JP2014520078A5 - - Google Patents
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- JP2014520078A5 JP2014520078A5 JP2014510649A JP2014510649A JP2014520078A5 JP 2014520078 A5 JP2014520078 A5 JP 2014520078A5 JP 2014510649 A JP2014510649 A JP 2014510649A JP 2014510649 A JP2014510649 A JP 2014510649A JP 2014520078 A5 JP2014520078 A5 JP 2014520078A5
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- JP
- Japan
- Prior art keywords
- group
- oily
- complex
- mol
- compound
- 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.)
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- -1 acenaphthyl group Chemical group 0.000 claims description 155
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 99
- 239000003054 catalyst Substances 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 238000006116 polymerization reaction Methods 0.000 claims description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 56
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 56
- 229910052794 bromium Inorganic materials 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 55
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 54
- 150000001336 alkenes Chemical class 0.000 claims description 43
- 239000010687 lubricating oil Substances 0.000 claims description 43
- 239000002199 base oil Substances 0.000 claims description 40
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 229920000098 polyolefin Polymers 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 27
- 239000003921 oil Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 239000012442 inert solvent Substances 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 229910052759 nickel Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 230000000996 additive effect Effects 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 239000002685 polymerization catalyst Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 5
- 239000002518 antifoaming agent Substances 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000000994 depressogenic effect Effects 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 101150003085 Pdcl gene Proteins 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002816 nickel compounds Chemical class 0.000 claims description 2
- 150000002941 palladium compounds Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000000314 lubricant Substances 0.000 claims 2
- 125000005594 diketone group Chemical group 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 description 116
- 229920000573 polyethylene Polymers 0.000 description 109
- 239000003446 ligand Substances 0.000 description 70
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 64
- 239000005977 Ethylene Substances 0.000 description 64
- 239000000047 product Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 230000015572 biosynthetic process Effects 0.000 description 51
- 238000003786 synthesis reaction Methods 0.000 description 50
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 49
- 238000005481 NMR spectroscopy Methods 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- 229920000642 polymer Polymers 0.000 description 39
- 230000003197 catalytic effect Effects 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000005984 hydrogenation reaction Methods 0.000 description 26
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 16
- 229910001873 dinitrogen Inorganic materials 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 14
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 14
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 11
- 238000001308 synthesis method Methods 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 150000005826 halohydrocarbons Chemical class 0.000 description 9
- 239000004711 α-olefin Substances 0.000 description 9
- 125000005234 alkyl aluminium group Chemical group 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 238000010561 standard procedure Methods 0.000 description 7
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 6
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229920001083 polybutene Polymers 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000011630 iodine Chemical group 0.000 description 5
- 229910052740 iodine Chemical group 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 229910000071 diazene Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002356 laser light scattering Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- ZLQBNKOPBDZKDP-UHFFFAOYSA-L nickel(2+);diperchlorate Chemical compound [Ni+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O ZLQBNKOPBDZKDP-UHFFFAOYSA-L 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- XIRRDAWDNHRRLB-UHFFFAOYSA-N 2,6-dibromoaniline Chemical compound NC1=C(Br)C=CC=C1Br XIRRDAWDNHRRLB-UHFFFAOYSA-N 0.000 description 3
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- ILHIHKRJJMKBEE-UHFFFAOYSA-N hydroperoxyethane Chemical compound CCOO ILHIHKRJJMKBEE-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- KVRSDIJOUNNFMZ-UHFFFAOYSA-L nickel(2+);trifluoromethanesulfonate Chemical compound [Ni+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F KVRSDIJOUNNFMZ-UHFFFAOYSA-L 0.000 description 2
- 150000002940 palladium Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- ZYBKXMTWWFTYKN-UHFFFAOYSA-N 2,4-dibromo-6-(trifluoromethyl)aniline Chemical compound NC1=C(Br)C=C(Br)C=C1C(F)(F)F ZYBKXMTWWFTYKN-UHFFFAOYSA-N 0.000 description 1
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| CN105503763B (zh) | 2014-10-17 | 2020-11-03 | 上海中科康润新材料科技有限公司 | 聚烯烃油催化剂及其应用 |
| CN106397264B (zh) * | 2015-07-31 | 2018-07-20 | 中国石油化工股份有限公司 | 一种二亚胺配体化合物、配合物及应用 |
| CN106397263B (zh) * | 2015-07-31 | 2018-07-20 | 中国石油化工股份有限公司 | 配体化合物、其制备及含所述配体化合物的配合物 |
| CN106397261B (zh) * | 2015-07-31 | 2018-07-20 | 中国石油化工股份有限公司 | 一种二亚胺配体化合物、配合物及应用 |
| CN106397262B (zh) * | 2015-07-31 | 2018-06-12 | 中国石油化工股份有限公司 | 二亚胺配体、其制备方法及应用 |
| US9951158B2 (en) | 2016-08-12 | 2018-04-24 | Chevron Phillips Chemical Company Lp | Process for reducing the light oligomer content of polypropylene oils |
| US20180105478A1 (en) * | 2016-10-19 | 2018-04-19 | Chevron Phillips Chemical Company Lp | Process for Reducing the Light Oligomer Content of Polypropylene Oils |
| CN108864344B (zh) * | 2017-05-12 | 2020-12-18 | 中国石油化工股份有限公司 | 一种用于烯烃聚合的催化剂组合物及烯烃聚合的方法 |
| WO2019157002A1 (en) | 2018-02-06 | 2019-08-15 | Northwestern University | Highly branched, low molecular weight polyolefins and methods for their production |
| SG11202102213VA (en) | 2018-12-07 | 2021-06-29 | Exxonmobil Res & Eng Co | Processes for polymerizing internal olefins and compositions thereof |
| WO2020205708A1 (en) * | 2019-04-01 | 2020-10-08 | Exxonmobil Research And Engineering Company | Processes for polymerizing alpha-olefins, internal olefins and compositions thereof |
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| CN112725018B (zh) * | 2019-10-28 | 2023-10-20 | 南京中科康润新材料科技有限公司 | 一种低碳烯烃经聚合直接合成高性能中等粘度基础油的工艺方法 |
| CN112725017B (zh) * | 2019-10-28 | 2023-10-20 | 南京中科康润新材料科技有限公司 | 一种低碳烯烃经聚合直接合成高性能高粘度基础油的工艺方法 |
| EP4267707A1 (en) | 2020-12-23 | 2023-11-01 | The Lubrizol Corporation | Benzazepine compounds as antioxidants for lubricant compositions |
| CN115260365B (zh) * | 2021-04-29 | 2023-07-21 | 中国石油化工股份有限公司 | 支化烯烃聚合物及其制备方法和应用 |
| CN114316093B (zh) * | 2022-01-04 | 2023-04-28 | 吉林大学 | 一种苊醌双亚胺基稀土金属催化剂的制备方法及应用 |
| CN116239494B (zh) * | 2023-01-14 | 2025-12-30 | 浙江巨化技术中心有限公司 | 配体化合物及制备方法、催化剂组合物及应用、催化剂和聚乙烯弹性体及制备方法和应用 |
| WO2025184033A1 (en) | 2024-02-29 | 2025-09-04 | ExxonMobil Technology and Engineering Company | Circulating oils with improved oil life and energy efficiency |
| WO2025184041A1 (en) | 2024-02-29 | 2025-09-04 | ExxonMobil Technology and Engineering Company | Hydraulic oils with improved oil life and energy efficiency |
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| TWI258137B (en) * | 2003-04-10 | 2006-07-11 | Via Optical Solution Inc | Method and related optical disk accessing apparatus for calibrating optical disk tilt servo system according to non-constant relation between locations and tilt angles of optical disk |
| US20050077208A1 (en) * | 2003-10-14 | 2005-04-14 | Miller Stephen J. | Lubricant base oils with optimized branching |
| CN1246348C (zh) | 2004-03-12 | 2006-03-22 | 中山大学 | 合成支化聚乙烯的钛－取代苊二亚胺镍复合催化剂及其制备方法 |
| CN1942433A (zh) | 2004-04-27 | 2007-04-04 | 北卡罗来纳查佩尔山大学 | 通过液相色谱法分离不对称二亚胺 |
| CA2595946C (en) * | 2005-02-02 | 2011-03-15 | Exxonmobil Chemical Patents Inc. | Modified polyethylene compositions |
| US8748361B2 (en) | 2005-07-19 | 2014-06-10 | Exxonmobil Chemical Patents Inc. | Polyalpha-olefin compositions and processes to produce the same |
| JP5137314B2 (ja) | 2006-03-31 | 2013-02-06 | Ｊｘ日鉱日石エネルギー株式会社 | 潤滑油基油 |
| CN100500708C (zh) * | 2006-06-06 | 2009-06-17 | 中山大学 | 乙烯原位聚合的苊二亚胺镍/Fe3O4负载磁性纳米催化剂及其制备方法 |
| JP2009227996A (ja) | 2008-02-29 | 2009-10-08 | Tokyo Institute Of Technology | ジエン重合体およびその製造方法 |
| JP5551861B2 (ja) | 2008-10-07 | 2014-07-16 | Ｊｘ日鉱日石エネルギー株式会社 | 内燃機関用潤滑油組成物 |
| CN101531725B (zh) * | 2009-04-08 | 2012-12-26 | 中山大学 | α-二亚胺镍配合物烯烃聚合催化剂及其制备方法与制备支化聚乙烯的方法 |
| DE102009017827A1 (de) | 2009-04-20 | 2010-10-21 | Sasol Germany Gmbh | Verfahren zur Herstellung von verzweigten Kohlenwasserstoffen aus Fettalkoholen und Verwendung derartig hergestellter Kohlenwasserstoffe |
| CN102093425A (zh) | 2010-12-04 | 2011-06-15 | 西北师范大学 | 含有tert-butyl的α-二亚胺镍（Ⅱ）配合物及其制备 |
| CN102050840B (zh) * | 2010-12-04 | 2013-06-05 | 西北师范大学 | 含萘环的α-二亚胺镍(Ⅱ)配合物及其制备和应用 |
| CN102180910B (zh) | 2011-03-11 | 2014-03-12 | 中国科学院化学研究所 | 不对称α二亚胺镍配合物催化剂及其制备方法与应用 |
| ES2797651T3 (es) * | 2011-05-16 | 2020-12-03 | Shanghai Chemrun Co Ltd | Sistema catalítico para la preparación de alcano altamente ramificado a partir de olefinas |
| CN102250152B (zh) * | 2011-05-26 | 2014-04-16 | 中山大学 | 胺基亚胺镍乙烯聚合催化剂的制备方法和应用 |
-
2012
- 2012-04-23 ES ES12785810T patent/ES2797651T3/es active Active
- 2012-04-23 EP EP12785810.8A patent/EP2711356B1/en active Active
- 2012-04-23 WO PCT/CN2012/074545 patent/WO2012155764A1/zh not_active Ceased
- 2012-04-23 US US14/118,172 patent/US9315755B2/en active Active
- 2012-04-23 JP JP2014510649A patent/JP6175052B2/ja active Active
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2016
- 2016-03-23 US US15/078,830 patent/US10294440B2/en active Active
- 2016-05-06 JP JP2016093507A patent/JP6215391B2/ja active Active
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