DE19962910A1

DE19962910A1 - Chemische Verbindung, Verfahren zu deren Herstellung und deren Verwendung in Katalysatorsystemen zur Herstellung von Polyolefinen

Chemische Verbindung, Verfahren zu deren Herstellung und deren Verwendung in Katalysatorsystemen zur Herstellung von Polyolefinen

Info

Publication number: DE19962910A1
Authority: DE; Germany
Prior art keywords: methyl; borate; indenyl; zirconium dichloride; tetrakis
Prior art date: 1999-12-23
Legal status : Withdrawn

Application number

DE19962910A

Other languages

German (de)

English (en)

Inventor

Joerg Schottek

Iris Kuellmer

Heike Gregorius

David Fischer

Current Assignee

Basell Polyolefine GmbH

Original Assignee

Targor GmbH

Priority date

1999-12-23

Filing date

1999-12-23

Publication date

2001-07-05

1999-12-23 Application filed by Targor GmbH filed Critical Targor GmbH

1999-12-23 Priority to DE19962910A priority Critical patent/DE19962910A1/de

2000-12-21 Priority to AT00991248T priority patent/ATE338075T1/de

2000-12-21 Priority to EP00991248A priority patent/EP1250363B1/de

2000-12-21 Priority to PCT/EP2000/013096 priority patent/WO2001048035A2/de

2000-12-21 Priority to JP2001548573A priority patent/JP2003518516A/ja

2000-12-21 Priority to DE50013407T priority patent/DE50013407D1/de

2000-12-21 Priority to US10/168,719 priority patent/US7101940B2/en

2001-07-05 Publication of DE19962910A1 publication Critical patent/DE19962910A1/de

Status Withdrawn legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 48
239000003054 catalyst Substances 0.000 title claims description 46
238000000034 method Methods 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title claims description 8
229920000098 polyolefin Polymers 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 5
125000004122 cyclic group Chemical group 0.000 claims abstract description 25
229910052799 carbon Inorganic materials 0.000 claims abstract description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
230000000737 periodic effect Effects 0.000 claims abstract description 13
150000001768 cations Chemical class 0.000 claims abstract description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 332
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 116
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 106
LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 67
229910052757 nitrogen Inorganic materials 0.000 claims description 61
CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 claims description 37
238000006116 polymerization reaction Methods 0.000 claims description 25
150000001336 alkenes Chemical class 0.000 claims description 24
125000003710 aryl alkyl group Chemical group 0.000 claims description 23
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 22
125000003106 haloaryl group Chemical group 0.000 claims description 19
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 14
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 14
125000002877 alkyl aryl group Chemical group 0.000 claims description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 13
125000004104 aryloxy group Chemical group 0.000 claims description 12
125000006492 halo alkyl aryl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000002034 haloarylalkyl group Chemical group 0.000 claims description 9
229920000642 polymer Polymers 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 claims description 8
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
229910052782 aluminium Inorganic materials 0.000 claims description 6
229910052796 boron Inorganic materials 0.000 claims description 6
230000007704 transition Effects 0.000 claims description 6
125000002524 organometallic group Chemical group 0.000 claims description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 claims description 4
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 4
239000002879 Lewis base Substances 0.000 claims description 3
150000007527 lewis bases Chemical class 0.000 claims description 3
UWHRNIXHZAWBMF-UHFFFAOYSA-N n-dodecyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCCCCCCCCCCC UWHRNIXHZAWBMF-UHFFFAOYSA-N 0.000 claims description 3
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 claims description 2
OCZBPNBIXHLBFM-UHFFFAOYSA-N n,n-di(propan-2-yl)cyclohexanamine Chemical compound CC(C)N(C(C)C)C1CCCCC1 OCZBPNBIXHLBFM-UHFFFAOYSA-N 0.000 claims description 2
IQSLPSKHVSSQOH-UHFFFAOYSA-N n,n-dibutyldecan-1-amine Chemical compound CCCCCCCCCCN(CCCC)CCCC IQSLPSKHVSSQOH-UHFFFAOYSA-N 0.000 claims description 2
FPFTUTDQPYXFSM-UHFFFAOYSA-N n,n-didodecylcyclohexanamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)C1CCCCC1 FPFTUTDQPYXFSM-UHFFFAOYSA-N 0.000 claims description 2
YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 claims description 2
NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 claims description 2
CWAIAZCEPCBUON-UHFFFAOYSA-N n-icosyl-n-methylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCCCC CWAIAZCEPCBUON-UHFFFAOYSA-N 0.000 claims description 2
VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 claims description 2
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 claims description 2
NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 claims 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
NNMCLUGKHHLNKX-UHFFFAOYSA-N n,n-didecyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCC)CCCCCCCCCC NNMCLUGKHHLNKX-UHFFFAOYSA-N 0.000 claims 1
XJIXQZHZNXTYRV-UHFFFAOYSA-N n,n-didecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCC)CCCCCCCCCC XJIXQZHZNXTYRV-UHFFFAOYSA-N 0.000 claims 1
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims 1
GOTQULLXGZGQMK-UHFFFAOYSA-N n-benzyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CC1=CC=CC=C1 GOTQULLXGZGQMK-UHFFFAOYSA-N 0.000 claims 1
KCMTVIZYKDBFFS-UHFFFAOYSA-N n-hexadecyl-n-methylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCC KCMTVIZYKDBFFS-UHFFFAOYSA-N 0.000 claims 1
KUFYUMSBZMUWAN-UHFFFAOYSA-N n-methyl-n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCC KUFYUMSBZMUWAN-UHFFFAOYSA-N 0.000 claims 1
-1 perfluorinated tetraphenylborates Chemical class 0.000 description 416
VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 88
150000001412 amines Chemical class 0.000 description 63
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 21
229910052744 lithium Inorganic materials 0.000 description 21
239000007983 Tris buffer Substances 0.000 description 20
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 19
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 18
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 18
229910052700 potassium Inorganic materials 0.000 description 18
239000011591 potassium Substances 0.000 description 18
229910052708 sodium Inorganic materials 0.000 description 18
239000011734 sodium Substances 0.000 description 18
229910052726 zirconium Inorganic materials 0.000 description 16
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000012876 carrier material Substances 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 11
239000007789 gas Substances 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
238000003786 synthesis reaction Methods 0.000 description 9
DDXMXHFSQQUJFF-UHFFFAOYSA-N (2,3,4,6-tetrafluoro-5-methoxyphenoxy)boronic acid Chemical compound COC1=C(F)C(F)=C(F)C(OB(O)O)=C1F DDXMXHFSQQUJFF-UHFFFAOYSA-N 0.000 description 8
BWOONEDTGJUENF-UHFFFAOYSA-N (2,3,4,6-tetrafluoro-5-methylphenoxy)boronic acid Chemical compound CC1=C(F)C(F)=C(F)C(OB(O)O)=C1F BWOONEDTGJUENF-UHFFFAOYSA-N 0.000 description 8
PKNXWXIOHMVSPA-UHFFFAOYSA-N (2,4,6-trifluoro-3-methylphenoxy)boronic acid Chemical compound CC1=C(F)C=C(F)C(OB(O)O)=C1F PKNXWXIOHMVSPA-UHFFFAOYSA-N 0.000 description 8
MMWDAJAFHLFILV-UHFFFAOYSA-N (2,6-difluoro-3-methylphenoxy)boronic acid Chemical compound CC1=CC=C(F)C(OB(O)O)=C1F MMWDAJAFHLFILV-UHFFFAOYSA-N 0.000 description 8
IFKYPHHIFNSPNK-UHFFFAOYSA-N (3,4,6-trifluoro-2-methylphenoxy)boronic acid Chemical compound CC1=C(F)C(F)=CC(F)=C1OB(O)O IFKYPHHIFNSPNK-UHFFFAOYSA-N 0.000 description 8
SVTYWVXZGDAWDG-UHFFFAOYSA-N (3,5-difluoro-2-methylphenoxy)boronic acid Chemical compound CC1=C(F)C=C(F)C=C1OB(O)O SVTYWVXZGDAWDG-UHFFFAOYSA-N 0.000 description 8
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
XBBVGTDZNACBIW-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methoxyphenoxy)boronic acid Chemical compound COC1=C(F)C(F)=C(OB(O)O)C(F)=C1F XBBVGTDZNACBIW-UHFFFAOYSA-N 0.000 description 7
XQSHNVWECPGIGB-UHFFFAOYSA-N (2,3,6-trifluoro-4-methylphenoxy)boronic acid Chemical compound CC1=CC(F)=C(OB(O)O)C(F)=C1F XQSHNVWECPGIGB-UHFFFAOYSA-N 0.000 description 7
XXMNSSKYPKSJOH-UHFFFAOYSA-L C[Si](=CC1=CC2=CC=NC2=C1)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC1=CC2=CC=NC2=C1)C.[Cl-].[Cl-].[Zr+2] XXMNSSKYPKSJOH-UHFFFAOYSA-L 0.000 description 7
LJDLJFKCGOQWLH-UHFFFAOYSA-L C[Si](=CC1=CC2=CCSC2=C1)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC1=CC2=CCSC2=C1)C.[Cl-].[Cl-].[Zr+2] LJDLJFKCGOQWLH-UHFFFAOYSA-L 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
229910052786 argon Inorganic materials 0.000 description 7
238000001035 drying Methods 0.000 description 7
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
239000003446 ligand Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
TZEQJYRYMIBGAM-UHFFFAOYSA-N (2,3,4,5-tetrafluoro-6-methoxyphenoxy)boronic acid Chemical compound COC1=C(F)C(F)=C(F)C(F)=C1OB(O)O TZEQJYRYMIBGAM-UHFFFAOYSA-N 0.000 description 6
JXTPPJGAAFJFMR-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methylphenoxy)boronic acid Chemical compound CC1=C(F)C(F)=C(OB(O)O)C(F)=C1F JXTPPJGAAFJFMR-UHFFFAOYSA-N 0.000 description 6
CZWAQIALFQKSKD-UHFFFAOYSA-N (2,3,5-trifluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC(F)=CC(F)=C1F CZWAQIALFQKSKD-UHFFFAOYSA-N 0.000 description 6
HLVPGBSZESESKG-UHFFFAOYSA-N (2,4-difluoro-5-methylphenoxy)boronic acid Chemical compound CC1=CC(OB(O)O)=C(F)C=C1F HLVPGBSZESESKG-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
GCPYSPSXOKVXOK-UHFFFAOYSA-L C[Si](=CC1C=C2C=C(C=C2O1)C)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC1C=C2C=C(C=C2O1)C)C.[Cl-].[Cl-].[Zr+2] GCPYSPSXOKVXOK-UHFFFAOYSA-L 0.000 description 6
FLJDLWIESSEPCG-UHFFFAOYSA-L C[Si](=CC1C=C2C=C(C=C2S1)C)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC1C=C2C=C(C=C2S1)C)C.[Cl-].[Cl-].[Zr+2] FLJDLWIESSEPCG-UHFFFAOYSA-L 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000004913 activation Effects 0.000 description 6
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 6
238000006297 dehydration reaction Methods 0.000 description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
GKPQATDUBIVTSI-UHFFFAOYSA-L C[Si](=CC1=CC2=CSCC2=C1)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC1=CC2=CSCC2=C1)C.[Cl-].[Cl-].[Zr+2] GKPQATDUBIVTSI-UHFFFAOYSA-L 0.000 description 5
MZQPVBRTTLTWGW-UHFFFAOYSA-L C[Si](=CC=1C=C2OCC=C2C1)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC=1C=C2OCC=C2C1)C.[Cl-].[Cl-].[Zr+2] MZQPVBRTTLTWGW-UHFFFAOYSA-L 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
150000002736 metal compounds Chemical class 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
WFMWNJXHNPVTMO-UHFFFAOYSA-N (2,3,6-trifluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C=CC(F)=C1F WFMWNJXHNPVTMO-UHFFFAOYSA-N 0.000 description 4
DZETZMSAJDMAKS-UHFFFAOYSA-L Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 DZETZMSAJDMAKS-UHFFFAOYSA-L 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000002216 antistatic agent Substances 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
150000001642 boronic acid derivatives Chemical class 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
229920001155 polypropylene Polymers 0.000 description 4
239000011148 porous material Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000004044 response Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 4
RURFJXKOXIWFJX-UHFFFAOYSA-N (2,3,4,6-tetrafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C=C(F)C(F)=C1F RURFJXKOXIWFJX-UHFFFAOYSA-N 0.000 description 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
238000004293 19F NMR spectroscopy Methods 0.000 description 3
SFJZQGYBQXBYDT-UHFFFAOYSA-L C[Si](=CC1=CC2=CN=CC2=C1)C.[Cl-].[Cl-].[Zr+2] Chemical compound C[Si](=CC1=CC2=CN=CC2=C1)C.[Cl-].[Cl-].[Zr+2] SFJZQGYBQXBYDT-UHFFFAOYSA-L 0.000 description 3
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238000005481 NMR spectroscopy Methods 0.000 description 3
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150000003624 transition metals Chemical group 0.000 description 3
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