JP3907475B2 - 不飽和化合物の重合用触媒 - Google Patents
不飽和化合物の重合用触媒 Download PDFInfo
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- JP3907475B2 JP3907475B2 JP2001518721A JP2001518721A JP3907475B2 JP 3907475 B2 JP3907475 B2 JP 3907475B2 JP 2001518721 A JP2001518721 A JP 2001518721A JP 2001518721 A JP2001518721 A JP 2001518721A JP 3907475 B2 JP3907475 B2 JP 3907475B2
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- ylimine
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 95
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 52
- 239000003054 catalyst Substances 0.000 title claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 125000003118 aryl group Chemical group 0.000 claims abstract description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 229910052755 nonmetal Inorganic materials 0.000 claims abstract description 8
- BEZVGIHGZPLGBL-UHFFFAOYSA-N 2,6-diacetylpyridine Chemical compound CC(=O)C1=CC=CC(C(C)=O)=N1 BEZVGIHGZPLGBL-UHFFFAOYSA-N 0.000 claims description 35
- -1 2,6-diacetylpyridine bis (2,3,5-triphenylpyrrol-1-ylimine) Chemical compound 0.000 claims description 34
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
- 239000005977 Ethylene Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 230000000737 periodic effect Effects 0.000 claims description 9
- 239000012190 activator Substances 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- NPKFPVNRIFGCNQ-UHFFFAOYSA-N 1-[6-[c-methyl-n-[2-methyl-5-(2-methylphenyl)pyrrol-1-yl]carbonimidoyl]pyridin-2-yl]-n-[2-methyl-5-(2-methylphenyl)pyrrol-1-yl]ethanimine Chemical compound C=1C=CC(C(C)=NN2C(=CC=C2C)C=2C(=CC=CC=2)C)=NC=1C(C)=NN1C(C)=CC=C1C1=CC=CC=C1C NPKFPVNRIFGCNQ-UHFFFAOYSA-N 0.000 claims description 7
- KLXJPGNFLJUXDM-UHFFFAOYSA-N N-(2-methylindol-1-yl)-1-[6-[C-methyl-N-(2-methylindol-1-yl)carbonimidoyl]pyridin-2-yl]ethanimine Chemical compound CC=1N(C2=CC=CC=C2C=1)N=C(C)C1=CC=CC(=N1)C(C)=NN1C(=CC2=CC=CC=C12)C KLXJPGNFLJUXDM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 150000001925 cycloalkenes Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- UGXGQSXMWZUKGS-UHFFFAOYSA-N N-(3,5-dimethyl-1,2,4-triazol-4-yl)-1-[6-[N-(3,5-dimethyl-1,2,4-triazol-4-yl)-C-methylcarbonimidoyl]pyridin-2-yl]ethanimine Chemical compound CC1=NN=C(N1N=C(C)C1=CC=CC(=N1)C(C)=NN1C(=NN=C1C)C)C UGXGQSXMWZUKGS-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 229940117927 ethylene oxide Drugs 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 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
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000005673 monoalkenes Chemical class 0.000 claims description 2
- 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 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000012456 homogeneous solution Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 20
- 239000003446 ligand Substances 0.000 description 20
- 230000008018 melting Effects 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- 230000005298 paramagnetic effect Effects 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 17
- 238000001914 filtration Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- YNZAFFFENDLJQG-UHFFFAOYSA-N pyrrol-1-amine Chemical compound NN1C=CC=C1 YNZAFFFENDLJQG-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- IDHCQGUWHXGMQW-UHFFFAOYSA-N 1-(2-acetylpyridin-3-yl)ethanone Chemical compound CC(=O)C1=CC=CN=C1C(C)=O IDHCQGUWHXGMQW-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Chemical group 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 229910000071 diazene Inorganic materials 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- LPDMGHFMHRQJHA-UHFFFAOYSA-N n-[2,5-di(propan-2-yl)pyrrol-1-yl]-1-[6-[n-[2,5-di(propan-2-yl)pyrrol-1-yl]-c-methylcarbonimidoyl]pyridin-2-yl]ethanimine Chemical compound CC(C)C1=CC=C(C(C)C)N1N=C(C)C1=CC=CC(C(C)=NN2C(=CC=C2C(C)C)C(C)C)=N1 LPDMGHFMHRQJHA-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 7
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 6
- VXIKDBJPBRMXBP-UHFFFAOYSA-N 3H-pyrrole Chemical compound C1C=CN=C1 VXIKDBJPBRMXBP-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000010414 supernatant solution Substances 0.000 description 5
- UTJHNEXXLCCFDC-UHFFFAOYSA-N 2,3,5-triphenylpyrrol-1-amine Chemical compound NN1C(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 UTJHNEXXLCCFDC-UHFFFAOYSA-N 0.000 description 4
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 150000008040 ionic compounds Chemical class 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JFRCYWLQPGRDIO-UHFFFAOYSA-N 2-methyl-5-(2-methylphenyl)pyrrol-1-amine Chemical compound NN1C(C)=CC=C1C1=CC=CC=C1C JFRCYWLQPGRDIO-UHFFFAOYSA-N 0.000 description 3
- AFNRQIJNLQADSI-UHFFFAOYSA-N 2-methyl-5-phenylpyrrol-1-amine Chemical compound NN1C(C)=CC=C1C1=CC=CC=C1 AFNRQIJNLQADSI-UHFFFAOYSA-N 0.000 description 3
- PCCGESRTELLLGU-UHFFFAOYSA-N 2-methyl-5-propan-2-ylpyrrol-1-amine Chemical compound CC(C)C1=CC=C(C)N1N PCCGESRTELLLGU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000003106 haloaryl group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- FXFQHHIBUWXNGL-UHFFFAOYSA-N n-(2,3,5-triphenylpyrrol-1-yl)acetamide Chemical compound CC(=O)NN1C(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FXFQHHIBUWXNGL-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XRDLHHMCBNGYRQ-UHFFFAOYSA-N 1-(2-methylphenyl)pentane-1,4-dione Chemical compound CC(=O)CCC(=O)C1=CC=CC=C1C XRDLHHMCBNGYRQ-UHFFFAOYSA-N 0.000 description 2
- ZCFLWHJMPGUOJC-UHFFFAOYSA-N 1-[6-[C-methyl-N-(2-methyl-5-propan-2-ylpyrrol-1-yl)carbonimidoyl]pyridin-2-yl]-N-(2-methyl-5-propan-2-ylpyrrol-1-yl)ethanimine Chemical compound CC=1N(C(=CC=1)C(C)C)N=C(C)C1=CC=CC(=N1)C(C)=NN1C(=CC=C1C(C)C)C ZCFLWHJMPGUOJC-UHFFFAOYSA-N 0.000 description 2
- IRUXKWDBGDAKKV-UHFFFAOYSA-N 1-[6-[c-methyl-n-(2-methyl-5-phenylpyrrol-1-yl)carbonimidoyl]pyridin-2-yl]-n-(2-methyl-5-phenylpyrrol-1-yl)ethanimine Chemical compound C=1C=CC(C(C)=NN2C(=CC=C2C)C=2C=CC=CC=2)=NC=1C(C)=NN1C(C)=CC=C1C1=CC=CC=C1 IRUXKWDBGDAKKV-UHFFFAOYSA-N 0.000 description 2
- QVFIRPJGSQGVKH-UHFFFAOYSA-N 2,5-di(propan-2-yl)pyrrol-1-amine Chemical compound CC(C)C1=CC=C(C(C)C)N1N QVFIRPJGSQGVKH-UHFFFAOYSA-N 0.000 description 2
- QXGIEALBOGPCMJ-UHFFFAOYSA-N 2,5-diphenylpyrrol-1-amine Chemical compound NN1C(C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 QXGIEALBOGPCMJ-UHFFFAOYSA-N 0.000 description 2
- ZVEGQLNQUKGLNF-UHFFFAOYSA-N 2-methylindol-1-amine Chemical compound C1=CC=C2N(N)C(C)=CC2=C1 ZVEGQLNQUKGLNF-UHFFFAOYSA-N 0.000 description 2
- MIIKMZAVLKMOFM-UHFFFAOYSA-N 3,5-dimethyl-1,2,4-triazol-4-amine Chemical compound CC1=NN=C(C)N1N MIIKMZAVLKMOFM-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021581 Cobalt(III) chloride Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 2
- DEXRWZJZHXRZDO-UHFFFAOYSA-N N-(2,5-diphenylpyrrol-1-yl)-1-[6-[N-(2,5-diphenylpyrrol-1-yl)-C-methylcarbonimidoyl]pyridin-2-yl]ethanimine Chemical compound C=1C=CC(C(C)=NN2C(=CC=C2C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C(C)=NN1C(C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 DEXRWZJZHXRZDO-UHFFFAOYSA-N 0.000 description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
- 229910002666 PdCl2 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- CGTWOOPTAAXMLM-UHFFFAOYSA-N carbazol-9-amine Chemical compound C1=CC=C2N(N)C3=CC=CC=C3C2=C1 CGTWOOPTAAXMLM-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- 239000001282 iso-butane Substances 0.000 description 2
- 239000011565 manganese chloride Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
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- QJMWWIOKKPJMGR-UHFFFAOYSA-N n-(2,5-dimethylpyrrol-1-yl)-1-[6-[n-(2,5-dimethylpyrrol-1-yl)-c-methylcarbonimidoyl]pyridin-2-yl]ethanimine Chemical compound C=1C=CC(C(C)=NN2C(=CC=C2C)C)=NC=1C(C)=NN1C(C)=CC=C1C QJMWWIOKKPJMGR-UHFFFAOYSA-N 0.000 description 2
- DBQUJQVGZRTRNV-UHFFFAOYSA-N n-(2-methyl-5-phenylpyrrol-1-yl)acetamide Chemical compound CC(=O)NN1C(C)=CC=C1C1=CC=CC=C1 DBQUJQVGZRTRNV-UHFFFAOYSA-N 0.000 description 2
- JEDBXPMFUJWTPS-UHFFFAOYSA-N n-(2-methyl-5-propan-2-ylpyrrol-1-yl)acetamide Chemical compound CC(C)C1=CC=C(C)N1NC(C)=O JEDBXPMFUJWTPS-UHFFFAOYSA-N 0.000 description 2
- KKOUTCABOHEIFQ-UHFFFAOYSA-N n-[2-methyl-5-(2-methylphenyl)pyrrol-1-yl]acetamide Chemical compound CC(=O)NN1C(C)=CC=C1C1=CC=CC=C1C KKOUTCABOHEIFQ-UHFFFAOYSA-N 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- OTMRXENQDSQACG-UHFFFAOYSA-N thiophene-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)S1 OTMRXENQDSQACG-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- PVEUVUMVYFGUGB-UHFFFAOYSA-N 2,5-di(propan-2-yl)-1h-pyrrole Chemical compound CC(C)C1=CC=C(C(C)C)N1 PVEUVUMVYFGUGB-UHFFFAOYSA-N 0.000 description 1
- BDQRQMLWZJQQKS-UHFFFAOYSA-M 2-(3-ethyl-4-methyl-1,3-thiazol-3-ium-5-yl)ethanol;bromide Chemical compound [Br-].CC[N+]1=CSC(CCO)=C1C BDQRQMLWZJQQKS-UHFFFAOYSA-M 0.000 description 1
- VYYVHHWQRAEFOL-UHFFFAOYSA-N 4-[(4-aminophenoxy)methyl]aniline Chemical compound C1=CC(N)=CC=C1COC1=CC=C(N)C=C1 VYYVHHWQRAEFOL-UHFFFAOYSA-N 0.000 description 1
- GTVWIHJYRMAQTL-UHFFFAOYSA-N 4h-carbazole Chemical compound C1=CC=CC2=C3CC=CC=C3N=C21 GTVWIHJYRMAQTL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- AVXTUOKLXHIKLA-UHFFFAOYSA-N CC(C1=CC=CC(C(C)=NN2C(C)=NN(C)C2)=N1)=NN1C(C)=NN(C)C1 Chemical compound CC(C1=CC=CC(C(C)=NN2C(C)=NN(C)C2)=N1)=NN1C(C)=NN(C)C1 AVXTUOKLXHIKLA-UHFFFAOYSA-N 0.000 description 1
- 0 CC1=CC(C(C=*)=O)PC1C(*)=O Chemical compound CC1=CC(C(C=*)=O)PC1C(*)=O 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical group CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
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- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- JCRZHGKOIVMLNR-UHFFFAOYSA-N bis(hydroxymethyl)alumanylmethanol Chemical compound OC[Al](CO)CO JCRZHGKOIVMLNR-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- TUECYXSPDUWZFF-UHFFFAOYSA-N hydrazinecarbonyl benzoate Chemical compound NNC(=O)OC(=O)C1=CC=CC=C1 TUECYXSPDUWZFF-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- YYGLMKYYNNDZLA-UHFFFAOYSA-N iron;2-methyl-3-propan-2-yl-1h-pyrrole Chemical compound [Fe].CC(C)C=1C=CNC=1C YYGLMKYYNNDZLA-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- VAQAENXMAMHZEV-UHFFFAOYSA-N n,n-diphenyl-1h-pyrrol-2-amine Chemical compound C1=CNC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 VAQAENXMAMHZEV-UHFFFAOYSA-N 0.000 description 1
- NAOKKJATLKPZMH-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[6-[n-(2,6-dimethylphenyl)-c-methylcarbonimidoyl]pyridin-2-yl]ethanimine Chemical compound C=1C=CC(C(C)=NC=2C(=CC=CC=2C)C)=NC=1C(C)=NC1=C(C)C=CC=C1C NAOKKJATLKPZMH-UHFFFAOYSA-N 0.000 description 1
- BQKQZTGYYJBGHS-UHFFFAOYSA-N n-pyrrol-1-ylacetamide Chemical compound CC(=O)NN1C=CC=C1 BQKQZTGYYJBGHS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940054334 silver cation Drugs 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19939415 | 1999-08-20 | ||
| DE19939415.6 | 1999-08-20 | ||
| PCT/EP2000/007657 WO2001014391A1 (de) | 1999-08-20 | 2000-08-08 | Bisimidinoverbindungen und ihre übergangsmetallkomplexe sowie deren verwendung als katalysatoren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003507483A JP2003507483A (ja) | 2003-02-25 |
| JP2003507483A5 JP2003507483A5 (enExample) | 2006-03-16 |
| JP3907475B2 true JP3907475B2 (ja) | 2007-04-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001518721A Expired - Fee Related JP3907475B2 (ja) | 1999-08-20 | 2000-08-08 | 不飽和化合物の重合用触媒 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6818715B1 (enExample) |
| EP (1) | EP1204668B1 (enExample) |
| JP (1) | JP3907475B2 (enExample) |
| KR (1) | KR20020023421A (enExample) |
| AT (1) | ATE236180T1 (enExample) |
| DE (1) | DE50001649D1 (enExample) |
| WO (1) | WO2001014391A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000050470A2 (en) | 1999-02-22 | 2000-08-31 | Eastman Chemical Company | Catalysts containing n-pyrrolyl substituted nitrogen donors |
| US6545108B1 (en) | 1999-02-22 | 2003-04-08 | Eastman Chemical Company | Catalysts containing N-pyrrolyl substituted nitrogen donors |
| US6579823B2 (en) | 2000-02-18 | 2003-06-17 | Eastman Chemical Company | Catalysts containing per-ortho aryl substituted aryl or heteroaryl substituted nitrogen donors |
| US7056996B2 (en) | 2000-02-18 | 2006-06-06 | E. I. Du Pont De Nemours And Company | Productivity catalysts and microstructure control |
| US6605677B2 (en) | 2000-02-18 | 2003-08-12 | Eastman Chemical Company | Olefin polymerization processes using supported catalysts |
| DE10017666A1 (de) * | 2000-04-08 | 2001-10-11 | Basf Ag | Verfahren zur Herstellung eines geträgerten Katalysators zur Polymerisation von Olefinen |
| US6706891B2 (en) | 2000-11-06 | 2004-03-16 | Eastman Chemical Company | Process for the preparation of ligands for olefin polymerization catalysts |
| GB0112023D0 (en) * | 2001-05-17 | 2001-07-11 | Bp Chem Int Ltd | Polymerisation catalyst |
| CN1142142C (zh) * | 2001-06-01 | 2004-03-17 | 中国科学院上海有机化学研究所 | 乙烯齐聚催化剂、合成方法和用途 |
| GB0306418D0 (en) | 2003-03-20 | 2003-04-23 | Exxonmobil Chem Patents Inc | Catalyst composition |
| GB0312063D0 (en) | 2003-05-27 | 2003-07-02 | Exxonmobil Chem Patents Inc | Catalyst composition II |
| US7268096B2 (en) * | 2005-07-21 | 2007-09-11 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| US7271121B2 (en) * | 2005-07-21 | 2007-09-18 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| US7129304B1 (en) | 2005-07-21 | 2006-10-31 | Chevron Phillips Chemical Company Lp | Dimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| US7727926B2 (en) * | 2005-07-21 | 2010-06-01 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and method of using in oligomerization and polymerization |
| JP5424484B2 (ja) * | 2010-02-03 | 2014-02-26 | 矢崎総業株式会社 | コネクタ |
| US9586872B2 (en) | 2011-12-30 | 2017-03-07 | Chevron Phillips Chemical Company Lp | Olefin oligomerization methods |
| US9944661B2 (en) | 2016-08-09 | 2018-04-17 | Chevron Phillips Chemical Company Lp | Olefin hydroboration |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0627448T3 (da) | 1990-01-02 | 2000-05-22 | Exxon Chemical Patents Inc | Ioniske metallocenkatalysatorer på bærere til olefinpolymerisation |
| IL129929A0 (en) * | 1996-12-17 | 2000-02-29 | Du Pont | Polymerization of ethylene with specific iron or cobalt complexes novel pyridinebis (imines) and novel complexes of pyridinebis(imines) with iron and cobalt |
| US6150482A (en) * | 1997-01-13 | 2000-11-21 | E. I. Du Pont De Nemours And Company | Polymerization of propylene |
| PT1015501E (pt) | 1997-09-05 | 2002-11-29 | Bp Chem Int Ltd | Catalisadores de polimerizacao |
| ID27209A (id) * | 1998-03-12 | 2001-03-08 | Bp Chem Int Ltd | Katalis-katalis polimerisasi |
| GB9819847D0 (en) | 1998-09-12 | 1998-11-04 | Bp Chem Int Ltd | Novel compounds |
| WO2000020427A1 (en) | 1998-10-02 | 2000-04-13 | Bp Chemicals Limited | Polymerisation catalysts |
| WO2000050470A2 (en) | 1999-02-22 | 2000-08-31 | Eastman Chemical Company | Catalysts containing n-pyrrolyl substituted nitrogen donors |
| GB9906296D0 (en) * | 1999-03-18 | 1999-05-12 | Bp Chem Int Ltd | Polymerisation catalysts |
| US6281303B1 (en) * | 1999-07-27 | 2001-08-28 | Eastman Chemical Company | Olefin oligomerization and polymerization catalysts |
| EP1542797B1 (en) * | 2002-09-25 | 2006-05-31 | Shell Internationale Researchmaatschappij B.V. | Catalyst systems for ethylene oligomerisation to linear alpha olefins |
-
2000
- 2000-08-08 EP EP00956407A patent/EP1204668B1/de not_active Expired - Lifetime
- 2000-08-08 JP JP2001518721A patent/JP3907475B2/ja not_active Expired - Fee Related
- 2000-08-08 DE DE50001649T patent/DE50001649D1/de not_active Expired - Lifetime
- 2000-08-08 AT AT00956407T patent/ATE236180T1/de not_active IP Right Cessation
- 2000-08-08 KR KR1020027002122A patent/KR20020023421A/ko not_active Withdrawn
- 2000-08-08 WO PCT/EP2000/007657 patent/WO2001014391A1/de not_active Ceased
- 2000-08-08 US US10/049,861 patent/US6818715B1/en not_active Expired - Lifetime
-
2004
- 2004-10-07 US US10/959,212 patent/US7273940B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003507483A (ja) | 2003-02-25 |
| KR20020023421A (ko) | 2002-03-28 |
| EP1204668A1 (de) | 2002-05-15 |
| DE50001649D1 (de) | 2003-05-08 |
| US7273940B2 (en) | 2007-09-25 |
| WO2001014391A1 (de) | 2001-03-01 |
| US20050085527A1 (en) | 2005-04-21 |
| US6818715B1 (en) | 2004-11-16 |
| ATE236180T1 (de) | 2003-04-15 |
| EP1204668B1 (de) | 2003-04-02 |
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