JP6876702B2 - ニッケル、ホスフィン型配位子およびルイス塩基を含む触媒組成物とオレフィンオリゴマー化法におけるその使用 - Google Patents
ニッケル、ホスフィン型配位子およびルイス塩基を含む触媒組成物とオレフィンオリゴマー化法におけるその使用 Download PDFInfo
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- JP6876702B2 JP6876702B2 JP2018530900A JP2018530900A JP6876702B2 JP 6876702 B2 JP6876702 B2 JP 6876702B2 JP 2018530900 A JP2018530900 A JP 2018530900A JP 2018530900 A JP2018530900 A JP 2018530900A JP 6876702 B2 JP6876702 B2 JP 6876702B2
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- Prior art keywords
- nickel
- group
- composition according
- phosphine ligand
- chloride
- Prior art date
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims description 83
- 239000000203 mixture Substances 0.000 title claims description 57
- 229910052759 nickel Inorganic materials 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 34
- 239000003446 ligand Substances 0.000 title claims description 28
- 150000001336 alkenes Chemical class 0.000 title claims description 22
- 239000002879 Lewis base Substances 0.000 title claims description 20
- 150000007527 lewis bases Chemical class 0.000 title claims description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 18
- 230000003197 catalytic effect Effects 0.000 title claims description 12
- 238000006384 oligomerization reaction Methods 0.000 title description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 60
- -1 hydrocarbyl aluminum Chemical compound 0.000 claims description 36
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 23
- 239000002243 precursor Substances 0.000 claims description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
- 239000005977 Ethylene Substances 0.000 claims description 16
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 15
- 239000012190 activator Substances 0.000 claims description 11
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 10
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- YBMAWNCLJNNCMV-BUOKYLHBSA-L (e)-1,1,1,5,5,5-hexafluoro-4-oxopent-2-en-2-olate;nickel(2+) Chemical compound [Ni+2].FC(F)(F)C(/[O-])=C\C(=O)C(F)(F)F.FC(F)(F)C(/[O-])=C\C(=O)C(F)(F)F YBMAWNCLJNNCMV-BUOKYLHBSA-L 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- OIVXTXJBUBYQDC-UHFFFAOYSA-L O1C(=CC=C1)C(=O)[O-].O1C(=CC=C1)C(=O)O.O1C(=CC=C1)C(=O)[O-].[Ni+2] Chemical compound O1C(=CC=C1)C(=O)[O-].O1C(=CC=C1)C(=O)O.O1C(=CC=C1)C(=O)[O-].[Ni+2] OIVXTXJBUBYQDC-UHFFFAOYSA-L 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 238000006471 dimerization reaction Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims description 4
- UNMGLSGVXHBBPH-BVHINDLDSA-L nickel(2+) (NE)-N-[(3E)-3-oxidoiminobutan-2-ylidene]hydroxylamine Chemical compound [Ni++].C\C(=N/O)\C(\C)=N\[O-].C\C(=N/O)\C(\C)=N\[O-] UNMGLSGVXHBBPH-BVHINDLDSA-L 0.000 claims description 4
- VBLNFWKVZVKXPH-UHFFFAOYSA-L nickel(2+);2,2,2-trifluoroacetate Chemical compound [Ni+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F VBLNFWKVZVKXPH-UHFFFAOYSA-L 0.000 claims description 4
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 claims description 4
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 claims description 4
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims description 4
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 claims description 4
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 3
- 238000007037 hydroformylation reaction Methods 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 claims description 3
- 229910021508 nickel(II) hydroxide Inorganic materials 0.000 claims description 3
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 claims description 3
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000446 fuel Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- MKZIDVHSSGEADY-UHFFFAOYSA-L hexanoate;nickel(2+) Chemical compound [Ni+2].CCCCCC([O-])=O.CCCCCC([O-])=O MKZIDVHSSGEADY-UHFFFAOYSA-L 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- MWLSXFWPDXKUNB-UHFFFAOYSA-N nickel(2+) hydrochloride Chemical compound Cl.[Ni+2] MWLSXFWPDXKUNB-UHFFFAOYSA-N 0.000 claims 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 9
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002608 ionic liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000447 dimerizing effect Effects 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 150000002816 nickel compounds Chemical class 0.000 description 4
- 230000003606 oligomerizing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- RURZQVYCZPJWMN-UHFFFAOYSA-N 2-ethylhexanoic acid;nickel Chemical compound [Ni].CCCCC(CC)C(O)=O.CCCCC(CC)C(O)=O RURZQVYCZPJWMN-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexanol Substances CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910021587 Nickel(II) fluoride Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- MNSHGRXIICSKRQ-UHFFFAOYSA-L nickel(2+);3-oxobutanoate Chemical compound [Ni+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O MNSHGRXIICSKRQ-UHFFFAOYSA-L 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- YGUPAQDKOAPZHC-UHFFFAOYSA-N tricyclohexylphosphane Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 YGUPAQDKOAPZHC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
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Description
均質なニッケル触媒を用いたエチレンの変換は、1950年以来研究されている。この研究は、様々な方法の開発および商品化につながった。
本発明による触媒組成物は、
酸化数(+II)を有する少なくとも1つのニッケル前駆体と
式PR1R2R3を有する少なくとも1つのホスフィン配位子(式中、基R1、R2、R3は、同一であっても異なっていてもよく、一緒に結合していても結合していなくてもよく、
置換されていても置換されていなくてもよく、ヘテロ元素を含んでいても含んでいなくてもよい芳香族基、
環式であってもなくてもよく、置換されていても置換されていなくてもよく、またヘテロ元素を含有していても有していなくてもよいヒドロカルビル基、
から選択される)と、
少なくとも1つのルイス塩基と、を含み、
組成物は、5以下であるホスフィン配位子のニッケル前駆体に対するモル比と、5以上であるルイス塩基およびホスフィン配位子のニッケル前駆体に対するモル比と、を有する。
本発明による組成物は、オレフィンの水素化反応、ヒドロホルミル化反応、クロスカップリング、またはオリゴマー化などの化学変換反応における触媒として使用することができる。特に、これらの組成物は、有利には2〜10個の炭素原子を含むオレフィンの供給原料をオリゴマー化するための方法において、使用される。
反応器を最初に真空乾燥し、エチレンの雰囲気下に置いた。93mLのシクロヘキサンをエチレンの雰囲気下で反応器に導入した。次いで、Ni(2−EH)2と表すニッケル前駆体Ni(2−エチルヘキサノエート)2(10または20μmol)を含む溶液6mL、およびトリシクロヘキシルホスフィンPCy3(ニッケルに対して2または5モル当量)、およびピリジンまたはテトラヒドロフラン(ニッケルに対して5、8または10モル当量)を反応器に導入した。次いで、1〜2gのエチレンを反応器で溶解し、攪拌を開始し、温度を40℃にプログラムした。反応器を脱気した後、温度を50℃(試験温度)にプログラムした。次いで、エチルアルミニウムジクロリド(ニッケルに対して15モル当量)の溶液1mLを導入した。反応器を試験圧力(2MPa)まで加圧した。200gのエチレンが導入されるか、または反応が60分間行われるまで、エチレンの消費量を監視した。エチレンの供給を遮断した。気相を定量化し、ガスクロマトグラフィー(GC)によって定性化した。液相を秤量し、中和し、GCで定性化した。
触媒試験
実施例1〜3:比較例
Claims (16)
- 触媒組成物であって、
酸化数(+II)を有する少なくとも1つのニッケル前駆体と、
式PR1R2R3を有する少なくとも1つのホスフィン配位子(式中、基R1、R2、R3は、同一であっても異なっていてもよく、一緒に結合していても結合していなくてもよく、
置換されていても置換されていなくてもよく、ヘテロ元素を含んでいても含んでいなくてもよい芳香族基、
環式であってもなくてもよく、置換されていても置換されていなくてもよく、またヘテロ元素を含有していても有していなくてもよいヒドロカルビル基、
から選択される)と、
少なくとも1つのルイス塩基と、
単独でまたは混合物として使用される、ヒドロカルビルアルミニウムの塩素および臭素含有化合物によって形成された群から選択される活性化剤と、を含み、
5以下であるホスフィン配位子のニッケル前駆体に対するモル比と、5〜30の範囲であるルイス塩基およびホスフィン配位子のニッケル前駆体に対するモル比と、6以上である活性化剤のニッケル前駆体に対するモル比を有する、触媒組成物。 - 前記ホスフィン配位子の前記ニッケル前駆体に対する前記モル比が、2〜5の範囲にある、請求項1に記載の組成物。
- 前記ニッケル前駆体は、塩化ニッケル(II);塩化ニッケル(II)(ジメトキシエタン);臭化ニッケル(II);臭化ニッケル(II)(ジメトキシエタン);フッ化ニッケル(II);ヨウ化ニッケル(II);硫酸ニッケル(II);炭酸ニッケル(II);ニッケル(II)ジメチルグリオキシム;水酸化ニッケル(II);ヒドロキシ酢酸ニッケル(II);シュウ酸ニッケル(II);2−エチルヘキサン酸ニッケル(II)、酢酸ニッケル(II)、トリフルオロ酢酸ニッケル(II)、ニッケル(II)トリフラート、ニッケル(II)アセチルアセトネート、ニッケル(II)ヘキサフルオロアセチルアセトネート、ニッケル(II)フェネートによって形成された群から選択されるカルボン酸ニッケル(II);塩化アリルニッケル(II);臭化アリルニッケル(II);塩化メタリルニッケル(II)二量体;アリルニッケル(II)ヘキサフルオロホスフェート;メタリルニッケル(II)ヘキサフルオロホスフェート;ビスシクロペンタジエニルニッケル(II);ビスアリルニッケル(II)およびビスメタリルニッケル(II)から選択され、これらの水和形態またはそれ以外で、単独でまたは混合物として使用される、請求項1または2に記載の組成物。
- 前記ニッケル前駆体は、硫酸ニッケル(II);炭酸ニッケル(II);ニッケル(II)ジメチルグリオキシム;水酸化ニッケル(II)、ヒドロキシ酢酸ニッケル(II);シュウ酸ニッケル(II);2−エチルヘキサン酸ニッケル(II)、酢酸ニッケル(II)、トリフルオロ酢酸ニッケル(II)、ニッケル(II)トリフラート、ニッケル(II)アセチルアセトネート、ニッケル(II)ヘキサフルオロアセチルアセトネート、ニッケル(II)フェネートによって形成された群から選択されるカルボン酸ニッケル(II);アリルニッケル(II)ヘキサフルオロホスフェート;メタリルニッケル(II)ヘキサフルオロホスフェート;ニッケル(II);ビスアリルニッケル(II)およびビスメタリルニッケル(II)から選択され、これらの水和形態またはそれ以外で、単独でまたは混合物として使用される、請求項1または2に記載の組成物。
- 前記ホスフィン配位子の基R1、R2およびR3は同一である、請求項1〜4のいずれか一項に記載の組成物。
- 前記ホスフィン配位子PR1R2R3の前記芳香族基R1、R2およびR3は、フェニル基、o−トリル基、m−トリル基、p−トリル基、メシチル基、3,5−ジメチルフェニル基、4−n−ブチルフェニル基、4−メトキシフェニル基、2−メトキシフェニル基
、3−メトキシフェニル基、4−メトキシフェニル基、2−イソプロポキシフェニル基、4−メトキシ−3,5−ジメチルフェニル基、3,5−ジ−tert−ブチル−4−メトキシフェニル基、4−クロロフェニル基、3,5−ジ(トリフルオロメチル)フェニル基、ベンジル基、ナフチル基、ビスナフチル基、ピリジル基、ビスフェニル基、フラニル基およびチオフェニル基によって形成された群から選択される、請求項1〜5のいずれか一項に記載の組成物。 - 前記ホスフィン配位子PR1R2R3のヒドロカルビル基R1、R2およびR3は、1〜20個の炭素原子を含む、請求項1〜6のいずれか一項に記載の組成物。
- 前記ホスフィン配位子PR1R2R3の前記ヒドロカルビル基R1、R2およびR3は、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、tert−ブチル基、シクロペンチル基、シクロヘキシル基、ベンジル基、アダマンチル基によって形成された群から選択される、請求項7に記載の組成物。
- 前記ルイス塩基が、ジエチルエーテル、メチルtert−ブチルエーテル、テトラヒドロフラン、1,4−ジオキサン、イソキサゾール、ピリジン、ピラジン、およびピリミジンから選択される、請求項1〜8のいずれか一項に記載の組成物。
- 前記活性化剤は、メチルアルミニウムジクロリド(MeAlCl2)、エチルアルミニウムジクロリド(EtAlCl2)、エチルアルミニウムセスキクロリド(Et3Al2Cl3)、ジエチルアルミニウムクロリド(Et2AlCl)、ジイソブチルアルミニウムクロリド(iBu2AlCl)、およびイソブチルアルミニウムジクロリド(iBuAlCl2)によって形成された群から選択され、単独でまたは混合物として使用される、請求項9に記載の組成物。
- 前記ホスフィン配位子に対する前記活性化剤の前記モル比が、1以上である、請求項9または10に記載の組成物。
- オレフィン供給原料を請求項1〜11のいずれか一項に記載の組成物と接触させることを含む、前記供給原料をオリゴマー化するための方法。
- 前記供給原料は、2〜10個の範囲の炭素原子を含むオレフィンを含む、請求項12に記載の方法。
- 閉鎖系、半開放系、連続的またはバッチ式で行われる、請求項12または13に記載の方法。
- 前記方法は、エチレンを二量化するための方法である、請求項12〜14のいずれか一項に記載の方法。
- 自動車用燃料の成分として、アルデヒドおよびアルコールの合成のためのヒドロホルミル化方法における供給原料として、化学、石油化学、製薬、または香水産業用の成分として、プロピレンの合成のためのメタセシス方法における供給原料として、および/または酸化的脱水素化を介して若しくは金属触媒のステップを介してブタジエンを製造するための方法のための供給原料としての、請求項12〜15のいずれか一項に記載の方法からの生成物の使用。
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PCT/EP2016/080737 WO2017102689A1 (fr) | 2015-12-18 | 2016-12-13 | Composition catalytique a base de nickel et de ligand de type phosphine et d'une base de lewis et son utilisation dans un procede d'oligomerisation des olefines |
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FR3039430B1 (fr) * | 2015-07-29 | 2019-07-05 | IFP Energies Nouvelles | Nouvelle composition catalytique a base de nickel et de ligand de type phosphine et son utilisation dans un procede d'oligomerisation des olefines |
FR3068621B1 (fr) | 2017-07-10 | 2020-06-26 | IFP Energies Nouvelles | Procede d’oligomerisation mettant en oeuvre un vortex |
FR3068620B1 (fr) | 2017-07-10 | 2020-06-26 | IFP Energies Nouvelles | Procede d’oligomerisation mettant en oeuvre un dispositf reactionnel comprenant un moyen de dispersion |
FR3083235B1 (fr) | 2018-06-29 | 2021-12-03 | Ifp Energies Now | Procede d'oligomerisation en cascade de reacteurs gaz liquide agites avec injection etagee d'ethylene |
FR3086288A1 (fr) | 2018-09-21 | 2020-03-27 | IFP Energies Nouvelles | Procede d'oligomerisation d'ethylene dans un reacteur gaz/liquide compartimente |
FR3086551A1 (fr) * | 2018-09-28 | 2020-04-03 | IFP Energies Nouvelles | Composition catalytique a base de nickel (ii) |
FR3096587B1 (fr) | 2019-05-28 | 2021-06-11 | Ifp Energies Now | Reacteur d’oligomerisation compartimente |
FR3099476B1 (fr) | 2019-07-31 | 2021-07-30 | Ifp Energies Now | Procede d’oligomerisation mettant en œuvre un recycle du ciel gazeux |
FR3102685B1 (fr) | 2019-11-06 | 2021-10-29 | Ifp Energies Now | Procédé d’oligomérisation d’oléfines dans un réacteur d’oligomérisation |
FR3105018B1 (fr) | 2019-12-18 | 2021-12-10 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation comprenant des internes transversaux |
FR3105019B1 (fr) | 2019-12-18 | 2022-07-22 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation a zones successives de diametre variable |
FR3108264B1 (fr) | 2020-03-19 | 2022-04-08 | Ifp Energies Now | Installation d’oligomérisation d’éthylène pour produire des alpha-oléfines |
FR3112342A1 (fr) | 2020-07-09 | 2022-01-14 | IFP Energies Nouvelles | Procede d’oligomerisation mettant en œuvre un echangeur gaz/liquide |
FR3112775B1 (fr) | 2020-07-24 | 2022-07-01 | Ifp Energies Now | Procédé d’oligomérisation mettant en oeuvre un recycle du ciel gazeux |
FR3117890B1 (fr) | 2020-12-23 | 2024-01-12 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation comprenant un double distributeur gaz/liquide |
FR3117891A1 (fr) | 2020-12-23 | 2022-06-24 | IFP Energies Nouvelles | Reacteur gaz/liquide d’oligomerisation comprenant une conduite centrale |
FR3121439B1 (fr) | 2021-03-30 | 2023-03-24 | Ifp Energies Now | Procede d'oligomerisation comprenant une etape de recyclage d'un solvant prealablement refroidi |
FR3123354B1 (fr) | 2021-05-28 | 2023-05-26 | Ifp Energies Now | Procede d'oligomerisation dans un reacteur a zones de diametres variables comprenant une etape de recyclage d'un solvant prealablement refroidi |
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JPS62187434A (ja) * | 1986-02-12 | 1987-08-15 | Asahi Chem Ind Co Ltd | ジフエニルカルボン酸エステルの製造法 |
JPH0678263B2 (ja) * | 1986-07-01 | 1994-10-05 | 旭化成工業株式会社 | 4―(パラフルオロベンゾイル)フェノール類の製造方法 |
FR2650760B1 (fr) * | 1989-08-08 | 1991-10-31 | Inst Francais Du Petrole | Nouvelle composition catalytique et sa mise en oeuvre pour l'oligomerisation des monoolefines |
JPH0429957A (ja) * | 1990-05-25 | 1992-01-31 | Ihara Chem Ind Co Ltd | ビアリール誘導体の製造方法 |
US5166114A (en) * | 1992-01-14 | 1992-11-24 | Phillips Petroleum Company | Ethylene dimerization and catalyst therefor |
DE69423165T2 (de) * | 1993-09-22 | 2000-07-06 | Inst Francais Du Petrole | Nickel enthaltende Katalysatorzusammensetzung und Verfahren zum Dimerisieren und Oligomerisieren von Olefinen |
CN1077577C (zh) * | 1997-10-31 | 2002-01-09 | 中国石油化工总公司 | 乙烯二聚催化剂及由其与乙烯聚合催化剂组成的催化剂体系 |
US7354880B2 (en) * | 1998-07-10 | 2008-04-08 | Univation Technologies, Llc | Catalyst composition and methods for its preparation and use in a polymerization process |
US6825148B2 (en) * | 2001-04-10 | 2004-11-30 | Shell Oil Company | Nickel-containing ethylene oligomerization catalyst and use thereof |
US7232869B2 (en) * | 2005-05-17 | 2007-06-19 | Novolen Technology Holdings, C.V. | Catalyst composition for olefin polymerization |
EP2239056B1 (en) * | 2009-04-09 | 2011-07-20 | Saudi Basic Industries Corporation | Catalyst composition and process for oligomerization of ethylene |
FR2979836B1 (fr) * | 2011-09-08 | 2014-08-08 | IFP Energies Nouvelles | Nouvelle composition catalytique a base de nickel et procede d'oligomerisation des olefines utilisant ladite composition |
FR3020285B1 (fr) * | 2014-04-28 | 2017-12-08 | Ifp Energies Now | Nouvelle composition catalytique a base de nickel et son utilisation dans un procede d'oligomerisation des olefines |
FR3020286B1 (fr) * | 2014-04-28 | 2017-12-08 | Ifp Energies Now | Nouveaux complexes a base de nickel et leur utilisation dans un procede de transformations des olefines |
FR3020287B1 (fr) * | 2014-04-28 | 2017-12-08 | Ifp Energies Now | Nouveaux complexes cycliques a base de nickel et leur utilisation dans un procede de transformation des olefines |
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