TWI756324B - 用於中和包含至少一種鹵化衍生物之烯烴二聚合催化系統之方法 - Google Patents
用於中和包含至少一種鹵化衍生物之烯烴二聚合催化系統之方法 Download PDFInfo
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- TWI756324B TWI756324B TW106144313A TW106144313A TWI756324B TW I756324 B TWI756324 B TW I756324B TW 106144313 A TW106144313 A TW 106144313A TW 106144313 A TW106144313 A TW 106144313A TW I756324 B TWI756324 B TW I756324B
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- Taiwan
- Prior art keywords
- olefin
- catalytic system
- oligomerization
- nitrile compound
- halogenated derivative
- Prior art date
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- 150000001336 alkenes Chemical class 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 42
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 31
- 238000006386 neutralization reaction Methods 0.000 title claims abstract description 11
- 238000006471 dimerization reaction Methods 0.000 title claims description 19
- -1 nitrile compound Chemical class 0.000 claims abstract description 33
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 53
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 32
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- SVPZJHKVRMRREG-UHFFFAOYSA-N cyclopentanecarbonitrile Chemical compound N#CC1CCCC1 SVPZJHKVRMRREG-UHFFFAOYSA-N 0.000 claims description 2
- 238000004508 fractional distillation Methods 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
- 230000003606 oligomerizing effect Effects 0.000 claims 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 16
- NFLLKCVHYJRNRH-UHFFFAOYSA-N 8-chloro-1,3-dimethyl-7H-purine-2,6-dione 2-(diphenylmethyl)oxy-N,N-dimethylethanamine Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 NFLLKCVHYJRNRH-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000004876 x-ray fluorescence Methods 0.000 description 2
- 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 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- OZHLXQFAHIYYDJ-UHFFFAOYSA-L 2-hydroxyacetate;nickel(2+) Chemical compound [Ni+2].OCC([O-])=O.OCC([O-])=O OZHLXQFAHIYYDJ-UHFFFAOYSA-L 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 229910021587 Nickel(II) fluoride Inorganic materials 0.000 description 1
- 229910021588 Nickel(II) iodide Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- PFRDRCIPKPEULG-UHFFFAOYSA-N imidazol-2-imine Chemical compound N=C1N=CC=N1 PFRDRCIPKPEULG-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 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 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
- 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 description 1
- QTOJRHLRJFVPJN-UHFFFAOYSA-L nickel(2+);diphenoxide Chemical compound C=1C=CC=CC=1O[Ni]OC1=CC=CC=C1 QTOJRHLRJFVPJN-UHFFFAOYSA-L 0.000 description 1
- DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 description 1
- KVRSDIJOUNNFMZ-UHFFFAOYSA-L nickel(2+);trifluoromethanesulfonate Chemical compound [Ni+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F KVRSDIJOUNNFMZ-UHFFFAOYSA-L 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- 229910021508 nickel(II) hydroxide Inorganic materials 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- 239000003960 organic solvent Substances 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- 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
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- 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
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
- C07C2/22—Metal halides; Complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- 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
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Abstract
本發明係關於一種用於中和烯烴低聚合催化系統之方法，該催化系統包含至少一種鹵化衍生物，其特徵在於使反應流出物與至少一種腈化合物接觸。
Description
本發明係關於一種用於中和烯烴低聚合催化系統之方法，尤其是用於烯烴二聚合之方法，該催化系統包含至少一種鹵化衍生物。
自20世紀50年代以來已研究利用一種基於過渡金屬、尤其基於鎳與一種鹵化活化劑(例如氯化烷基鋁)結合之均相催化劑轉化低碳烯烴。該研究引起多種方法之發展及商業化。 舉例而言，辛烯或己烯或壬烯各自地利用Axens之DimersolTM
方法(Revue de the Institut Français du Pétrole[Review of the French Oil Institute]，第37卷，第5期，1982年9月-10月，第639頁) 由丁烯二聚合或丙二醇低聚合製備。辛烯可經氫甲醯化反應接著氫化反應轉化成異壬醇，產量良好。此等C9醇(亦即含有9個碳原子)尤其用以合成用於PVC之鄰苯二甲酸酯類塑化劑。己烯或壬烯亦可用作一種辛烷值極好之燃料的一種基質。 開發能夠二聚合烯烴之催化系統涉及選擇過渡金屬及合適的配位體。在現有催化劑系統中，已研發出數種使用各種配位體的基於鎳之催化系統。尤其可被提及的實例係p-烯丙基鎳膦鹵化物與路易斯酸之錯合物，如法國專利FR 1 410 430 B中所描述；鎳膦鹵化物與路易斯酸之錯合物，如專利US 3 485 881 A中所描述；鎳與亞胺基-咪唑配位體錯合物，如法國專利FR 2 979 836 B中所描述；及鎳與鹵化烴基鋁之羧酸鹽，如專利US 3 321 546 A所描述。在該等方法中，事實證明有必要在反應結束時中和催化劑以避免反應以不希望的方式繼續。 專利FR 2 114 114 B描述一種用於使含有至少一種鹵化化合物之烯烴二聚合催化劑去活化的方法，涉及使反應流出物與無水氨或胺接觸。 專利US 4 642 408 B描述一種用於在含有鹵化化合物之催化劑存在下處理烯烴低聚合反應流出物的方法，其藉由在第一步驟(1)中以無水氨溶液處理該流出物，隨後在第二步驟(2)中以鹼金屬水溶液洗滌來達成，條件為該流出物在步驟(1)及步驟(2)之前或之後利用氧氣或含有氧氣的氣體處理該流出物。 描述於「先前技術」中的方法在中和效率方面係令人滿意的，但導致在安全方面的問題，此等問題與使用某些諸如氨或胺之抑制劑有關，詳言之因為其物理上呈氣態及/或其毒性。 申請人之研究引起一種用於中和烯烴低聚合(較佳為烯烴二聚合)催化系統之新穎方法的發展，該催化系統包含至少一種鹵化衍生物，該新穎方法採用使反應流出物與至少一種腈化合物接觸之步驟。 已出人意料地表明此種方法可用於有效地中和包含至少一種鹵化衍生物的用於烯烴低聚合反應之催化系統。詳言之，根據本發明之方法可用於避免形成含氯有機產物，此等產物獲自存在於催化系統中之鹵化衍生物與二聚合反應期間所形成之烯烴之間的次要反應。 本發明之中和方法的目標之一為避免形成之烯烴被源自催化系統之不可忽略量的鹵素污染，詳言之藉由形成鹵化有機產物(含氯或含溴)。此等鹵素可能尤其有害且難以從烯烴中除去，詳言之在烯烴隨後用於諸如氫甲醯化反應或氫化反應之特定反應的情況下。
本發明係關於一種用於中和烯烴低聚合(較佳為烯烴二聚合)催化系統之方法，該催化系統包含至少一種鹵化衍生物，其特徵在於使包含該催化系統之反應流出物與至少一種包含至少一種甲腈化合物-C≡N之腈化合物RC≡N接觸，R係含有1至20個碳原子之烴基，其可為飽和或不飽和、直鏈或分支鏈、環狀或芳族烴基，其可包含或可不包含雜原子。 根據本發明之方法適用於包含採用包含鹵化衍生物之催化系統由烯烴二聚合或低聚合反應產生之二聚物及低聚物的反應流出物。有利的是，該催化系統係液相形式之均相催化系統。 低聚合定義為單體單元Cn
H2n
(n=2至10)轉化成一種化合物或化合物之混合物，其通式為Cp
H2p
，其中4≤p≤80，較佳為其中4≤p≤50，更佳其中4≤p≤26及更佳其中4≤p≤14。 反應流出物有利地獲自低聚合方法，較佳獲自在常壓至20 MPa範圍內、較佳0.5至8 MPa範圍內之總壓力及-40℃至+250℃範圍內、較佳-20℃至150℃範圍內之溫度下操作的烯烴二聚合方法。 作為饋料用於烯烴低聚合方法中、或較佳用於烯烴二聚合方法中之烯烴係含有2至10個碳原子之烯烴，且該等烯烴較佳係選自單獨或呈混合物形式、純或經稀釋之乙烯、丙烯、正丁烯及正戊烯；較佳地，所使用之烯烴係正丁烯、丙烯及/或乙烯。在該等烯烴經稀釋之情況下，該等烯烴經一或多種烷稀釋，該等烷諸如彼等獲自諸如催化裂解或蒸汽裂解之石油精煉法中「餾分」中所見。該等烯烴可源自非化石來源，諸如生物質。舉例而言，低聚合方法中所用之烯烴可有利地由醇產生，且詳言之，由醇之脫水產生。 烯烴低聚合之方法，較佳烯烴二聚合之方法，可在溶劑存在下操作。在此情況下，該溶劑可選自有機溶劑及環狀或非環狀之飽和、不飽和、芳族或非芳族烴。詳言之，該溶劑可選自純或呈混合物形式之己烷、環己烷、甲基環己烷、庚烷、丁烷或異丁烷、較佳為含有4至20個碳原子之單烯烴或二烯烴、苯、甲苯、鄰二甲苯、1,3,5-三甲苯、乙苯及離子液體。 根據本發明之中和方法適用於任何採用包含鹵化衍生物之催化劑的烯烴低聚合或二聚合催化系統。根據本發明之方法，較佳為均相之催化系統包含至少一種鹵化衍生物。 鹵化衍生物可為烯烴低聚合催化系統中熟習此項技術者已知的任何鹵化化合物。 鹵化衍生物有利地為鹵化烷基鋁，公式為AlR'm
X3-m
，其中R'係含有1至12個碳原子之烴基，諸如烷基、芳基、芳烷基、烷芳基或環烷基，X係氯或溴原子，X較佳為氯原子，且m係0至2範圍內數字。 較佳地，鹵化衍生物係選自單獨使用或呈混合物形式使用之倍半氯化乙基鋁(Et3
Al2
Cl3
)、二氯化甲基鋁(MeAlCl2
)、二氯化乙基鋁(EtAlCl2
)、二氯化異丁基鋁(iBuAlCl2
)及氯化二乙基鋁(Et2
AlCl)。 在一些催化系統中，鹵化烷基鋁可視情況富含公式為AlX3
之三鹵化鋁。可引用之非限制性實例如下：(例如)富含三氯化鋁且具有公式AlEt0,9
Cl2,1
之二氯化乙基鋁、(例如)富含三氯化鋁且具有公式AlBu0,9
Cl2,1
之二氯化異丁基鋁。 在該方法之一種變化形式中，催化系統可用於二相液-液介質，該介質含有一種不與或僅稍微可與含有產物之有機相混溶之具有離子性質的介質。一種此類型之催化系統描述於專利US 5 104 840 B中。在此情況下，具有離子性質之介質可包含至少一種公式為Q+
A-
之鹽，其中Q+
係四級銨或鏻陽離子或兩者之混合物或鋰陽離子，且A-
係配位或非配位陰離子，較佳為選自由以下形成之群：鹵代鋁酸鹽、有機鹵代鋁酸鹽、有機沒食子酸鹽、有機鹵代沒食子酸鹽或此等化合物中至少兩者的混合物。 除鹵化衍生物之外，催化系統還有利地包含鎳前驅體。 鎳前驅體可選自單獨使用或以混合物形式使用之呈水合形式或非水合形式之氯化鎳(II)、氯化鎳(II)(二甲氧基乙烷)、溴化鎳(II)、溴化鎳(II)(二甲氧基乙烷)、氟化鎳(II)、碘化鎳(II)、硫酸鎳(II)、碳酸鎳(II)、二甲基乙二肟鎳(II)、氫氧化鎳(II)、羥基乙酸鎳(II)、草酸鎳(II)、羧酸鎳(II) (諸如2-乙基己酸鹽)、辛酸鎳(II)、苯酚鎳(II)、乙酸鎳(II)、三氟乙酸鎳(II)、三氟甲磺酸鎳(II)、乙醯基丙酮酸鎳(II)、六氟乙醯基丙酮酸鎳(II)、氯化烯丙基鎳(II)、溴化烯丙基鎳(II)、氯化甲基烯丙基鎳(II)二聚物、六氟磷酸烯丙基鎳(II)、六氟磷酸甲基烯丙基鎳(II)、雙環戊二烯基鎳(II)、雙烯丙基鎳(II)及雙甲基烯丙基鎳(II)。該等鎳前驅體可視情況與路易斯鹼錯合。 在烯烴低聚合方法、較佳烯烴二聚合方法出口處，反應流出物可包含未經轉化之烯烴、諸如1-丁烯、1-己烯、1-辛烯之α-烯烴及其他C4至C10反應產物以及任何反應溶劑。該流出物亦包含用於反應之催化系統的至少一部分。 根據本發明，烯烴低聚合反應，較佳烯烴二聚合反應中之流出物有利地與包含至少一個甲腈基-C≡N之腈化合物RC≡N接觸，R係含有1至20個碳原子之烴基，其可為飽和或不飽和、直鏈或分支鏈、環狀或芳族烴基，可包含或可不包含雜原子。較佳地，烴基R含有1至15個碳原子，更佳地含有1至10個碳原子。雜原子係選自硫、氧、氮及磷。 反應流出物(包括包含鹵化衍生物之催化系統)與腈化合物之間的接觸可直接於烯烴低聚合反應出口處進行。當低聚合在含有離子性質之介質的二相液-液介質中進行時，含有低聚物之有機相較佳在反應流出物與腈化合物接觸之前藉由傾析與離子液相分離。 較佳地，腈化合物係選自乙腈、丙腈、丁腈(butanenitrile或butyronitrile)、己腈、環己腈、丙烯腈、苄腈及環戊烷甲腈。更佳地，腈化合物係選自乙腈、丙腈、丁腈。更佳地，腈化合物係乙腈。 本發明之中和方法採用一定量的足以實質上除去催化系統中所有鹵素的腈化合物。較佳地，腈化合物與鹵化衍生物之間的莫耳比在1至30範圍內，較佳在1至15範圍內，且更佳在1至10範圍內。 有利的是，烯烴低聚合反應，較佳烯烴二聚合反應之流出物與腈化合物之間的接觸在-20℃至100℃範圍內之溫度下進行。有利的是，中和溫度為已進行烯烴低聚合反應，尤其烯烴二聚合反應之溫度。 由此藉由本發明之中和方法來中和之流出物可視情況隨後經氫氧化鈉或水或酸處理，接著進行分餾。實例
以下實例說明本發明，但不限制其範疇。實例 1 ： 流出物不經腈化合物處理 ( 非根據本發明 )
將100 mL獲自丁烯二聚合(稱為粗烯(dimate))之辛烯餾分引入到以乾燥氮氣淨化之圓筒中。接下來，依次引入(相對於dimate)0.043重量%辛酸鎳(II)及(相對於dimate)0.18重量%二氯化乙基鋁(EtAlCl2
=EADC)。催化系統具有莫耳比Al/Ni=15且包含經EADC引入的1000 ppm氯。此橙色溶液在50℃下在攪拌下(2000 rpm) 加熱5分鐘。 利用注射器將50 mL加熱至50℃之20%氫氧化鈉水溶液在攪拌下引入至此溶液。攪拌保持5分鐘隨後停止。傾析有機相及水相，隨後水相用套管萃取。將50 mL經預加熱至50℃的水添加至有機相。全部攪拌5分鐘(2000 rpm )。各相立即沈澱。其澄清且無色。進行另外兩次水洗滌。水相被除去。有機相(dimate)藉由氣相層析(GC)及X射線螢光(XRF)分析以分析氯。實例 2 ： 利用乙腈處理流出物 ， 乙腈 /EADC 莫耳比為 2.5( 根據本發明 )
將100 mL獲自丁烯二聚合(稱為dimate)之辛烯餾分引入到以乾燥氮氣淨化之圓筒中。接下來，依次引入(相對於dimate)0.043重量%辛酸鎳(II)，及(相對於dimate)0.18重量%二氯化乙基鋁(EtAlCl2
=EADC)。催化系統具有莫耳比Al/Ni=15且包含經EADC引入的1000 ppm氯。此橙色溶液在50℃下在攪拌下(2000 rpm) 加熱5分鐘。 隨後利用注射器注入由VWR銷售商標為LiPerSolv Chromanorm含有30 ppm H2
O的乙腈(CH3
CN)(商用分析級，99.9%)，乙腈/EADC莫耳比為2.5。攪拌5分鐘。形成發白的沈澱物。隨後引入氫氧化鈉，如前所述。當氫氧化鈉引入時沈澱消失。隨後步驟與描述於實例1中之以水洗滌兩次一致。各相立即沈澱。實例 3 ： 利用乙腈處理流出物 ， 乙腈 /EADC 莫耳比為 5( 根據本發明 )
此實例如實例2所述進行，除了乙腈/EADC莫耳比為5。實例 4 ： 利用乙腈處理流出物 ， 乙腈 /EADC 莫耳比為 5( 根據本發明 )
此實例如實例3所述進行，除了利用由Grosseron銷售商標為PanReac含有0.1重量% H2
O的乙腈CH3
CN(商用分析級，99.7%)。實例 5: 利用乙腈處理流出物 ， 乙腈 /EADC 莫耳比為 10( 根據本發明 )
此實例如實例4所述進行，除了乙腈/EADC莫耳比為10。 表1報告獲自GC及XRF對不經處理之流出物(實例1)及利用本發明之中和方法處理之流出物分析的結果。表 1 : 流出物之分析 
*量測值的不確定度 使用本發明之乙腈中和方法處理後氯含量比不經處理所得小的多。
Claims (8)
- 一種包含中和來自烯烴低聚合之催化系統的方法，該催化系統包含至少一種鹵化衍生物，該鹵化衍生物係公式為AlR'mX3-m之鹵化烷基鋁，其中R'係含有1至12個碳原子之烴基，X係氯或溴原子且m係大於0至2之範圍內的數字，該中和係藉由使來自該烯烴低聚合且包含該催化系統之反應流出物與至少一種包含至少一種甲腈化合物-C≡N之腈化合物RC≡N接觸，R係含有1至20個碳原子之烴基，其為飽和或不飽和、直鏈或分支鏈、環狀或芳族烴基，且其視情況包含雜原子，其中該腈化合物與該鹵化衍生物之間的莫耳比(腈化合物/鹵化衍生物)係1至30，其中該催化系統由於該接觸而被中和且獲得經中和的流出物。
- 如請求項1之方法，其中該烴基R含有1至15個碳原子。
- 如請求項1或2之方法，其中該腈化合物係乙腈、丙腈、丁腈(butanenitrile或butyronitrile)、己腈、環己腈、丙烯腈、苄腈或環戊烷甲腈。
- 如請求項1或2之方法，其包含使來自該烯烴低聚合之該反應流出物與該至少一種腈化合物在-20℃至100℃之溫度下接觸。
- 如請求項1或2之方法，其中該烯烴低聚合係烯烴二聚合之方法。
- 如請求項1或2之方法，其中該鹵化衍生物係單獨使用之或以混合物形式使用之倍半氯化乙基鋁(Et3Al2Cl3)、二氯化甲基鋁(MeAlCl2)、二氯化乙基鋁(EtAlCl2)、二氯化異丁基鋁(iBuAlCl2)或氯化二乙基鋁(Et2AlCl)。
- 如請求項1或2之方法，其中用於該烯烴低聚合之烯烴係含有2至10個碳原子的烯烴。
- 如請求項1或2之方法，其進一步包含以水、氫氧化鈉或酸處理該經中和的流出物，接著進行分餾。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1663138 | 2016-12-22 | ||
| ??1663138 | 2016-12-22 | ||
| FR1663138A FR3061175B1 (fr) | 2016-12-22 | 2016-12-22 | Procede de neutralisation d'un systeme catalytique de dimerisation d'olefines contenant au moins un derive halogene. |
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| TW201840517A TW201840517A (zh) | 2018-11-16 |
| TWI756324B true TWI756324B (zh) | 2022-03-01 |
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| TW106144313A TWI756324B (zh) | 2016-12-22 | 2017-12-18 | 用於中和包含至少一種鹵化衍生物之烯烴二聚合催化系統之方法 |
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| US (1) | US10662133B2 (zh) |
| EP (1) | EP3339273A1 (zh) |
| CN (1) | CN108218660A (zh) |
| AR (1) | AR110555A1 (zh) |
| FR (1) | FR3061175B1 (zh) |
| TW (1) | TWI756324B (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR3103486A1 (fr) | 2019-11-26 | 2021-05-28 | IFP Energies Nouvelles | Procede de neutralisation d’une composition catalytique contenu dans un effluent issu d’une etape d’oligomerisation |
| FR3103485B1 (fr) * | 2019-11-26 | 2023-03-24 | Ifp Energies Now | Procédé de séparation d’un effluent issu d’une étape d’oligomérisation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4401559A (en) * | 1981-04-21 | 1983-08-30 | Institut Francais Du Petrole | Process for removing halogenated impurities from olefin oligomers |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL290631A (zh) | 1962-11-30 | 1900-01-01 | ||
| FR1410430A (fr) | 1963-08-10 | 1965-09-10 | Studiengesellschaft Kohle Mbh | Procédé pour l'oligomérisation et la polymérisation d'oléfines et catalyseurs pour ces opérations |
| US3485881A (en) | 1967-10-09 | 1969-12-23 | Phillips Petroleum Co | Dimerization of olefins |
| FR2114114A5 (en) | 1970-11-10 | 1972-06-30 | Inst Francais Du Petrole | Olefin dimerisation catalyst - contg halogen deactivated by ammonia or amine |
| FR2443877A1 (fr) * | 1978-12-11 | 1980-07-11 | Inst Francais Du Petrole | Nouvelle composition catalytique et sa mise en oeuvre pour l'oligomerisation des olefines |
| FR2563214B1 (fr) | 1984-04-20 | 1986-06-27 | Inst Francais Du Petrole | Procede pour l'elimination du nickel, de l'aluminium et du chlore des oligomeres d'olefines |
| FR2659871B1 (fr) | 1990-03-20 | 1992-06-05 | Inst Francais Du Petrole | Composition liquide non aqueuse a caractere ionique et son utilisation comme solvant. invention de mm. yves chauvin, dominique commereuc, isabelle guibard, andre hirschauer, helene olivier, lucien saussine. |
| BE1007698A3 (fr) * | 1993-11-04 | 1995-10-03 | Solvay | Systeme catalytique utilisable pour la polymerisation des alpha-olefines et procede pour cette polymerisation. |
| CA2255908A1 (en) * | 1996-05-30 | 1997-12-04 | Phillips Petroleum Company | Process for removing nitrile in etherification process |
| EP1754694A1 (en) * | 2005-08-10 | 2007-02-21 | Linde AG | Method for deactivation and removal of catalytic components in the oligomerisation of ethylene |
| US9169169B2 (en) * | 2006-03-10 | 2015-10-27 | Exxonmobil Chemical Patents Inc. | Lowering nitrogen-containing Lewis bases in molecular sieve oligomerisation |
| MY156865A (en) * | 2008-01-30 | 2016-04-15 | Linde Ag | Method for preparing linear alpha-olefins |
| 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 |
-
2016
- 2016-12-22 FR FR1663138A patent/FR3061175B1/fr not_active Expired - Fee Related
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2017
- 2017-12-18 TW TW106144313A patent/TWI756324B/zh active
- 2017-12-18 EP EP17306799.2A patent/EP3339273A1/fr not_active Withdrawn
- 2017-12-19 AR ARP170103586A patent/AR110555A1/es unknown
- 2017-12-21 CN CN201711393525.6A patent/CN108218660A/zh active Pending
- 2017-12-21 US US15/850,622 patent/US10662133B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4401559A (en) * | 1981-04-21 | 1983-08-30 | Institut Francais Du Petrole | Process for removing halogenated impurities from olefin oligomers |
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| Publication number | Publication date |
|---|---|
| CN108218660A (zh) | 2018-06-29 |
| TW201840517A (zh) | 2018-11-16 |
| US10662133B2 (en) | 2020-05-26 |
| US20180179127A1 (en) | 2018-06-28 |
| FR3061175A1 (fr) | 2018-06-29 |
| EP3339273A1 (fr) | 2018-06-27 |
| AR110555A1 (es) | 2019-04-10 |
| FR3061175B1 (fr) | 2020-07-31 |
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