separated at about 70° C. using a 2 ⁇ m filter, to obtain a colorless and transparent hydrogenated ⁇ -olefin polymer.
- SN750 manufactured by Sakai Chemical Industry Co., Ltd.
- the ⁇ -olefin polymers obtained in the examples have a very low pour point and excellent low-temperature fluidity compared to the ⁇ -olefin polymers of the comparative examples, despite having a similar 40°C kinetic viscosity. This shows that the ⁇ -olefin polymers of the present invention also have excellent performance when used as lubricants. By using the ⁇ -olefin polymers of the present invention as lubricants, it is possible to achieve lower fuel consumption, energy savings, and longer life.
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Abstract
La présente invention concerne un procédé de production d'un polymère d'α-oléfine, le procédé comprenant : une étape 1 d'obtention d'un mélange de catalyseur par mélange d'un composé métallocène (A), d'un composé ionique (B) qui peut être converti en cations par réaction avec le composé métallocène (A), d'un composé organométallique (C), d'une pluralité de monomères de matière première (D) dont au moins deux ont des nombres d'atomes de carbone différents, et d'un composant (E) qui est au moins l'un choisi dans le groupe constitué par les alcools (E1), les phénols (E2) et les composés d'éther (E3) ; et une étape 2 de polymérisation d'une α-oléfine contenant la pluralité de monomères de matière première (D) à l'aide du mélange de catalyseur.
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JP2003082018A (ja) * | 2001-06-29 | 2003-03-19 | Japan Polychem Corp | オレフィンの重合方法 |
WO2011093295A1 (fr) * | 2010-01-26 | 2011-08-04 | 出光興産株式会社 | (CO)POLYMÈRE D'α-OLÉFINE, (CO)POLYMÈRE D'α-OLÉFINE HYDROGÉNÉ ET COMPOSITION D'HUILE LUBRIFIANTE LES CONTENANT |
WO2014142206A1 (fr) * | 2013-03-14 | 2014-09-18 | 出光興産株式会社 | PROCÉDÉS DE PRODUCTION D'UN POLYMÈRE α-OLÉFINIQUE ET POLYMÈRE α-OLÉFINIQUE HYDROGÉNÉ |
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JP2003082018A (ja) * | 2001-06-29 | 2003-03-19 | Japan Polychem Corp | オレフィンの重合方法 |
WO2011093295A1 (fr) * | 2010-01-26 | 2011-08-04 | 出光興産株式会社 | (CO)POLYMÈRE D'α-OLÉFINE, (CO)POLYMÈRE D'α-OLÉFINE HYDROGÉNÉ ET COMPOSITION D'HUILE LUBRIFIANTE LES CONTENANT |
WO2014142206A1 (fr) * | 2013-03-14 | 2014-09-18 | 出光興産株式会社 | PROCÉDÉS DE PRODUCTION D'UN POLYMÈRE α-OLÉFINIQUE ET POLYMÈRE α-OLÉFINIQUE HYDROGÉNÉ |
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