KR102288227B1 - 올레핀 중합용 촉매 시스템 - Google Patents

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Publication number

KR102288227B1

KR102288227B1 KR1020167019678A KR20167019678A KR102288227B1 KR 102288227 B1 KR102288227 B1 KR 102288227B1 KR 1020167019678 A KR1020167019678 A KR 1020167019678A KR 20167019678 A KR20167019678 A KR 20167019678A KR 102288227 B1 KR102288227 B1 KR 102288227B1

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KR

South Korea

Prior art keywords

group

formula

alkyl

procatalyst

carbon atoms

Prior art date

2013-12-20

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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• 239000003054 catalyst Substances 0.000 title claims abstract description 103
• 238000006116 polymerization reaction Methods 0.000 title claims abstract description 61
• 150000001336 alkenes Chemical class 0.000 title claims abstract description 43
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 32
• 238000000034 method Methods 0.000 claims abstract description 96
• 239000000203 mixture Substances 0.000 claims abstract description 77
• 239000012190 activator Substances 0.000 claims abstract description 47
• 229920000098 polyolefin Polymers 0.000 claims abstract description 43
• 230000008569 process Effects 0.000 claims abstract description 41
• 238000002360 preparation method Methods 0.000 claims abstract description 30
• 125000004432 carbon atom Chemical group C* 0.000 claims description 152
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 147
• -1 silyl diol esters Chemical class 0.000 claims description 139
• 150000001875 compounds Chemical class 0.000 claims description 118
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 239000011777 magnesium Substances 0.000 claims description 82
• 239000007787 solid Substances 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 71
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 66
• 239000007795 chemical reaction product Substances 0.000 claims description 54
• 125000005842 heteroatom Chemical group 0.000 claims description 52
• 229910052749 magnesium Inorganic materials 0.000 claims description 50
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 49
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 44
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 37
• 239000004743 Polypropylene Substances 0.000 claims description 35
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 125000004122 cyclic group Chemical group 0.000 claims description 33
• 229910052751 metal Inorganic materials 0.000 claims description 30
• 239000002184 metal Substances 0.000 claims description 30
• 229910052719 titanium Inorganic materials 0.000 claims description 30
• 230000003213 activating effect Effects 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• 229920001155 polypropylene Polymers 0.000 claims description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
• 229910052782 aluminium Inorganic materials 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 229910000077 silane Inorganic materials 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000005498 phthalate group Chemical class 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 229910052710 silicon Inorganic materials 0.000 claims description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical group NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 229910052735 hafnium Inorganic materials 0.000 claims description 11
• 229910052726 zirconium Inorganic materials 0.000 claims description 11
• 239000011954 Ziegler–Natta catalyst Substances 0.000 claims description 10
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
• VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 8
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 6
• 125000005059 halophenyl group Chemical group 0.000 claims description 6
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
• IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical group CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 claims description 5
• MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 5
• GNWGSBJQAXZWQZ-UHFFFAOYSA-N 4-[benzoyl(methyl)amino]pentan-2-yl benzoate Chemical group C=1C=CC=CC=1C(=O)OC(C)CC(C)N(C)C(=O)C1=CC=CC=C1 GNWGSBJQAXZWQZ-UHFFFAOYSA-N 0.000 claims description 4
• AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 claims description 4
• 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
• ZEELEKXGEHPYJR-UHFFFAOYSA-N 4-[benzoyl(ethyl)amino]pentan-2-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)N(CC)C(C)CC(C)OC(=O)C1=CC=CC=C1 ZEELEKXGEHPYJR-UHFFFAOYSA-N 0.000 claims description 3
• ZEKTUPBZSBAGKK-UHFFFAOYSA-N [3-[benzoyl(cyclohexyl)amino]-1-phenylbutyl] benzoate Chemical compound C1CCCCC1N(C(=O)C=1C=CC=CC=1)C(C)CC(C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 ZEKTUPBZSBAGKK-UHFFFAOYSA-N 0.000 claims description 3
• CBLPZPTZWXPRSI-UHFFFAOYSA-N [3-[benzoyl(propan-2-yl)amino]-1-phenylbutyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)N(C(C)C)C(C)CC(C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 CBLPZPTZWXPRSI-UHFFFAOYSA-N 0.000 claims description 3
• AZSPHNCRUVVMTI-UHFFFAOYSA-N [4-[benzoyl(methyl)amino]-1,1,1-trifluoropentan-2-yl] benzoate Chemical compound C=1C=CC=CC=1C(=O)N(C)C(C)CC(C(F)(F)F)OC(=O)C1=CC=CC=C1 AZSPHNCRUVVMTI-UHFFFAOYSA-N 0.000 claims description 3
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
• UUHWYBKYDFZQTQ-UHFFFAOYSA-N benzoic acid;2,2,6,6-tetramethyl-5-(methylamino)heptan-3-ol Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1.CNC(C(C)(C)C)CC(O)C(C)(C)C UUHWYBKYDFZQTQ-UHFFFAOYSA-N 0.000 claims description 3
• OMAQYRPCTCBANW-UHFFFAOYSA-N benzoic acid;2,2-dimethyl-3-(methylamino)propan-1-ol Chemical compound CNCC(C)(C)CO.OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 OMAQYRPCTCBANW-UHFFFAOYSA-N 0.000 claims description 3
• CQMMQEVQKPLQED-UHFFFAOYSA-N benzoic acid;3-(methylamino)-1,3-diphenylpropan-1-ol Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(NC)CC(O)C1=CC=CC=C1 CQMMQEVQKPLQED-UHFFFAOYSA-N 0.000 claims description 3
• FOVUUMLVUMGAEC-UHFFFAOYSA-N benzoic acid;3-(methylamino)propan-1-ol Chemical compound CNCCCO.OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 FOVUUMLVUMGAEC-UHFFFAOYSA-N 0.000 claims description 3
• CPDVHGLWIFENDJ-UHFFFAOYSA-N dihexylalumane Chemical compound C(CCCCC)[AlH]CCCCCC CPDVHGLWIFENDJ-UHFFFAOYSA-N 0.000 claims description 3
• ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 claims description 3
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 3
• LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 claims description 3
• LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 claims description 2
• QLLIVWGEMPGTMR-UHFFFAOYSA-N dihexyl(2-methylpropyl)alumane Chemical compound CCCCCC[Al](CC(C)C)CCCCCC QLLIVWGEMPGTMR-UHFFFAOYSA-N 0.000 claims description 2
• MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 claims description 2
• SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims description 2
• YGRHYJIWZFEDBT-UHFFFAOYSA-N tridecylaluminum Chemical compound CCCCCCCCCCCCC[Al] YGRHYJIWZFEDBT-UHFFFAOYSA-N 0.000 claims description 2
• XBEXIHMRFRFRAM-UHFFFAOYSA-N tridodecylalumane Chemical compound CCCCCCCCCCCC[Al](CCCCCCCCCCCC)CCCCCCCCCCCC XBEXIHMRFRFRAM-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 claims description 2
• 150000003890 succinate salts Chemical class 0.000 claims 2
• ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 claims 1
• OIPWQYPOWLBLMR-UHFFFAOYSA-N hexylalumane Chemical compound CCCCCC[AlH2] OIPWQYPOWLBLMR-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 abstract description 24
• 229940054066 benzamide antipsychotics Drugs 0.000 abstract description 8
• 150000003936 benzamides Chemical class 0.000 abstract description 8
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 50
• 229920000642 polymer Polymers 0.000 description 47
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
• 239000010936 titanium Substances 0.000 description 40
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 38
• 239000002904 solvent Substances 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 35
• 229910052723 transition metal Inorganic materials 0.000 description 32
• 150000003624 transition metals Chemical class 0.000 description 32
• 241000894007 species Species 0.000 description 31
• 238000002156 mixing Methods 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 28
• 239000000243 solution Substances 0.000 description 28
• 230000003197 catalytic effect Effects 0.000 description 27
• 239000002245 particle Substances 0.000 description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 239000003607 modifier Substances 0.000 description 24
• 238000003756 stirring Methods 0.000 description 24
• 238000009826 distribution Methods 0.000 description 23
• 150000004820 halides Chemical class 0.000 description 23
• 239000013067 intermediate product Substances 0.000 description 22
• 239000000047 product Substances 0.000 description 19
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
• 239000005977 Ethylene Substances 0.000 description 16
• 239000002270 dispersing agent Substances 0.000 description 16
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
• 239000012071 phase Substances 0.000 description 16
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 16
• 230000004913 activation Effects 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• 239000011343 solid material Substances 0.000 description 15
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
• 229920001577 copolymer Polymers 0.000 description 14
• DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 14
• 239000007789 gas Substances 0.000 description 14
• 238000010908 decantation Methods 0.000 description 13
• 230000000737 periodic effect Effects 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 12
• 150000004703 alkoxides Chemical class 0.000 description 12
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 229910021482 group 13 metal Inorganic materials 0.000 description 11
• 239000000178 monomer 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
• 239000000376 reactant Substances 0.000 description 11
• 229920001169 thermoplastic Polymers 0.000 description 11
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 229910052804 chromium Inorganic materials 0.000 description 10
• 239000011651 chromium Substances 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
• 239000006228 supernatant Substances 0.000 description 10
• 229910052720 vanadium Inorganic materials 0.000 description 10
• 239000008096 xylene Substances 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 9
• 125000003545 alkoxy group Chemical group 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 230000001965 increasing effect Effects 0.000 description 9
• 239000002002 slurry Substances 0.000 description 9
• HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 8
• 238000002474 experimental method Methods 0.000 description 8
• ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
• 239000000654 additive Substances 0.000 description 7
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 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 7
• 229910052740 iodine Inorganic materials 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 150000003900 succinic acid esters Chemical class 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 238000012685 gas phase polymerization Methods 0.000 description 6
• QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 6
• 230000004048 modification Effects 0.000 description 6
• 238000012986 modification Methods 0.000 description 6
• 229910052698 phosphorus Inorganic materials 0.000 description 6
• 230000035484 reaction time Effects 0.000 description 6
• 239000000377 silicon dioxide Substances 0.000 description 6
• 239000011949 solid catalyst Substances 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 6
• 238000005406 washing Methods 0.000 description 6
• ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• 229940064734 aminobenzoate Drugs 0.000 description 5
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 230000008901 benefit Effects 0.000 description 5
• 150000001735 carboxylic acids Chemical class 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 5
• VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 5
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• DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
• CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
• BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-UHFFFAOYSA-N 0.000 description 1
• QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
• JNLSTWIBJFIVHZ-UHFFFAOYSA-K trifluoroindigane Chemical compound F[In](F)F JNLSTWIBJFIVHZ-UHFFFAOYSA-K 0.000 description 1
• RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 0.000 description 1
• SFRFZGGTKJZREP-UHFFFAOYSA-K triiodothallane Chemical compound [I-].[I-].[I-].[Tl+3] SFRFZGGTKJZREP-UHFFFAOYSA-K 0.000 description 1
• AAWFOGYSSVYINI-UHFFFAOYSA-K triiodovanadium Chemical compound I[V](I)I AAWFOGYSSVYINI-UHFFFAOYSA-K 0.000 description 1
• LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
• VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
• ZOYIPGHJSALYPY-UHFFFAOYSA-K vanadium(iii) bromide Chemical compound [V+3].[Br-].[Br-].[Br-] ZOYIPGHJSALYPY-UHFFFAOYSA-K 0.000 description 1
• HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1
• UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 1