KR100635413B1 - 메탈로센 모노할로게나이드 - Google Patents

Info

Publication number

KR100635413B1

KR100635413B1 KR1020007007880A KR20007007880A KR100635413B1 KR 100635413 B1 KR100635413 B1 KR 100635413B1 KR 1020007007880 A KR1020007007880 A KR 1020007007880A KR 20007007880 A KR20007007880 A KR 20007007880A KR 100635413 B1 KR100635413 B1 KR 100635413B1

Authority

KR

South Korea

Prior art keywords

butylphenoxide

zirconium monochloride

monochloride mono

fluorinated

dimethylsilanediylbis

Prior art date

1998-11-25

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.)

Expired - Lifetime

Links

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• -1 C 1 -C 18 -alkyl Chemical group 0.000 claims description 126
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical class [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 53
• 239000003054 catalyst Substances 0.000 claims description 45
• 150000001875 compounds Chemical class 0.000 claims description 31
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 229910052726 zirconium Inorganic materials 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 8
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
• 229920000098 polyolefin Polymers 0.000 claims description 7
• QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 238000004132 cross linking Methods 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 229910052735 hafnium Inorganic materials 0.000 claims description 5
• 229910052717 sulfur Chemical group 0.000 claims description 5
• 239000011593 sulfur Chemical group 0.000 claims description 5
• 229910052719 titanium Inorganic materials 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
• 125000003367 polycyclic group Chemical group 0.000 claims 1
• 238000006116 polymerization reaction Methods 0.000 abstract description 24
• 150000001336 alkenes Chemical class 0.000 abstract description 15
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 125
• NKXHUIPTBRWUOI-UHFFFAOYSA-L 2,4-ditert-butylphenolate;zirconium(2+);chloride Chemical compound [Cl-].[Zr+2].CC(C)(C)C1=CC=C([O-])C(C(C)(C)C)=C1 NKXHUIPTBRWUOI-UHFFFAOYSA-L 0.000 description 93
• 239000002904 solvent Substances 0.000 description 37
• 239000000203 mixture Substances 0.000 description 32
• 239000000243 solution Substances 0.000 description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 239000000463 material Substances 0.000 description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
• 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 description 16
• 238000000034 method Methods 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 14
• 150000003254 radicals Chemical class 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 239000004743 Polypropylene Substances 0.000 description 10
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
• 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 10
• 238000002360 preparation method Methods 0.000 description 10
• 238000001035 drying Methods 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 229930195733 hydrocarbon Natural products 0.000 description 9
• OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 9
• 229920000642 polymer Polymers 0.000 description 9
• 229920001155 polypropylene Polymers 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 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 description 8
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
• CIYCKVXGRWSAQQ-UHFFFAOYSA-M [Cl-].[Zr+] Chemical compound [Cl-].[Zr+] CIYCKVXGRWSAQQ-UHFFFAOYSA-M 0.000 description 8
• 239000011148 porous material Substances 0.000 description 8
• 229910052710 silicon Inorganic materials 0.000 description 8
• IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 8
• VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 8
• YARHKKPNVOLRNL-UHFFFAOYSA-N 2,4-ditert-butylphenol hydrochloride Chemical compound Cl.CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 YARHKKPNVOLRNL-UHFFFAOYSA-N 0.000 description 7
• 229920001577 copolymer Polymers 0.000 description 7
• 125000002541 furyl group Chemical group 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• 125000004076 pyridyl group Chemical group 0.000 description 7
• 125000005493 quinolyl group Chemical group 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 238000005160 1H NMR spectroscopy Methods 0.000 description 6
• ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• ZJUUJFBRTBZESG-UHFFFAOYSA-L C(C)(C)(C)C1=C([O-])C=CC(=C1)C(C)(C)C.[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C Chemical compound C(C)(C)(C)C1=C([O-])C=CC(=C1)C(C)(C)C.[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C ZJUUJFBRTBZESG-UHFFFAOYSA-L 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 238000006297 dehydration reaction Methods 0.000 description 6
• 238000001704 evaporation Methods 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
• MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 6
• IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 6
• HDMOFROBWDTHCS-UHFFFAOYSA-L C(C)(C)C1=C([O-])C=C(C=C1)C.[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C Chemical compound C(C)(C)C1=C([O-])C=C(C=C1)C.[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C HDMOFROBWDTHCS-UHFFFAOYSA-L 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• CGELJBSWQTYCIY-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2ccccc2[C@H]1[Zr++]([C@@H]1C(C)=Cc2ccccc12)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=Cc2ccccc2[C@H]1[Zr++]([C@@H]1C(C)=Cc2ccccc12)=[Si](C)C CGELJBSWQTYCIY-UHFFFAOYSA-L 0.000 description 5
• 230000004913 activation Effects 0.000 description 5
• 150000004645 aluminates Chemical class 0.000 description 5
• 230000008020 evaporation Effects 0.000 description 5
• 150000002430 hydrocarbons Chemical class 0.000 description 5
• 239000001257 hydrogen Substances 0.000 description 5
• 229910052739 hydrogen Inorganic materials 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• 239000000178 monomer Substances 0.000 description 5
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 5
• 230000000737 periodic effect Effects 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• CFNFUAFGGQRYEN-UHFFFAOYSA-N 2-cyclopenta[b]pyrrol-2-ylethylidene(dimethyl)silane Chemical compound C[Si](=CCC1=NC2=CC=CC2=C1)C CFNFUAFGGQRYEN-UHFFFAOYSA-N 0.000 description 4
• GURBASLETYFBHY-UHFFFAOYSA-N 5-methyl-2-propan-2-ylphenol;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(C)C=C1O GURBASLETYFBHY-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
• QRQHAUFMHIZSHV-UHFFFAOYSA-L CC1=C([O-])C=CC(=C1)C.[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C Chemical compound CC1=C([O-])C=CC(=C1)C.[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C QRQHAUFMHIZSHV-UHFFFAOYSA-L 0.000 description 4
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 229910052782 aluminium Inorganic materials 0.000 description 4
• 239000002216 antistatic agent Substances 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• FUBWDZHVOMHPJC-UHFFFAOYSA-N cyclopenta[b]pyrrol-2-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=NC2=CC=CC2=C1)C FUBWDZHVOMHPJC-UHFFFAOYSA-N 0.000 description 4
• 230000018044 dehydration Effects 0.000 description 4
• JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 239000012442 inert solvent Substances 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 239000002245 particle Substances 0.000 description 4
• 239000010703 silicon Substances 0.000 description 4
• 125000003944 tolyl group Chemical group 0.000 description 4
• 229910052723 transition metal Inorganic materials 0.000 description 4
• 150000003624 transition metals Chemical class 0.000 description 4
• HAKXWBMWJFMXJZ-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol hydrochloride Chemical compound Cl.CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 HAKXWBMWJFMXJZ-UHFFFAOYSA-N 0.000 description 3
• GCWHBFHMFFWSSK-UHFFFAOYSA-N 2-(2H-cyclopenta[b]thiophen-2-yl)ethylidene-dimethylsilane Chemical compound C[Si](=CCC1SC2=CC=CC2=C1)C GCWHBFHMFFWSSK-UHFFFAOYSA-N 0.000 description 3
• CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 3
• HGZUHRHKSFYMEH-UHFFFAOYSA-N 2H-cyclopenta[b]thiophen-2-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1SC2=CC=CC2=C1)C HGZUHRHKSFYMEH-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 239000002841 Lewis acid Substances 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 125000002091 cationic group Chemical group 0.000 description 3
• 150000001768 cations Chemical class 0.000 description 3
• 238000007334 copolymerization reaction Methods 0.000 description 3
• 238000002425 crystallisation Methods 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 150000004820 halides Chemical class 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 229910052809 inorganic oxide Inorganic materials 0.000 description 3
• 150000008040 ionic compounds Chemical class 0.000 description 3
• 150000007517 lewis acids Chemical class 0.000 description 3
• 229910052757 nitrogen Inorganic materials 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 239000000376 reactant Substances 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 239000013557 residual solvent Substances 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• 239000011877 solvent mixture Substances 0.000 description 3
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
• 239000010936 titanium Substances 0.000 description 3
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
• OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• HTGQCLJTWPSFNL-UHFFFAOYSA-N (2-methylphenoxy)boronic acid Chemical compound CC1=CC=CC=C1OB(O)O HTGQCLJTWPSFNL-UHFFFAOYSA-N 0.000 description 2
• XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
• PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 2
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
• KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
• OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
• KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
• PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
• WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 2
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• LKNHGIFPRLUGEG-UHFFFAOYSA-N tris(3,4,5-trifluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C=C(F)C(F)=C(F)C=2)C=2C=C(F)C(F)=C(F)C=2)=C1 LKNHGIFPRLUGEG-UHFFFAOYSA-N 0.000 description 1
• OHSAEOPCBBOWPU-UHFFFAOYSA-N tris(3,5-dimethylphenyl)borane Chemical compound CC1=CC(C)=CC(B(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 OHSAEOPCBBOWPU-UHFFFAOYSA-N 0.000 description 1
• YPVVTWIAXFPZLS-UHFFFAOYSA-N tris(4-fluorophenyl)borane Chemical compound C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 YPVVTWIAXFPZLS-UHFFFAOYSA-N 0.000 description 1
• OSMBUUFIZBTSNO-UHFFFAOYSA-N tris[4-(fluoromethyl)phenyl]borane Chemical compound C1=CC(CF)=CC=C1B(C=1C=CC(CF)=CC=1)C1=CC=C(CF)C=C1 OSMBUUFIZBTSNO-UHFFFAOYSA-N 0.000 description 1
• 150000003672 ureas 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
• 125000005023 xylyl group Chemical group 0.000 description 1
• RRKNTBCIGSOMTH-UHFFFAOYSA-L zirconium(2+);chloride;phenoxide Chemical compound [Cl-].[Zr+2].[O-]C1=CC=CC=C1 RRKNTBCIGSOMTH-UHFFFAOYSA-L 0.000 description 1
• 239000004711 α-olefin Substances 0.000 description 1