JP6153278B2 - リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 - Google Patents
リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 Download PDFInfo
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- JP6153278B2 JP6153278B2 JP2016516470A JP2016516470A JP6153278B2 JP 6153278 B2 JP6153278 B2 JP 6153278B2 JP 2016516470 A JP2016516470 A JP 2016516470A JP 2016516470 A JP2016516470 A JP 2016516470A JP 6153278 B2 JP6153278 B2 JP 6153278B2
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- carbon atoms
- olefin oligomerization
- chromium
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- 150000001336 alkenes Chemical class 0.000 title claims description 51
- 150000001875 compounds Chemical class 0.000 title claims description 48
- 239000003446 ligand Substances 0.000 title claims description 47
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 47
- 239000003054 catalyst Substances 0.000 title claims description 42
- 238000006384 oligomerization reaction Methods 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 31
- 239000005977 Ethylene Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 229910052723 transition metal Inorganic materials 0.000 claims description 10
- 150000003624 transition metals Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- XYQQGESWGNLKIO-UHFFFAOYSA-N acetic acid;chromium;dihydrate Chemical compound O.O.[Cr].[Cr].[Cr].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O XYQQGESWGNLKIO-UHFFFAOYSA-N 0.000 claims description 2
- GWKHNQIALWXRPA-GECNZSFWSA-N chromium (Z)-5-hydroxy-2,2,6,6-tetramethylhept-4-en-3-one (E)-5-hydroxy-2,2,6,6-tetramethylhept-4-en-3-one Chemical compound [Cr].CC(C)(C)C(\O)=C/C(=O)C(C)(C)C.CC(C)(C)C(\O)=C/C(=O)C(C)(C)C.CC(C)(C)C(\O)=C\C(=O)C(C)(C)C GWKHNQIALWXRPA-GECNZSFWSA-N 0.000 claims description 2
- WUZCBSQKHJJABD-YNEVXYPXSA-K chromium(3+);(z)-3-oxo-1-phenylbut-1-en-1-olate Chemical compound [Cr+3].CC(=O)\C=C(/[O-])C1=CC=CC=C1.CC(=O)\C=C(/[O-])C1=CC=CC=C1.CC(=O)\C=C(/[O-])C1=CC=CC=C1 WUZCBSQKHJJABD-YNEVXYPXSA-K 0.000 claims description 2
- CYOMBOLDXZUMBU-UHFFFAOYSA-K chromium(3+);oxolane;trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3].C1CCOC1.C1CCOC1.C1CCOC1 CYOMBOLDXZUMBU-UHFFFAOYSA-K 0.000 claims description 2
- 150000007527 lewis bases Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- WBKDDMYJLXVBNI-UHFFFAOYSA-K chromium(3+);2-ethylhexanoate Chemical compound [Cr+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O WBKDDMYJLXVBNI-UHFFFAOYSA-K 0.000 claims 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 239000011651 chromium Substances 0.000 description 19
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
- -1 polyethylene Polymers 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 11
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- 229910052804 chromium Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical class C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 6
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229920000092 linear low density polyethylene Polymers 0.000 description 5
- 239000004707 linear low-density polyethylene Substances 0.000 description 5
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 5
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 4
- 0 *P(*)N(P(*)I)I Chemical compound *P(*)N(P(*)I)I 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DXQXWMYUGOTNGJ-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boron Chemical compound [B]C1=CC=C(C(F)(F)F)C=C1 DXQXWMYUGOTNGJ-UHFFFAOYSA-N 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 3
- GWUXLTRGPPIDJA-UHFFFAOYSA-N (4-methylphenyl)alumane Chemical compound CC1=CC=C([AlH2])C=C1 GWUXLTRGPPIDJA-UHFFFAOYSA-N 0.000 description 2
- VKMQKNJWQNCEQV-UHFFFAOYSA-N (4-methylphenyl)boron Chemical compound [B]C1=CC=C(C)C=C1 VKMQKNJWQNCEQV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- SHGOGDWTZKFNSC-UHFFFAOYSA-N ethyl(dimethyl)alumane Chemical compound CC[Al](C)C SHGOGDWTZKFNSC-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CLTXLGPSIXHRDP-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1,3-diamine Chemical compound C1=CC=C2C(N)CC(N)C2=C1 CLTXLGPSIXHRDP-UHFFFAOYSA-N 0.000 description 1
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
- ZGMQLPDXPUINCQ-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-amine Chemical compound CC1CC(N)CC(C)(C)C1 ZGMQLPDXPUINCQ-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YOCRSFAAPYYJLT-UHFFFAOYSA-N C(C)B(CC)CC.CB(C)C Chemical compound C(C)B(CC)CC.CB(C)C YOCRSFAAPYYJLT-UHFFFAOYSA-N 0.000 description 1
- PLGVIJOQDDMWAO-UHFFFAOYSA-N CCCCN(CCCC)CCCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F Chemical compound CCCCN(CCCC)CCCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F PLGVIJOQDDMWAO-UHFFFAOYSA-N 0.000 description 1
- JEVCOCKVSCRHMR-UHFFFAOYSA-N CCN(CC)C1=CC=CC=C1.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F Chemical compound CCN(CC)C1=CC=CC=C1.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F JEVCOCKVSCRHMR-UHFFFAOYSA-N 0.000 description 1
- HFEVWLDHPOCPTP-UHFFFAOYSA-N CCNCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F Chemical compound CCNCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F HFEVWLDHPOCPTP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- SHPVKUQHCZKKRP-UHFFFAOYSA-N [B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.CCCCN(CCCC)CCCC Chemical compound [B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.CCCCN(CCCC)CCCC SHPVKUQHCZKKRP-UHFFFAOYSA-N 0.000 description 1
- XIBZTAIPROXEDH-UHFFFAOYSA-N [B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.CCN(CC)C1=CC=CC=C1 Chemical compound [B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.CCN(CC)C1=CC=CC=C1 XIBZTAIPROXEDH-UHFFFAOYSA-N 0.000 description 1
- RPXNIXOOFOQCKJ-UHFFFAOYSA-N [B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.CCNCC Chemical compound [B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.[B+2]C(C(F)=C(C(F)=C1F)F)=C1F.CCNCC RPXNIXOOFOQCKJ-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical group PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052787 antimony Chemical group 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MYBJXSAXGLILJD-UHFFFAOYSA-N diethyl(methyl)alumane Chemical compound CC[Al](C)CC MYBJXSAXGLILJD-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- ISEJRLXHKSHKPM-UHFFFAOYSA-N dimethyl(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)C ISEJRLXHKSHKPM-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- MWNKMBHGMZHEMM-UHFFFAOYSA-N dimethylalumanylium;ethanolate Chemical compound CCO[Al](C)C MWNKMBHGMZHEMM-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910021482 group 13 metal Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BQBCXNQILNPAPX-UHFFFAOYSA-N methoxy(dimethyl)alumane Chemical compound [O-]C.C[Al+]C BQBCXNQILNPAPX-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical compound [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- NDUUEFPGQBSFPV-UHFFFAOYSA-N tri(butan-2-yl)alumane Chemical compound CCC(C)[Al](C(C)CC)C(C)CC NDUUEFPGQBSFPV-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- PYLGJXLKFZZEBJ-UHFFFAOYSA-N tricyclopentylalumane Chemical compound C1CCCC1[Al](C1CCCC1)C1CCCC1 PYLGJXLKFZZEBJ-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- ZMPKTELQGVLZTD-UHFFFAOYSA-N tripropylborane Chemical compound CCCB(CCC)CCC ZMPKTELQGVLZTD-UHFFFAOYSA-N 0.000 description 1
- XDSSGQHOYWGIKC-UHFFFAOYSA-N tris(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)CC(C)C XDSSGQHOYWGIKC-UHFFFAOYSA-N 0.000 description 1
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
前記2以上のグループの間をそれぞれ4個の炭素原子で連結するグループであって、
炭素数1〜20の脂肪族グループと、
炭素数3〜20の脂環族グループおよび炭素数6〜20の芳香族グループからなる群より選択されたグループとが結合されたグループを有するリガンド化合物を提供する。
前記2以上のグループの間をそれぞれ4個の炭素原子で連結するグループであって、
炭素数1〜20の脂肪族グループと、
炭素数3〜20の脂環族グループおよび炭素数6〜20の芳香族グループからなる群より選択されたグループとが結合されたグループを有するリガンド化合物が提供される。
Dは、アルミニウムまたはボロンであり、R6は、互いに同一または異なり、それぞれ独立に、水素またはハロゲン、炭素数1〜20のヒドロカルビル、またはハロゲンで置換された炭素数1〜20のヒドロカルビルであり、
Lは、中性ルイス塩基であり、[L−H]+は、ブレンステッド酸であり、Qは、+3形式酸化状態のホウ素またはアルミニウムであり、Eは、それぞれ独立に、1以上の水素原子がハロゲン、炭素数1〜20のヒドロカルビル、アルコキシ官能基、またはフェノキシ官能基で置換もしくは非置換の炭素数6〜20のアリール基、または炭素数1〜20のアルキル基である。
全ての反応は、Schlenk techniqueやglove boxを用いて、アルゴン下で行われた。合成されたリガンドは、Varian 500MHz spectrometerを用いて、1H(500MHz)と31P(202MHz)NMR spectraを撮って分析した。Shiftは、residual solvent peakをreferenceとして、TMSからdownfieldでppmで示した。Phosphorous probeは、aqueous H3PO4でcalibrationした。
(段階1)
アルゴンガス下、Cr(acac)3(17.5mg、0.05mmol)と、前記実施例1により製造されたリガンド化合物(0.025mmol)をフラスコに入れて、10mlのシクロヘキサンを添加し撹拌して、5mM(Cr基準)溶液を製造した。
600ml容量のParr反応器を準備して、120℃で2時間真空を取った後、内部をアルゴンに置換し、温度を45℃に下げた。その後、90mlのシクロヘキサン、およびMMAO(イソヘプタン溶液、Al/Cr=1200)2mlを注入し、前記5mM溶液0.5ml(2.5umol)を反応器に注入した。2分間500rpmで撹拌後、45barに合わされたエチレンラインのバルブを開けて反応器中をエチレンで満たした後、45℃に制熱されるように調節して、500rpmで15分間撹拌した。エチレンラインのバルブを閉じ、反応器をドライアイス/アセトンbathを用いて0℃に冷やした後、未反応エチレンをゆっくりvent後、ノナン(GC internal standard)を0.5ml入れた。10秒間撹拌後、反応器の液体部分を2ml取って水でquenchし、有機層をPTFEシリンジフィルタでフィルタして、GC分析を行った。
残りの反応液にエタノール/HCl(10vol%)400mlを入れて撹拌しフィルタリングして、ポリマーを得た。得られたポリマーは、65℃のvacuumオーブンで一晩乾燥し、重量を測定した。
(段階1)
アルゴンガス下、Cr(acac)3(17.5mg、0.05mmol)と、前記実施例1により製造されたリガンド化合物(0.025mmol)をフラスコに入れて、100mlのメチルシクロヘキサンを添加し撹拌して、0.5mM(Cr基準)溶液を製造した。
600ml容量のParr反応器を準備して、120℃で2時間真空を取った後、内部をアルゴンに置換し、温度を60℃に下げた。その後、175mlのメチルシクロヘキサン、およびMMAO(イソヘプタン溶液、Al/Cr=1200)2mlを注入し、前記0.5mM溶液5ml(2.5umol)を反応器に注入した。1分間500rpmで撹拌後、60barに合わされたエチレンラインのバルブを開けて反応器中をエチレンで満たした後、60℃に制熱されるように調節して、500rpmで15分間撹拌した。エチレンラインのバルブを閉じ、反応器をドライアイス/アセトンbathを用いて0℃に冷やした後、未反応エチレンをゆっくりvent後、ノナン(GC internal standard)を0.5ml入れた。10秒間撹拌後、反応器の液体部分を2ml取って水でquenchし、有機層をPTFEシリンジフィルタでフィルタして、GC分析を行った。
残りの反応液にエタノール/HCl(10vol%)400mlを入れて撹拌しフィルタリングして、ポリマーを得た。得られたポリマーは、65℃のvacuumオーブンで一晩乾燥し、重量を測定した。
(段階1)
窒素雰囲気下の1.5L CSTR反応器にシクロヘキサンとエチレンをそれぞれ2.34kg/hrおよび2.50kg/hrの流量で連続的に投入して、圧力が60barに維持されるようにした。10L圧力容器に、実施例1で製造したリガンドとCr(acac)3をリガンド:クロムが0.55:1のモル比となるように投入した後、シクロヘキサンで適宜希釈した触媒溶液を0.70μmol/minの速度で反応器に投入すると同時に、助触媒MMAOをシクロヘキサンで希釈した溶液をAl:Crが1200:1のモル比となるように触媒溶液の投入量に合わせて連続的に投入した。反応温度は、反応器Jacketに常温の水を連続的に投入して、90℃となるように調節した。2時間反応が安定的に進行する状況下、排出される反応物を1時間捕集し、5mLを取って水でquenchし、有機層をPTFEシリンジフィルタでフィルタして、GC分析を行った。
残りの反応液にエタノール/HCl(10vol%)4.0Lを入れて撹拌しフィルタリングして、ポリマーを得た。得られたポリマーは、65℃のvacuumオーブンで一晩乾燥し、重量を測定した。
前記実験例3と同様の方法で実施するものの、前記実験例3でシクロヘキサンおよびエチレンの流量をそれぞれ1.13kg/hrおよび1.40kg/hrに変更し、シクロヘキサンで希釈した触媒溶液を1.05μmol/minの速度で反応器に投入し、反応温度を103℃に変更して実施した。
前記実験例3と同様の方法で実施するものの、前記実験例3におけるシクロヘキサンおよびエチレンの流量をそれぞれ1.00kg/hrおよび1.30kg/hrに変更し、反応温度を102℃に変更して実施した。
(段階1)
アルゴンガス下、Cr(acac)3(17.5mg、0.05mmol)と、前記比較例1により製造されたリガンド化合物(0.025mmol)をフラスコに入れて、10mlのシクロヘキサンを添加し撹拌して、5mM(Cr基準)溶液を製造した。
600ml容量のParr反応器を準備して、120℃で2時間真空を取った後、内部をアルゴンに置換し、温度を45℃に下げた。その後、90mlのシクロヘキサン、およびMMAO(イソヘプタン溶液、Al/Cr=1200)2mlを注入し、前記5mM溶液0.5ml(2.5umol)を反応器に注入した。2分間500rpmで撹拌後、45barに合わされたエチレンラインのバルブを開けて反応器中をエチレンで満たした後、45℃に制熱されるように調節して、500rpmで15分間撹拌した。エチレンラインのバルブを閉じ、反応器をドライアイス/アセトンbathを用いて0℃に冷やした後、未反応エチレンをゆっくりvent後、ノナン(GC internal standard)を0.5ml入れた。10秒間撹拌後、反応器の液体部分を2ml取って水でquenchし、有機層をPTFEシリンジフィルタでフィルタして、GC分析を行った。
残りの反応液にエタノール/HCl(10vol%)400mlを入れて撹拌しフィルタリングして、ポリマーを得た。得られたポリマーは、65℃のvacuumオーブンで一晩乾燥し、重量を測定した。
前記比較実験例1と同様の方法で実施するものの、比較例1により製造されたリガンド化合物(0.025mmol)を、比較例2により製造されたリガンド化合物(0.025mmol)に変更して実施した。
(段階1)
アルゴンガス下、Cr(acac)3(17.5mg、0.05mmol)と、前記比較例2により製造されたリガンド化合物(0.025mmol)をフラスコに入れて、1000mlのメチルシクロヘキサンを添加し撹拌して、0.5mM(Cr基準)溶液を製造した。
600ml容量のParr反応器を準備して、120℃で2時間真空を取った後、内部をアルゴンに置換し、温度を60℃に下げた。その後、175mlのシクロヘキサン、およびMMAO(イソヘプタン溶液、Al/Cr=1200)2mlを注入し、前記0.5mM溶液5ml(2.5umol)を反応器に注入した。1分間500rpmで撹拌後、60barに合わされたエチレンラインのバルブを開けて反応器中をエチレンで満たした後、60℃に制熱されるように調節して、500rpmで15分間撹拌した。エチレンラインのバルブを閉じ、反応器をドライアイス/アセトンbathを用いて0℃に冷やした後、未反応エチレンをゆっくりvent後、ノナン(GC internal standard)を0.5ml入れた。10秒間撹拌後、反応器の液体部分を2ml取って水でquenchし、有機層をPTFEシリンジフィルタでフィルタして、GC分析を行った。
残りの反応液にエタノール/HCl(10vol%)400mlを入れて撹拌しフィルタリングして、ポリマーを得た。得られたポリマーは、65℃のvacuumオーブンで一晩乾燥し、重量を測定した。
前記比較実験例1と同様の方法で実施するものの、比較例1により製造されたリガンド化合物(0.025mmol)を、比較例3により製造されたリガンド化合物(0.025mmol)に変更して実施した。
前記実験例2と同様の方法で実施するものの、実施例1により製造されたリガンド化合物(0.025mmol)を、比較例4により製造されたリガンド化合物(0.025mmol)に変更して実施した。
(段階1)
アルゴンガス下、Cr(acac)3(17.5mg、0.05mmol)をフラスコに入れて、100mlのメチルシクロヘキサンを添加し撹拌して、0.5mM(Cr基準)溶液を製造した。
600ml容量のParr反応器を準備して、120℃で2時間真空を取った後、内部をアルゴンに置換し、温度を60℃に下げた。その後、175mlのシクロヘキサン、およびMMAO(イソヘプタン溶液、Al/Cr=1200)2mlを注入し、前記0.5mM溶液5ml(2.5umol)を反応器に注入した。1分間500rpmで撹拌後、60barに合わされたエチレンラインのバルブを開けて反応器中をエチレンで満たした後、60℃に制熱されるように調節して、500rpmで15分間撹拌した。エチレンラインのバルブを閉じ、反応器をドライアイス/アセトンbathを用いて0℃に冷やした後、未反応エチレンをゆっくりvent後、ノナン(GC internal standard)を0.5ml入れた。10秒間撹拌後、反応器の液体部分を2ml取って水でquenchし、有機層をPTFEシリンジフィルタでフィルタして、GC分析を行った。
残りの反応液にエタノール/HCl(10vol%)400mlを入れて撹拌しフィルタリングして、ポリマーを得た。得られたポリマーは、65℃のvacuumオーブンで一晩乾燥し、重量を測定した。
Claims (9)
- 分子内に下記化学式1で表されるグループを2以上含み、
前記2以上のグループの間をそれぞれ4個の炭素原子で連結するグループであって、下記化学式からなる群より選択されるグループを有するリガンド化合物。
- 前記化学式1のR1〜R4は、フェニルである請求項1に記載のリガンド化合物。
- 請求項1〜3のいずれか1項に記載のリガンド化合物、遷移金属供給源、および助触媒を含むオレフィンオリゴマー化用触媒系であって、
前記遷移金属供給源は、主触媒の役割を果たすもので、クロム(III)アセチルアセトネート、三塩化クロムトリステトラヒドロフラン、クロム(III)−2−エチルヘキサノエート、クロム(III)トリス(2,2,6,6−テトラメチル−3,5−ヘプタンジオネート)、クロム(III)ベンゾイルアセトネート、クロム(III)ヘキサフルオロ−2,4−ペンタンジオネート、およびクロム(III)アセテートヒドロキシドからなる群より選択されるいずれか1つ以上であるオレフィンオリゴマー化用触媒系。 - 前記助触媒は、下記化学式2〜4で表される化合物からなる群より選択された1種以上である請求項4に記載のオレフィンオリゴマー化用触媒系:
[化学式2]
−[Al(R5)−O]c−
前記化学式2において、R5は、互いに同一または異なり、それぞれ独立に、ハロゲンラジカル、炭素数1〜20のヒドロカルビルラジカル、またはハロゲンで置換された炭素数1〜20のヒドロカルビルラジカルであり、cは、2以上の整数であり、
[化学式3]
D(R6)3
前記化学式3において、
Dは、アルミニウムまたはボロンであり、R6は、互いに同一または異なり、それぞれ独立に、水素またはハロゲン、炭素数1〜20のヒドロカルビル、またはハロゲンで置換された炭素数1〜20のヒドロカルビルであり、
[化学式4]
[L−H]+[Q(E)4]-
前記化学式4において、
Lは、中性ルイス塩基であり、[L−H]+は、ブレンステッド酸であり、Qは、+3形式酸化状態のホウ素またはアルミニウムであり、Eは、それぞれ独立に、1以上の水素原子がハロゲン、炭素数1〜20のヒドロカルビル、アルコキシ官能基またはフェノキシ官能基で置換もしくは非置換の炭素数6〜20のアリール基、または炭素数1〜20のアルキル基である。 - 請求項4または5に記載のオレフィンオリゴマー化用触媒系の存在下、オレフィンを多量化反応させる段階を含むオレフィンオリゴマー化方法。
- 前記オレフィンは、エチレンである請求項6に記載のオレフィンオリゴマー化方法。
- 前記多量化反応温度は、5〜200℃である請求項6または7に記載のオレフィンオリゴマー化方法。
- 前記多量化反応圧力は、1〜300barである請求項6〜8のいずれか一項に記載のオレフィンオリゴマー化方法。
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