JP2015506393A - 超分岐オレフィン油性誘電性流体 - Google Patents
超分岐オレフィン油性誘電性流体 Download PDFInfo
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- JP2015506393A JP2015506393A JP2014550300A JP2014550300A JP2015506393A JP 2015506393 A JP2015506393 A JP 2015506393A JP 2014550300 A JP2014550300 A JP 2014550300A JP 2014550300 A JP2014550300 A JP 2014550300A JP 2015506393 A JP2015506393 A JP 2015506393A
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- Prior art keywords
- independently
- hydrocarbyl
- unsubstituted
- atom
- olefin
- Prior art date
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- Granted
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- 239000012530 fluid Substances 0.000 title claims description 29
- 150000001336 alkenes Chemical class 0.000 title description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 13
- 239000003446 ligand Substances 0.000 claims abstract description 102
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 239000004711 α-olefin Substances 0.000 claims abstract description 40
- 229920013639 polyalphaolefin Polymers 0.000 claims abstract description 9
- -1 SR C Inorganic materials 0.000 claims description 155
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 239000005977 Ethylene Substances 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000129 anionic group Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 230000007935 neutral effect Effects 0.000 claims description 17
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 16
- 230000003197 catalytic effect Effects 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 238000009826 distribution Methods 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052735 hafnium Chemical group 0.000 claims description 5
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 239000012018 catalyst precursor Substances 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 230000009645 skeletal growth Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 27
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229930195733 hydrocarbon Natural products 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003636 chemical group Chemical group 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 229920000098 polyolefin Polymers 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000002015 acyclic group Chemical group 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000012267 brine Substances 0.000 description 8
- 125000002993 cycloalkylene group Chemical group 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 238000009413 insulation Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 150000007527 lewis bases Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- LZIPBJBQQPZLOR-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyloxyethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOS(=O)(=O)C1=CC=C(C)C=C1 LZIPBJBQQPZLOR-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- HWQXVVPRGQSQLD-UHFFFAOYSA-N 4-fluoro-1-[2-(4-fluoro-2-iodophenoxy)ethoxy]-2-iodobenzene Chemical compound IC1=CC(F)=CC=C1OCCOC1=CC=C(F)C=C1I HWQXVVPRGQSQLD-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- WBVMKBLHVKRIGY-UHFFFAOYSA-N 5-fluoro-2-[2-(4-fluoro-2-iodo-6-methylphenoxy)ethoxy]-1-iodo-3-methylbenzene Chemical compound CC1=CC(F)=CC(I)=C1OCCOC1=C(C)C=C(F)C=C1I WBVMKBLHVKRIGY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- QKLSMLAKJAUCDI-UHFFFAOYSA-N C(COC=1C(=C(C(=CC=1C(C)(CC(C)(C)C)C)C1=CC(=CC(=C1)F)C)O)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)C(C)(C)C)C(C)(C)C)OC=1C(=C(C(=CC=1C(C)(CC(C)(C)C)C)C1=CC(=CC(=C1)F)C)O)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)C(C)(C)C)C(C)(C)C Chemical compound C(COC=1C(=C(C(=CC=1C(C)(CC(C)(C)C)C)C1=CC(=CC(=C1)F)C)O)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)C(C)(C)C)C(C)(C)C)OC=1C(=C(C(=CC=1C(C)(CC(C)(C)C)C)C1=CC(=CC(=C1)F)C)O)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)C(C)(C)C)C(C)(C)C QKLSMLAKJAUCDI-UHFFFAOYSA-N 0.000 description 2
- DVZWQGLVEOWFOU-UHFFFAOYSA-N C[Hf]C Chemical compound C[Hf]C DVZWQGLVEOWFOU-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 229910007926 ZrCl Inorganic materials 0.000 description 2
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 2
- JXBAVRIYDKLCOE-UHFFFAOYSA-N [C].[P] Chemical group [C].[P] JXBAVRIYDKLCOE-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
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- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
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- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
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- 230000002028 premature Effects 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
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- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
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- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
ゲル浸透クロマトグラフィー(GPC):重量平均分子量(Mw)及び多分散指数を測定する:Mw及びMw/Mn比(多分散指数又はPDI)をPolymer Labs(商標)210高温ゲルパーミエーションクロマトグラフを用いて測定する。(ブチルヒドロキシトルエン(BHT)で安定化された)1,2,4−トリクロロベンゼン16mLで希釈されたポリエチレンポリマー13mgを用いて試料を調製し、160℃で2時間加熱し、振とうする。
ステップ1:3,6−ビス(1,1−ジメチルエチル)−9H−カルバゾールの調製
頭上式撹拌機、窒素ガスバブラー及び添加漏斗を備える500mL三口丸底フラスコに、カルバゾール20.02g(120.8mmol)、ZnCl2 49.82g(365.5mmol)及びニトロメタン300mLを室温で添加する。生成した暗褐色スラリーに2−クロロ−2−メチルプロパン49.82g(365.5mmol)を添加漏斗から2.5時間滴下する。添加終了後、生成したスラリーをさらに18時間撹拌する。反応混合物を氷冷水800mLに注ぎ、塩化メチレン3x500mLで抽出し、次いで抽出物を混合し、無水硫酸マグネシウムで脱水し、次いでろ過し、次いでろ液をまず回転蒸発によって、次いで高真空下の蒸発によって濃縮してニトロメタンを除去する。生成した残留物をまず高温の塩化メチレン(70mL)、続いて高温のヘキサン(50mL)に溶解させる。生成した溶液を室温に冷却し、次いで冷蔵庫に終夜放置する。形成された固体を単離し、冷ヘキサンで洗浄し、次いで高真空下で乾燥させて、オフホワイト結晶10.80g(32.0%)を得る。1H NMRによれば、生成物は所望の通りである。
ステップ2:2−ヨード−4−(2,4,4−トリメチルペンタン−2−イル)フェノールの調製
0℃のメタノール125mL中の4−(2,4,4−トリメチルペンタン−2−イル)フェノール10.30g(50.00mmol)の撹拌溶液にNaI7.48g(50.00mmol)及びNaOH2.00g(50mmol)を添加する。生成した混合物に5%NaOCl水溶液(市販漂白剤)86mLを1時間添加する。生成したスラリーを0℃でさらに1時間撹拌する。10%Na2S2O3水溶液(30mL)を添加し、希塩酸を添加して酸性化する。生成した混合物を塩化メチレンで抽出し、生成した有機層を塩水で洗浄し、無水硫酸マグネシウムで脱水する。揮発性物質を除去し、生成した残留物をシリカゲルを用いたフラッシュクロマトグラフィーによって、ヘキサン中の5体積パーセント(vol%)酢酸エチルで溶離させて精製し、生成物11.00g(66%)を粘ちゅう油として得る。1H NMRによれば、生成物は所望の通りである。
ステップ3:中間体2−(2−ヨード−4−(2,4,4−トリメチルペンタン−2−イル)フェノキシ)テトラヒドロ−2H−ピランの調製
0℃の塩化メチレン5mL中の4−(2,4,4−トリメチルペンタン−2−イル)フェノール4.91g(14.78mmol)及び3,4−ジヒドロピラン1.50g(17.83mmol)の撹拌溶液にパラ−トルエンスルホン酸一水和物0.039g(0.205mmol)を添加する。生成した溶液は、急速に紫色になる。溶液を室温に加温し、約10分間撹拌する。トリエチルアミンを添加すると(0.018g、0.178mmol)、生成した混合物は黄色になる。混合物を塩化メチレン50mLで希釈し、1M NaOH、水及び塩水各50mLで連続的に洗浄する。有機相を無水硫酸マグネシウムで脱水し、ろ過し、ろ液を濃縮して、粗製材料を得る。ヘキサン中の5vol%酢酸エチルを用いたシリカゲルフラッシュクロマトグラフィーによって粗製材料を精製して、生成物5.18g(93.12%)を金色油として得る。1H NMRによれば、生成物は所望の通りである。
ステップ4:中間体3,6−ジ−tert−ブチル−9−(2−(テトラヒドロ−2H−ピラン−2−イルオキシ)−5−(2,4,4−トリメチルペンタン−2−イル)フェニル)−9H−カルバゾールの調製
N2雰囲気下で撹拌棒及び凝縮器を備える50mL三口丸底フラスコに無水トルエン20mL、2−(2−ヨード−4−(2,4,4−トリメチルペンタン−2−イル)フェノキシ)テトラヒドロ−2H−ピラン5.00g(12.01mmol)、ジ−t−ブチルカルバゾール1)3.56g(12.01mmol)、CuI0.488g(2.56mmol)、K3PO4 7.71g(36.22mmol)、及びN,N’−ジメチルエチレンジアミン0.338g(3.84mmol)を添加する。反応混合物を48時間還流させ、冷却し、シリカゲル層を通してろ過し、次いでシリカゲルをテトラヒドロフラン(THF)でリンスし、有機物を濃縮して粗製残留物を得る。粗製残留物をアセトニトリルから結晶化させて、生成物4.57g(67.01%)を白色固体として得る。1H NMRによれば、生成物は所望の通りである。
ステップ5:1,2−ビス(4−フルオロ−2−ヨード−6−メチルフェノキシ)エタンの調製
N2雰囲気下の丸底フラスコに2−ヨード−4−フルオロ−6−メチルフェノール10.33g(40.99mmol)、K2CO3 11.34g(82.05mmol)、DMF80mL及び(Aldrichから得られる)エチレングリコールジトシラート7.59g(20.49mmol)を添加する。反応混合物を撹拌し、18時間還流させ、冷却し、濃縮する。すべての固体が溶解するまで残留物を50/50塩化メチレン/水で処理し、次いで混合物を分離漏斗に移し、化合物を塩化メチレンに抽出する。有機溶液を2N NaOH、水、次いで塩水で洗浄し、無水硫酸マグネシウムで脱水し、シリカゲルパッドを通してろ過し、濃縮して、白色固体9.93g(91.4%)を得る。1H NMRによれば、生成物は所望の通りである。
ステップ6:2’,2’’’−(エタン−1,2−ジイルビス(オキシ))ビス(3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−5’−フルオロ−3’−メチル−5−(2,4,4−トリメチルペンタン−2−イル)−[1,1’−ビフェニル]−2−オール)の調製
窒素雰囲気下の0℃のテトラヒドロフラン75mL中の3,6−ジ−tert−ブチル−9−(2−(メトキシメトキシ)−5−(2,4,4−トリメチルペンタン−2−イル)フェニル)−9H−カルバゾール5.0g(8.82mmol)の撹拌溶液にn−ブチルリチウム(2.5Mヘキサン溶液)8.1mL(20.25mmol)を10分間添加する。溶液を0℃でさらに3時間撹拌する。これにトリ−イソプロピルボラート(4.8mL、20.8mmol)を添加し、撹拌を0℃で1時間続ける。混合物を室温に徐々に加温し、室温でさらに3時間撹拌する。反応混合物を回転蒸発によって濃縮乾固させ、氷冷水100mLを添加する。混合物を2N塩酸を用いて酸性化し、塩化メチレンで抽出する。塩化メチレン溶液を水及び塩水で洗浄する。溶媒を回転蒸発によって除去し、残留物をジメトキシエタン90mLに溶解させる。次いで、この溶液を水25mL中のNaOH1.06g(26.5mmol)溶液、テトラヒドロフラン25mL及び1,2−ビス(4−フルオロ−2−ヨード−6−メチルフェノキシ)エタン2.2g(4.15mmol)で処理する。系を窒素パージし、Pd(PPh3)4 0.30g(0.26mmol)を添加した。次いで、混合物を窒素雰囲気下で85℃に36時間加熱する。沈殿生成物をろ過収集する。こうして得られた固体を塩化メチレンに溶解させ、塩水で洗浄し、無水硫酸マグネシウムで脱水する。溶媒除去後、反応生成物をTHF/MeOH(1:1)150mLに溶解させ、PTSA100mg添加後50℃で5時間撹拌する。溶媒を除去し、得られた固体をヘキサン中の10%酢酸エチル300mLに溶解させる。この溶液を小さいシリカゲル層に通す。溶媒除去後、減圧乾燥して、純粋な配位子4.65g(85%)を白色固体として得る。1H NMRによれば、生成物は所望の通りである。
ステップ7:1,2−ビス(4−フルオロ−2−ヨードフェノキシ)エタンの調製
N2雰囲気下の丸底フラスコに2−ヨード−4−フルオロフェノール3.00g(12.61mmol)、K2CO3 3.49g(25.25mmol)、DMF25mL及びエチレングリコールジトシラート2.34g(6.32mmol)を添加する。反応混合物を18時間還流させ、冷却し、濃縮した。すべての固体が溶解するまで残留物を50/50塩化メチレン/水で処理し、次いで混合物を分離漏斗に移し、化合物を塩化メチレンに抽出した。有機溶液を2N NaOH、水、次いで塩水で洗浄し、無水硫酸マグネシウムで脱水し、シリカゲルパッドを通してろ過し、濃縮して、純粋な架橋化合物(1,2−ビス(4−フルオロ−2−ヨードフェノキシ)エタン)3.07g(97.0%)を白色固体として得た。1H NMRによれば、生成物は所望の通りである。
ステップ8:6’,6’’’−(エタン−1,2−ジイルビス(オキシ))ビス(3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−3’−フルオロ−5−(2,4,4−トリメチルペンタン−2−イル)−[1,1’−ビフェニル]−2−オール)の調製
窒素雰囲気下の0℃のテトラヒドロフラン40mL中の3,6−ジ−tert−ブチル−9−(2−(メトキシメトキシ)−5−(2,4,4−トリメチルペンタン−2−イル)フェニル)−9H−カルバゾール2.5g(4.41mmol)の撹拌溶液にn−ブチルリチウム(2.5Mヘキサン溶液)4.05mL(10.12mmol)を10分間添加する。溶液を0℃でさらに3時間撹拌する。これにトリ−イソプロピルボラート(2.4mL、10.4mmol)を添加し、撹拌を0℃で1時間続ける。混合物を室温に徐々に加温し、室温でさらに3時間撹拌する。反応混合物を回転蒸発によって濃縮乾固させ、氷冷水100mLを添加する。混合物を2N塩酸を用いて酸性化し、塩化メチレンで抽出する。塩化メチレン溶液を水及び塩水で洗浄する。溶媒を回転蒸発によって除去し、残留物をジメトキシエタン50mLに溶解させる。次いで、この溶液を水15mL中のNaOH0.53g(13.25mmol)溶液、テトラヒドロフラン15mL及び1,2−ビス(4−フルオロ−2−ヨードフェノキシ)エタン1.05g(2.09mmol)で処理する。系を窒素パージし、Pd(PPh3)4 0.15g(0.13mmol)を添加する。次いで、混合物を窒素雰囲気下で85℃に36時間加熱する。反応混合物を冷却し、揮発性物質を回転蒸発によって除去する。残留物を水100mLで処理し、塩化メチレンで抽出する。塩化メチレン溶液を水及び塩水で洗浄し、無水硫酸マグネシウムで脱水する。溶媒除去後、反応生成物をTHF/MeOH(1:1)100mLに溶解させ、PTSA50mg添加後50℃で5時間撹拌する。溶媒を除去し、生成物をフラッシュクロマトグラフィーによってヘキサン中の5%酢酸エチルで溶離させて精製し、配位子2.2g(82.4%)を白色固体として得る。1H NMRによれば、生成物は所望の通りである。
ステップ9:(6’,6’’−(エタン−1,2−ジイルビス(オキシ))ビス(3’−フルオロ−3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−5−(2,4,4−トリメチルペンタン−2−イル)ビフェニル)ジメチル−ハフニウム(金属−配位子錯体1)の調製
トルエン35mLに懸濁された6’,6’’’−(エタン−1,2−ジイルビス(オキシ))ビス(3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−3’−フルオロ−5−(2,4,4−トリメチルペンタン−2−イル)−[1,1’−ビフェニル]−2−オール)1.571g(1.29mmol)及びHfCl4 0.415g(1.29mmol)にMeMgBrの3Mジエチルエーテル溶液1.94mL(5.82mmol)を添加する。周囲温度で2時間撹拌後、溶媒を減圧除去する。残留物にトルエン20mL及びヘキサン30mLを添加し、懸濁液をろ過する。溶媒を減圧除去すると、オフホワイト固体が残る。残留物にヘキサン30mLを添加し、懸濁液を20分間撹拌する。白色固体をフリット上に収集し、冷ヘキサン4mLで洗浄し、減圧乾燥させて、生成物1.07gを得る。ろ液を冷凍庫(−30℃)に3日間入れる。溶媒の上澄みを流し、生成した結晶を冷ヘキサン(2x3mL)で洗浄し、減圧乾燥させて追加の材料345mgを得る。混合収率1.415g(77%)。1H NMRによれば、生成物は所望の通りである。
代替ステップ9:(6’,6’’−(エタン−1,2−ジイルビス(オキシ))ビス(3’−フルオロ−3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−5−(2,4,4−トリメチルペンタン−2−イル)ビフェニル)ジメチル−ジルコニウム(金属−配位子錯体*2。*この錯体に関する更なるデータは下記実施例には含まれていない)の調製
トルエン50mL中の6’,6’’’−(エタン−1,2−ジイルビス(オキシ))ビス(3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−3’−フルオロ−5−(2,4,4−トリメチルペンタン−2−イル)−[1,1’−ビフェニル]−2−オール)(1.989g、1.64mmol)とZrCl4(0.382g、1.64mmol)の混合物にジエチルエーテル中のMeMgBrの3M溶液2.57mLを添加する。1時間撹拌後、溶媒を減圧除去する。残留物にトルエン30mL、続いてヘキサン30mLを添加し、溶液をろ過して、無色溶液を得る。溶媒を減圧除去し、無色固体を得る。この固体にヘキサン20mLを添加して、残留物を溶解させる。溶媒を減圧除去する。残留物にヘキサン15mLを添加し、懸濁液を1時間撹拌する。固体をフリット上に収集し、冷ヘキサン5mLで洗浄し、減圧乾燥させて、生成物1.223gを得る。収率56.0%。1H NMRによれば、生成物は所望の通りである。
代替ステップ9:(2’,2’’−(エタン−1,2−ジイルビス(オキシ))ビス(5’−フルオロ−3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−3’−メチル−5−(2,4,4−トリメチルペンタン−2−イル)ビフェニル−2−オール)ジメチル−ハフニウム(金属−配位子錯体3)の調製
トルエン70mL中の2’,2’’’−(エタン−1,2−ジイルビス(オキシ))ビス(3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−5’−フルオロ−3’−メチル−5−(2,4,4−トリメチルペンタン−2−イル)−[1,1’−ビフェニル]−2−オール)(3.03g、2.44mmol)及びHfCl4(0.782g、2.44mmol)の冷(−25℃)懸濁液にMeMgBrの3Mジエチルエーテル溶液3.5mL(10.5mmol)を添加する。1時間撹拌後、溶媒を減圧除去する。残留物にトルエン20mL、続いてヘキサン30mLを添加する。懸濁液をろ過して、灰色溶液を得る。溶媒を減圧除去すると、淡灰色固体が残る。残留物をヘキサン8mLに懸濁させ、懸濁液を30分間撹拌する。固体をフリット上に収集し、ヘキサン3mLで洗浄し、減圧乾燥させて、生成物2.87gをオフホワイト固体として得る。収率は81.2%である。1H NMRによれば、生成物は所望の通りである。
代替ステップ9:(2’,2’’−(エタン−1,2−ジイルビス(オキシ))ビス(5’−フルオロ−3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−3’−メチル−5−(2,4,4−トリメチルペンタン−2−イル)ビフェニル−2−オール)ジメチル−ジルコニウム(金属−配位子錯体4)の調製
トルエン50mL中の2’,2’’’−(エタン−1,2−ジイルビス(オキシ))ビス(3−(3,6−ジ−tert−ブチル−9H−カルバゾル−9−イル)−5’−フルオロ−3’−メチル−5−(2,4,4−トリメチルペンタン−2−イル)−[1,1’−ビフェニル]−2−オール)(0.75g、0.59mmol)及びZrCl4(0.137g、0.59mmol)の懸濁液にMeMgBrの3Mジエチルエーテル溶液0.84mL(2.53mmol)を添加する。1時間撹拌後、溶媒を減圧除去する。残留物にトルエン20mL、続いてヘキサン30mLを添加する。懸濁液をろ過して、無色溶液を得る。溶媒を減圧除去すると、白色固体が残る。残留物をヘキサン15mLに懸濁させ、懸濁液を30分間撹拌する。固体をフリット上に収集し、ヘキサン3mLで洗浄し、減圧乾燥させて、生成物0.545gを白色固体として得る。収率は66.5%である。1H NMRによれば、生成物は所望の通りである。
重合を2L Parr(商標)回分式反応器中で実施する。反応器を電気加熱マントルで加熱し、冷却水を含む内部蛇行冷却コイルで冷却する。反応器と加熱/冷却系の両方をCamile(商標)TGプロセスコンピュータによって制御し、監視する。反応器の底部には放出弁が取り付けられている。放出弁は、反応器内容物をステンレス鋼(SS)放出ポットに空ける。放出ポットには、触媒失活溶液(一般に、IRGAFOX(商標)/IRGANOX(商標)/トルエン混合物5mL)があらかじめ充填されている。放出ポットは30ガロンブロータンクに通じており、ポットとタンクの両方はN2パージされている。重合に使用されるすべての化学物質又は触媒補充物を精製カラムに通して、重合に影響し得る不純物を除去する。1−オクテンを2本のカラムに通す。第1のカラムはAl2O4アルミナを含み、第2のカラムは酸素を除去するQ5反応物を含む。エチレンも2本のカラムに通す。第1のカラムはAl2O4アルミナ及び孔径4オングストローム(Å)のモレキュラーシーブを含み、第2のカラムはQ5反応物を含む。移送に使用されるN2は、Al2O4アルミナ、孔径4Åのモレキュラーシーブ及びQ5反応物を含む単一カラムを通過する。
重合手順並びに金属−配位子錯体1、3及び4の金属−配位子錯体合成手順を使用して、エチレンと1−オクテンを共重合して、ポリ(コ−エチレン−α−オレフィン)誘電性流体組成物を形成する。重合条件、活性化共触媒の識別、及び結果を以下の表1に示す。
活性化物質:[HNMe(C18H37)2][B(C6F5)4];MMAO15モル;反応時間10min
重合手順及び金属−配位子錯体3合成プロセスを使用してエチレンと1−オクテンを再度共重合する。条件及び活性化共触媒の識別を以下の表3に示す。本発明の誘電性流体組成物を特徴づける広範な異性体形成の一実施形態を示すGCクロマトグラフィー分析を図1に示す。
Claims (9)
- ポリ−α−オレフィン及びポリ(コ−エチレン−α−オレフィン)から選択される生成物が形成される条件下で、(1)(a)α−オレフィン又は(b)α−オレフィンとエチレンとの組合せから選択されるモノマーと(2)触媒作用量の触媒を接触させるステップを含むプロセスから調製される、重量平均分子量が200ダルトン(Da)を超え10,000ダルトン(Da)未満であるポリ−α−オレフィン又はポリ(コ−エチレン/α−オレフィン)を含む、誘電性流体組成物であって、前記触媒が、前記接触ステップ前に調製される成分(2a)と(2b)との混合物又は反応生成物を含み、成分(2a)が式(I)の少なくとも1種類の金属−配位子錯体であり、成分(2b)が少なくとも1種類の活性化共触媒であり、前記少なくとも1種類の金属−配位子錯体(2a)の全モル数と前記少なくとも1種類の活性化共触媒(2b)の全モル数との比は1:10,000から100:1であり、前記生成物の分子量分布成分及び骨格重量平均分子量(Mw)が200Daを超え10,000Da未満であり、前記生成物が300Daを超える各分布成分中に少なくとも2種類の異性体を含む、誘電性流体組成物
- 前記重量平均分子量が1500ダルトン未満である、請求項1に記載の誘電性組成物。
- 各ZがOである、請求項1又は2のいずれか一項に記載の誘電性組成物。
- R1a及びR1bがメチル、エチル又はイソプロピルである、請求項1から3のいずれか一項に記載の誘電性組成物。
- R1a及びR1bがフッ素原子、塩素原子、臭素原子又はヨウ素原子である、請求項1から4のいずれか一項に記載の誘電性組成物。
- Lが−CH2CH2−、−CH(CH3)CH(CH3)−、1,2−シクロペンタン−ジイル又は1,2−シクロヘキサン−ジイルである、請求項1から5のいずれか一項に記載のプロセス。
- R5dが、独立に、2,7−二置換9H−カルバゾル−9−イル又は3,6−二置換9H−カルバゾル−9−イル、9H−カルバゾル−9−イルであり、各置換基がRSである、請求項1から6のいずれか一項に記載の誘電性組成物。
- R5dが、独立に、各置換基がRSである2,4−二置換フェニル;各置換基がRSである2,5−二置換フェニル;各置換基がRSである2,6−二置換フェニル;各置換基がRSである3,5−二置換フェニル;各置換基がRSである2,4,6−三置換フェニル;ナフチル、又は各置換基がRSである置換ナフチル;1,2,3,4−テトラヒドロナフチル;アントラセニル;1,2,3,4−テトラヒドロ−アントラセニル;1,2,3,4,5,6,7,8−オクタヒドロアントラセニル;フェナントレニル;又は1,2,3,4,5,6,7,8−オクタヒドロフェン−アントレニルである(C6−C40)アリールである、請求項1から7のいずれか一項に記載の誘電性組成物。
- 前記条件が40℃から300℃の範囲の温度を含む、請求項1から8のいずれか一項に記載の誘電性組成物。
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JP2021507882A (ja) * | 2017-12-21 | 2021-02-25 | サビック エスケー ネクスレン カンパニー ピーティーイー リミテッド | 金属−リガンド錯体、これを含むエチレン系重合用の触媒組成物およびこれを用いたエチレン系重合体の製造方法 |
JP7163389B2 (ja) | 2017-12-21 | 2022-10-31 | サビック エスケー ネクスレン カンパニー ピーティーイー リミテッド | 金属-リガンド錯体、これを含むエチレン系重合用の触媒組成物およびこれを用いたエチレン系重合体の製造方法 |
JP2021534281A (ja) * | 2018-08-30 | 2021-12-09 | ダウ グローバル テクノロジーズ エルエルシー | 2つのアントラセニル配位子を有するビス−フェニル−フェノキシポリオレフィンプロ触媒 |
JP7460602B2 (ja) | 2018-08-30 | 2024-04-02 | ダウ グローバル テクノロジーズ エルエルシー | 2つのアントラセニル配位子を有するビス-フェニル-フェノキシポリオレフィンプロ触媒 |
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CA2861516C (en) | 2021-01-05 |
US20140330056A1 (en) | 2014-11-06 |
EP2797963A1 (en) | 2014-11-05 |
TWI552166B (zh) | 2016-10-01 |
WO2013101376A1 (en) | 2013-07-04 |
KR20140107318A (ko) | 2014-09-04 |
CN104024285A (zh) | 2014-09-03 |
KR101988690B1 (ko) | 2019-06-12 |
CN104024285B (zh) | 2017-03-22 |
MX2014007931A (es) | 2014-11-25 |
EP2797963B1 (en) | 2019-07-03 |
TW201337961A (zh) | 2013-09-16 |
BR112014015971A8 (pt) | 2017-07-04 |
JP6117822B2 (ja) | 2017-04-19 |
CA2861516A1 (en) | 2013-07-04 |
BR112014015971A2 (pt) | 2017-06-13 |
US9601231B2 (en) | 2017-03-21 |
BR112014015971B1 (pt) | 2021-05-18 |
MX368963B (es) | 2019-10-23 |
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