JP6828161B2 - オレフィン多量化用触媒およびその触媒存在下で行うオレフィン多量体の製造方法 - Google Patents
オレフィン多量化用触媒およびその触媒存在下で行うオレフィン多量体の製造方法 Download PDFInfo
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- JP6828161B2 JP6828161B2 JP2019527978A JP2019527978A JP6828161B2 JP 6828161 B2 JP6828161 B2 JP 6828161B2 JP 2019527978 A JP2019527978 A JP 2019527978A JP 2019527978 A JP2019527978 A JP 2019527978A JP 6828161 B2 JP6828161 B2 JP 6828161B2
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- olefin
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- 150000001336 alkenes Chemical class 0.000 title claims description 86
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 72
- 239000003054 catalyst Substances 0.000 title claims description 57
- 238000004519 manufacturing process Methods 0.000 title claims description 41
- -1 Amine compound Chemical class 0.000 claims description 183
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 56
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 55
- 150000002430 hydrocarbons Chemical group 0.000 claims description 47
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 32
- 239000005977 Ethylene Substances 0.000 claims description 32
- 229910052782 aluminium Inorganic materials 0.000 claims description 32
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 24
- 229910052796 boron Inorganic materials 0.000 claims description 23
- 150000001845 chromium compounds Chemical class 0.000 claims description 22
- 150000002902 organometallic compounds Chemical class 0.000 claims description 22
- 238000011002 quantification Methods 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 19
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 16
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- 239000010703 silicon Substances 0.000 claims description 16
- 229910052718 tin Inorganic materials 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 150000002391 heterocyclic compounds Chemical group 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- 229910052732 germanium Inorganic materials 0.000 claims description 14
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 14
- 239000011574 phosphorus Substances 0.000 claims description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 150000003623 transition metal compounds Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000002216 antistatic agent Substances 0.000 claims description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 49
- 238000000034 method Methods 0.000 description 43
- 229910052723 transition metal Inorganic materials 0.000 description 39
- 150000003624 transition metals Chemical class 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 239000002253 acid Substances 0.000 description 19
- 150000008040 ionic compounds Chemical class 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000011651 chromium Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 12
- 229910052804 chromium Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000004927 clay Substances 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000011282 treatment Methods 0.000 description 11
- 150000002894 organic compounds Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000002734 clay mineral Substances 0.000 description 9
- 150000008282 halocarbons Chemical group 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 125000005234 alkyl aluminium group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical class 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 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 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
- 150000001638 boron Chemical group 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical class 0.000 description 4
- 125000003368 amide group Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000005110 aryl thio group Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000005462 imide group Chemical class 0.000 description 4
- 125000001841 imino group Chemical class [H]N=* 0.000 description 4
- 229910001502 inorganic halide Inorganic materials 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 4
- 125000000565 sulfonamide group Chemical class 0.000 description 4
- 150000007970 thio esters Chemical class 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 3
- 230000003416 augmentation Effects 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- 125000004185 ester group Chemical class 0.000 description 3
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 3
- 229910000271 hectorite Inorganic materials 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 238000009830 intercalation Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- JYLPOJPHFDVWCY-UHFFFAOYSA-K oxolane;trichlorochromium Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3].C1CCOC1 JYLPOJPHFDVWCY-UHFFFAOYSA-K 0.000 description 3
- 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 3
- 239000002245 particle Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 125000004469 siloxy group Chemical class [SiH3]O* 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VASOMTXTRMYSKD-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boronic acid Chemical compound OB(O)C1=C(F)C(F)=C(F)C(F)=C1F VASOMTXTRMYSKD-UHFFFAOYSA-N 0.000 description 2
- HTGQCLJTWPSFNL-UHFFFAOYSA-N (2-methylphenoxy)boronic acid Chemical compound CC1=CC=CC=C1OB(O)O HTGQCLJTWPSFNL-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- QWQBQRYFWNIDOC-UHFFFAOYSA-N (3,5-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC(F)=CC(F)=C1 QWQBQRYFWNIDOC-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- QPKFVRWIISEVCW-UHFFFAOYSA-N 1-butane boronic acid Chemical compound CCCCB(O)O QPKFVRWIISEVCW-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XDQJFSBPXSJQEJ-UHFFFAOYSA-N BBBBBBCCB Chemical compound BBBBBBCCB XDQJFSBPXSJQEJ-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 229910010199 LiAl Inorganic materials 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 229920000463 Poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical class 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000005336 allyloxy group Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000000223 arsonoyl group Chemical group [H][As](*)(*)=O 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-UHFFFAOYSA-N 0.000 description 1
- FHAOCGKAMRAFMM-UHFFFAOYSA-N tris(2-ethylhexyl)alumane Chemical compound CCCCC(CC)C[Al](CC(CC)CCCC)CC(CC)CCCC FHAOCGKAMRAFMM-UHFFFAOYSA-N 0.000 description 1
- FXDRTQPEGDSVEA-UHFFFAOYSA-N tris(2-methylbutyl)alumane Chemical compound CCC(C)C[Al](CC(C)CC)CC(C)CC FXDRTQPEGDSVEA-UHFFFAOYSA-N 0.000 description 1
- PPJMJDLVYZBVEP-UHFFFAOYSA-N tris(2-methylhexyl)alumane Chemical compound CCCCC(C)C[Al](CC(C)CCCC)CC(C)CCCC PPJMJDLVYZBVEP-UHFFFAOYSA-N 0.000 description 1
- YFDAMRSZJLWUSQ-UHFFFAOYSA-N tris(2-methylphenyl)borane Chemical compound CC1=CC=CC=C1B(C=1C(=CC=CC=1)C)C1=CC=CC=C1C YFDAMRSZJLWUSQ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- AGOOAFIKKUZTEB-UHFFFAOYSA-N tris(3,5-difluorophenyl)borane Chemical compound FC1=CC(F)=CC(B(C=2C=C(F)C=C(F)C=2)C=2C=C(F)C=C(F)C=2)=C1 AGOOAFIKKUZTEB-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
- MKABHRPSDIJZCK-UHFFFAOYSA-N tris(3-methylhexyl)alumane Chemical compound CCCC(C)CC[Al](CCC(C)CCC)CCC(C)CCC MKABHRPSDIJZCK-UHFFFAOYSA-N 0.000 description 1
- KBDPCSBGWWKZNI-UHFFFAOYSA-N tris(3-methylpentyl)alumane Chemical compound CCC(C)CC[Al](CCC(C)CC)CCC(C)CC KBDPCSBGWWKZNI-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
- MLDSMTVYPPIXMZ-UHFFFAOYSA-N tris(4-methylpentyl)alumane Chemical compound CC(C)CCC[Al](CCCC(C)C)CCCC(C)C MLDSMTVYPPIXMZ-UHFFFAOYSA-N 0.000 description 1
- LEIHCYASDULBKZ-UHFFFAOYSA-N tris(4-methylphenyl)borane Chemical compound C1=CC(C)=CC=C1B(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LEIHCYASDULBKZ-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
- RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910006592 α-Sn Inorganic materials 0.000 description 1
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of chromium, molybdenum or tungsten
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- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
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- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
- B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
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- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
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- B01J2231/20—Olefin oligomerisation or telomerisation
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- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
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- C07C2531/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Catalysts (AREA)
Description
(A)ハロゲン含有クロム化合物
(B)下記一般式(1)で表されるアミン化合物
Yは、置換基R5およびR6を有する炭素原子(−CR5R6−で表される構造)を示す。R5およびR6は、互いに同一でも異なっていてもよく、水素原子、ハロゲン原子、炭化水素基、ヘテロ環式化合物残基、酸素含有基、窒素含有基、ホウ素含有基、アルミニウム含有基、イオウ含有基、リン含有基、ケイ素含有基、ゲルマニウム含有基、またはスズ含有基を示し、R5とR6は互いに連結していてもよく、またR1〜R4の何れかと連結していてもよい。
Zは1〜10の整数を示す。)
(C)(C−1)有機金属化合物、
(C−2)有機アルミニウムオキシ化合物、および、
(C−3)遷移金属化合物と反応してイオン対を形成する化合物からなる群より選択される少なくとも1種の化合物。
(D)成分(A)〜(C)からなる群より選択される少なくとも1種の化合物を担持するための担体。
(A)ハロゲン含有クロム化合物
(B)下記一般式(1)で表されるアミン化合物
Yは、置換基R5およびR6を有する炭素原子(−CR5R6−で表される構造)を示す。R5およびR6は、互いに同一でも異なっていてもよく、水素原子、ハロゲン原子、炭化水素基、ヘテロ環式化合物残基、酸素含有基、窒素含有基、ホウ素含有基、アルミニウム含有基、イオウ含有基、リン含有基、ケイ素含有基、ゲルマニウム含有基、またはスズ含有基を示し、R5とR6は互いに連結していてもよく、またR1〜R4の何れかと連結していてもよい。
Zは1〜10の整数を示す。)
(C)(C−1)有機金属化合物、
(C−2)有機アルミニウムオキシ化合物、および、
(C−3)遷移金属化合物と反応してイオン対を形成する化合物からなる群より選択される少なくとも1種の化合物。
本発明に用いるクロム化合物(A)は、通常、クロムの無機塩、有機塩または金属有機錯体である。クロム化合物(A)の具体例としては、塩化クロム(III)、塩化クロム(II)、臭化クロム(III)、臭化クロム(II)、ヨウ化クロム(III)、ヨウ化クロム(II)、フッ化クロム(III)、フッ化クロム(II)、三塩化クロムトリステトラヒドロフラン、クロム(III)2−エチルヘキサノエート、クロム(III)アセチルアセトナート、クロム(III)トリフルオロアセチルアセトナート、クロム(III)ヘキサフルオロアセチルアセトナートが挙げられる。ただし、クロム化合物(A)はこれらに限定されない。これらの中では、3価のクロム化合物が好ましい。また、ハロゲン原子を含有するクロム化合物も好ましい。
本発明に用いるアミン化合物(B)は、下記一般式(1)で表される。
本発明に用いる化合物(C)は、有機金属化合物(C−1)、有機アルミニウムオキシ化合物(C−2)および遷移金属化合物と反応してイオン対を形成する化合物(C−3)からなる群より選択される少なくとも1種の化合物である。以下、これら化合物(C−1)〜(C−3)について説明する。以下の記載において、化合物(C−3)は「イオン化イオン性化合物(C−3)」と記す。
有機金属化合物(C−1)としては、例えば、以下に記載する化合物(C−1a)、(C−1b)および(C−1c)のような周期律表第1、2、12、13族の有機金属化合物を使用できる。本発明において、有機金属化合物(C−1)には後述する有機アルミニウムオキシ化合物(C−2)は含まれないものとする。
有機アルミニウムオキシ化合物(C−2)は、従来公知のアルミノキサンであってもよく、また特開平2−78687号公報に例示されているようなベンゼン不溶性の有機アルミニウムオキシ化合物であってもよい。従来公知のアルミノキサンは、例えば以下の方法によって製造でき、通常、溶液として得られる。
(一般式(6)中、R7は上記一般式(5)におけるR7と同じ基を示す)
イオン化イオン性化合物(C−3)は、遷移金属化合物と反応してイオン対を形成する化合物である。したがって、少なくとも遷移金属化合物と接触させるとイオン対を形成する性質を有する化合物は、このイオン化イオン性化合物(C−3)に相当する。
本発明のオレフィン多量化用触媒は、担体(D)を含んでいてもよい。担体(D)は、無機化合物または有機化合物であって、通常、顆粒状または微粒子状の固体である。本発明において、担体(D)はクロム化合物(A)、アミン化合物(B)および/または化合物(C)を担持する。無機化合物としては、多孔質酸化物、無機ハロゲン化物、粘土、粘土鉱物、イオン交換性層状化合物が好ましい。
本発明のオレフィン多量化用触媒は、さらに必要に応じて有機化合物成分(E)を含んでいてもよい。
本発明のオレフィン多量化用触媒は、オレフィンの多量化反応に使用される触媒である。そのオレフィンの具体例としては、エチレン、プロピレン、1−ブテン、1−ペンテン、1−ヘキセン、4−メチル−1−ペンテン、ビニルシクロヘキセン、スチレン、1−オクテン、1−デセンなどのビニル化合物、2−ブテン、シクロペンテン、シクロヘキセン、ノルボルネンなどの内部オレフィンが挙げられる。中でも、エチレンが好ましい。2種以上のオレフィンを共多量化させてもよい。
本発明のオレフィン多量体の製造方法は、以上説明したオレフィン多量化用触媒の存在下でオレフィンの多量化反応(好ましくは3量化〜4量化反応、より好ましくは4量化反応)を行う方法である。
触媒活性は、単位時間当たりに得られた反応生成物の質量を、多量化に使用した遷移金属触媒成分中の遷移金属原子量(ミリモル)で除して求めた。
1−ヘキセンまたは1−オクテンの選択率は、以下の式に従い求めた。
S(%)=Wp/Wr×100
S(%):1−ヘキセンまたは1−オクテンの選択率(質量分率)
Wr(質量):反応により生成した炭素原子数が4以上からなる生成物の合計質量
Wp(質量):反応により生成した1−ヘキセンまたは1−オクテンの質量
[合成例1]
充分に乾燥した20mLの反応器に、ピロリジン2.1mL(25.4mmol)、37%ホルムアルデヒド水溶液1.0mL(13.3mmol)を仕込み、室温で撹拌した。17時間後、反応液にジエチルエーテルを添加して可溶分を抽出し、得られた分画を無水硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過した後、ろ液を減圧下溶媒留去した。得られた粗生成物を減圧蒸留することで、下記式(B−2)で表されるアミン化合物(以下化合物(1)という)1.32g(収率64%)を得た。
1H−NMR(270MHz,CD3COCD3):3.10(2H,s),2.52−2.43(8H,m),1.74−1.62(8H,m)ppm
充分に乾燥した20mLの反応器に、3−メチルピぺリジン3.2mL(27.0mmol)、37%ホルムアルデヒド水溶液1.0mL(13.3mmol)を0℃で仕込み、室温で撹拌した。18時間後、反応液にジエチルエーテルを添加して可溶分を抽出し、得られた分画を無水硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過した後、ろ液を減圧下溶媒留去した。得られた粗生成物を減圧蒸留することで、下記式(B−3)で表されるアミン化合物(以下化合物(2)という)1.95g(収率70%)を得た。
1H−NMR(270MHz,CD3COCD3):2.92−2.82(4H,m),2.74(2H,s),1.84−1.73(2H,m),1.71−1.37(10H,m),0.93−0.86(2H,m),0.85(3H,d,J=1.6Hz),0.83(3H,d,J=1.6Hz)ppm
充分に乾燥した20mLの反応器に、4−メチルピぺリジン3.2mL(26.6mmol)、37%ホルムアルデヒド水溶液1.0mL(13.3mmol)を0℃で仕込み、室温で撹拌した。17時間後、反応液にジエチルエーテルを添加して可溶分を抽出し、得られた分画を無水硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過した後、ろ液を減圧下溶媒留去した。得られた粗生成物を減圧蒸留することで、下記式(B−4)で表されるアミン化合物(以下化合物(3)という)2.00g(収率71%)を得た。
1H−NMR(270MHz,CD3COCD3):2.98−2.90(4H,m),2.76(2H,s),1.87−1.76(4H,m),1.59−1.54(4H,m),1.39−1.23(2H,m),1.19−1.04(4H,m),0.90(3H,d,J=2.7Hz),0.88(3H,d,J=2.7Hz)ppm
充分に乾燥した20mLの反応器に、N−エチルメチルアミン3.6mL(42.0mmol)、パラホルムアルデヒド0.63g(20.9mmol)、ジエチルエーテル3.4mLを仕込み、室温で撹拌した。92時間後、反応液を減圧下溶媒留去し、得られた粗生成物を減圧蒸留することで、下記式(B−5)で表されるアミン化合物(以下化合物(4)という)1.64g(収率60%)を得た。
1H−NMR(270MHz,CD3COCD3):2.79(2H,s),2.39(4H,q,J=7.3Hz),2.15(6H,s),0.98(6H,t,J=7.3Hz)ppm
充分に乾燥した20mLの反応器に、N−メチルプロピルアミン2.7mL(26.9mmol)、パラホルムアルデヒド0.40g(13.5mmol)、ジエチルエーテル1.8mLを仕込み、室温で撹拌した。116時間後、反応液を減圧下溶媒留去し、得られた粗生成物を減圧蒸留することで、下記式(B−6)で表されるアミン化合物(以下化合物(5)という)0.95g(収率45%)を得た。
1H−NMR(270MHz,CD3COCD3):2.79(2H,s),2.31(4H,t,J=7.3Hz),2.16(6H,s),1.44(4H,sext,J=7.3Hz),0.86(6H,t,J=7.3Hz)ppm
充分に乾燥した20mLの反応器に、N−メチルブチルアミン3.2mL(27.3mmol)、パラホルムアルデヒド0.40g(13.4mmol)、ジエチルエーテル1.8mLを仕込み、室温で撹拌した。118時間後、反応液を減圧下溶媒留去し、得られた粗生成物を減圧蒸留することで、下記式(B−7)で表されるアミン化合物(以下化合物(6)という)1.96g(収率78%)を得た。
1H−NMR(270MHz,CD3COCD3):2.78(2H,s),2.34(4H,t,J=7.3Hz),2.16(6H,s),1.48−1.24(8H,m),0.89(6H,t,J=7.3Hz)ppm
充分に乾燥した20mLの反応器に、N−メチルイソブチルアミン3.2mL(26.6mmol)、パラホルムアルデヒド0.40g(13.5mmol)、ジエチルエーテル1.8mLを仕込み、室温で撹拌した。94時間後、反応液を減圧下溶媒留去し、得られた粗生成物を減圧蒸留することで、下記式(B−8)で表されるアミン化合物(以下化合物(7)という)1.64g(収率65%)を得た。
1H−NMR(270MHz,CD3COCD3):2.77(2H,s),2.16(6H,s),2.10(4H,d,J=7.3Hz),1.77(2H,sept,J=6.5Hz),0.86(12H,d,J=6.5Hz)ppm
充分に乾燥した20mLの反応器に、N−メチル−n−オクチルアミン4.8mL(26.5mmol)、パラホルムアルデヒド0.41g(13.5mmol)、ジエチルエーテル1.8mLを仕込み、室温で撹拌した。116時間後、反応液を減圧下溶媒留去し、得られた粗生成物を減圧蒸留することで、下記式(B−9)で表されるアミン化合物(以下化合物(8)という)3.19g(収率79%)を得た。
1H−NMR(270MHz,CD3COCD3):2.78(2H,s),2.35(4H,t,J=6.8Hz),2.16(6H,s),1.44(4H,t,J=6.8Hz),1.29(20H,brs),0.87(6H,t,J=6.8Hz)ppm
[実施例1]
充分に乾燥した100mLのシュレンク管に、N,N,N',N'−テトラメチルジアミノメタン(アミン化合物(B−1))0.45g(4.38mmol)、三塩化クロムトリステトラヒドロフラン1.62g(4.18mmol)、ジクロロメタン80mLを加え、アルゴン雰囲気下で16時間撹拌した。反応液を減圧下約1/3まで濃縮した後、不溶分をガラスフィルターでろ取し、減圧乾燥することでクロム化合物0.79gを得た。分析の結果、クロム濃度は20.0質量%であった。このクロム化合物にメチルシクロヘキサンを加え、クロム原子換算で0.001mmol/mLのメチルシクロヘキサン溶液(触媒溶液)を調製した。
アミン化合物(B−1)の代わりにアミン化合物(B−2)〜(B−11)を用いたこと以外は、実施例1と同様にして反応を行った。結果を表1に示す。
アミン化合物(B−1)の代わりに下記式(O−1)、(O−2)および(P−1)で表される化合物(O−1)、(O−2)および(P−1)(いずれも市販品を常法で精製したもの)を用いたこと以外は、実施例1と同様にして反応を行った。結果を表2に示す。
充分に乾燥した100mLのシュレンク管に、アミン化合物(B−6)0.22g(1.39mmol)、三塩化クロムトリステトラヒドロフラン0.49g(1.31mmol)、ジクロロメタン24mLを加え、アルゴン雰囲気下で20時間撹拌した。反応液を減圧下約1/2まで濃縮した後、n−ヘキサンを15mL加えしばらく撹拌し、減圧下約2/3まで濃縮し不溶分をガラスフィルターでろ取した。n−ヘキサン20mLで洗浄後、減圧乾燥することでクロム化合物を0.26g得た。分析の結果クロムの濃度は16.5質量%であった。このクロム化合物にメチルシクロヘキサンを加え、クロム原子換算で0.001mmol/mLのメチルシクロヘキサン溶液(触媒溶液)を調製した。
アミン化合物(B−6)の代わりにアミン化合物(B−10)を用いたこと以外は、実施例12と同様にして反応を行った。低沸点成分の生成量(炭素原子数10以下のα−オレフィンの生成量)は17200mg、ポリエチレンの生成量は1400mgであり、これらの生成物量合計から算出した触媒活性は37200g−生成物/(mmol−Cr・hr)であった。低沸点成分のうち、1−ヘキセンの選択率は15.3質量%、1−オクテンの選択率は82.4質量%であり、1−オクテンの触媒活性は28346g−生成物/(mmol−Cr・hr)であった。結果を表3に示す。
反応温度を60℃から70℃に変更したこと以外は、実施例13と同様にして反応を行った。低沸点成分の生成量は24300mg、ポリエチレンの生成量は1200mgであり、これらの生成物量合計から算出した触媒活性は51000g−生成物/(mmol−Cr・hr)であった。低沸点成分のうち、1−ヘキセンの選択率は22.6質量%、1−オクテンの選択率は74.9質量%であり、1−オクテンの触媒活性は36401g−生成物/(mmol−Cr・hr)であった。結果を表3に示す。
Claims (13)
- 下記成分(A)〜(C)を含むオレフィン多量化用触媒の存在下で、オレフィン多量化反応を行うオレフィン多量体の製造方法。
(A)ハロゲン含有クロム化合物
(B)下記一般式(1)で表されるアミン化合物
Yは、置換基R5およびR6を有する炭素原子(−CR5R6−で表される構造)を示す。R5およびR6は、互いに同一でも異なっていてもよく、水素原子、ハロゲン原子、炭化水素基、ヘテロ環式化合物残基、酸素含有基、窒素含有基、ホウ素含有基、アルミニウム含有基、イオウ含有基、リン含有基、ケイ素含有基、ゲルマニウム含有基、またはスズ含有基を示し、R5とR6は互いに連結していてもよく、またR1〜R4の何れかと連結していてもよい。
Zは1〜10の整数を示す。)
(C)(C−1)有機金属化合物、
(C−2)有機アルミニウムオキシ化合物、および、
(C−3)遷移金属化合物と反応してイオン対を形成する化合物からなる群より選択される少なくとも1種の化合物。 - 一般式(1)において、R1はR3およびR4とは連結しておらず、R2はR3およびR4とは連結していないアミン化合物(B)を用いる請求項1に記載のオレフィン多量体の製造方法。
- 一般式(1)においてZが1〜3の整数であるアミン化合物(B)を用いる請求項1に記載のオレフィン多量体の製造方法。
- 一般式(1)においてZが1であるアミン化合物(B)を用いる請求項1に記載のオレフィン多量体の製造方法。
- 一般式(1)においてZが2〜10の整数であるアミン化合物(B)を用いる請求項1に記載のオレフィン多量体の製造方法。
- 成分(A)〜(C)に加えて、下記成分(D)を含む請求項1に記載のオレフィン多量体の製造方法。
(D)成分(A)〜(C)からなる群より選択される少なくとも1種の化合物を担持するための担体。 - 帯電防止剤の存在下で、オレフィンの多量化反応を行う請求項1に記載のオレフィン多量体の製造方法。
- オレフィンがエチレンである請求項1に記載のオレフィン多量体の製造方法。
- オレフィン多量体が1−オクテンである請求項1に記載のオレフィン多量体の製造方法。
- 下記成分(A)および(B)を含むオレフィン多量化用触媒。
(A)ハロゲン含有クロム化合物
(B)下記一般式(1)で表されるアミン化合物
Yは、置換基R5およびR6を有する炭素原子(−CR5R6−で表される構造)を示す。R5およびR6は、互いに同一でも異なっていてもよく、水素原子、ハロゲン原子、炭化水素基、ヘテロ環式化合物残基、酸素含有基、窒素含有基、ホウ素含有基、アルミニウム含有基、イオウ含有基、リン含有基、ケイ素含有基、ゲルマニウム含有基、またはスズ含有基を示し、R5とR6は互いに連結していてもよく、またR1〜R4の何れかと連結していてもよい。
Zは1〜10の整数を示す。) - 一般式(1)においてZが1である請求項10に記載のオレフィン多量化用触媒。
- 成分(A)が3価のハロゲン含有クロム化合物である請求項10に記載のオレフィン多量化用触媒。
- 成分(A)および(B)に加えて、下記成分(C)を含む請求項10に記載のオレフィン多量化用触媒。
(C)(C−1)有機金属化合物、
(C−2)有機アルミニウムオキシ化合物、および、
(C−3)遷移金属化合物と反応してイオン対を形成する化合物からなる群より選択される少なくとも1種の化合物。
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- 2018-07-06 JP JP2019527978A patent/JP6828161B2/ja active Active
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US11691136B2 (en) | 2023-07-04 |
EP3650429A1 (en) | 2020-05-13 |
JPWO2019009390A1 (ja) | 2020-07-02 |
EP3650429A4 (en) | 2021-03-31 |
WO2019009390A1 (ja) | 2019-01-10 |
KR20220110863A (ko) | 2022-08-09 |
SG11202000016XA (en) | 2020-01-30 |
KR20200026953A (ko) | 2020-03-11 |
US20200222886A1 (en) | 2020-07-16 |
CA3068805C (en) | 2023-05-16 |
CA3068805A1 (en) | 2019-01-10 |
CN115872822A (zh) | 2023-03-31 |
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