JP3900698B2

JP3900698B2 - オレフィン重合用触媒およびオレフィンの重合方法

オレフィン重合用触媒およびオレフィンの重合方法 Download PDF

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Publication number: JP3900698B2
Authority: JP; Japan
Prior art keywords: group; compound; groups; carbon atoms; magnesium
Prior art date: 1998-08-12
Legal status : Expired - Lifetime

Application number

JP22799198A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000063416A5 (https=

JP2000063416A (ja

Inventor

藤純治斎

谷誠三

田照典藤

Current Assignee

Mitsui Chemicals Inc

Original Assignee

Mitsui Chemicals Inc

Priority date

1998-08-12

Filing date

1998-08-12

Publication date

2007-04-04

1998-08-12 Application filed by Mitsui Chemicals Inc filed Critical Mitsui Chemicals Inc

1998-08-12 Priority to JP22799198A priority Critical patent/JP3900698B2/ja

2000-02-29 Publication of JP2000063416A publication Critical patent/JP2000063416A/ja

2005-05-19 Publication of JP2000063416A5 publication Critical patent/JP2000063416A5/ja

2007-04-04 Application granted granted Critical

2007-04-04 Publication of JP3900698B2 publication Critical patent/JP3900698B2/ja

2018-08-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 58
238000006116 polymerization reaction Methods 0.000 title claims description 43
150000001336 alkenes Chemical class 0.000 title claims description 39
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 38
239000002685 polymerization catalyst Substances 0.000 title claims description 16
-1 oxy compound Chemical class 0.000 claims description 192
125000004432 carbon atom Chemical group C* 0.000 claims description 114
150000001875 compounds Chemical class 0.000 claims description 114
125000001183 hydrocarbyl group Chemical group 0.000 claims description 92
239000010936 titanium Substances 0.000 claims description 90
239000003054 catalyst Substances 0.000 claims description 68
229910052719 titanium Inorganic materials 0.000 claims description 61
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 59
150000003623 transition metal compounds Chemical class 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 41
150000002367 halogens Chemical class 0.000 claims description 41
125000005843 halogen group Chemical group 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
239000011777 magnesium Substances 0.000 claims description 22
229910052749 magnesium Inorganic materials 0.000 claims description 21
230000000737 periodic effect Effects 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 18
150000003624 transition metals Chemical group 0.000 claims description 18
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 17
150000008040 ionic compounds Chemical class 0.000 claims description 13
230000000379 polymerizing effect Effects 0.000 claims description 3
150000002681 magnesium compounds Chemical class 0.000 description 49
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229910052710 silicon Inorganic materials 0.000 description 44
239000010703 silicon Substances 0.000 description 42
229910052760 oxygen Inorganic materials 0.000 description 37
229910052717 sulfur Inorganic materials 0.000 description 37
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 36
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239000011574 phosphorus Substances 0.000 description 27
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239000002184 metal Substances 0.000 description 26
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239000002253 acid Substances 0.000 description 23
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150000002391 heterocyclic compounds Chemical group 0.000 description 14
239000007787 solid Substances 0.000 description 14
239000004215 Carbon black (E152) Substances 0.000 description 13
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125000004429 atom Chemical group 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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239000000126 substance Substances 0.000 description 12
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125000003545 alkoxy group Chemical group 0.000 description 11
239000004927 clay Substances 0.000 description 11
239000002734 clay mineral Substances 0.000 description 11
238000009826 distribution Methods 0.000 description 11
239000003446 ligand Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
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238000002360 preparation method Methods 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 10
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
229920000642 polymer Polymers 0.000 description 10
230000037048 polymerization activity Effects 0.000 description 10
230000001603 reducing effect Effects 0.000 description 10
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 10
125000005234 alkyl aluminium group Chemical group 0.000 description 9
150000002500 ions Chemical class 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
229920000573 polyethylene Polymers 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000004122 cyclic group Chemical group 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
125000005842 heteroatom Chemical group 0.000 description 8
125000005647 linker group Chemical group 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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229920000098 polyolefin Polymers 0.000 description 8
229910052723 transition metal Inorganic materials 0.000 description 8
239000004698 Polyethylene Substances 0.000 description 7
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 7
150000001768 cations Chemical class 0.000 description 7
239000013078 crystal Substances 0.000 description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
229910052735 hafnium Inorganic materials 0.000 description 7
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 7
XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 7
239000010948 rhodium Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
229910052726 zirconium Inorganic materials 0.000 description 7
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239000005977 Ethylene Substances 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
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239000007795 chemical reaction product Substances 0.000 description 6
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229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229910001629 magnesium chloride Inorganic materials 0.000 description 6
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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239000010941 cobalt Substances 0.000 description 4
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229910052785 arsenic Inorganic materials 0.000 description 3
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239000012298 atmosphere Substances 0.000 description 3
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
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SYLAFCZSYRXBJF-UHFFFAOYSA-N furan-3,4-dicarboxylic acid Chemical compound OC(=O)C1=COC=C1C(O)=O SYLAFCZSYRXBJF-UHFFFAOYSA-N 0.000 description 1
JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
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PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
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 1
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230000003301 hydrolyzing effect Effects 0.000 description 1
DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical group [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
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RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
239000011229 interlayer Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
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150000002537 isoquinolines Chemical class 0.000 description 1
ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
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XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
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QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 description 1
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RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
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NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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150000003682 vanadium compounds Chemical class 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
229940117958 vinyl acetate Drugs 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
229910006592 α-Sn Inorganic materials 0.000 description 1