CN108218660A - 使包含至少一种卤化衍生物的用于烯烃二聚的催化体系失效的方法 - Google Patents
使包含至少一种卤化衍生物的用于烯烃二聚的催化体系失效的方法 Download PDFInfo
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- CN108218660A CN108218660A CN201711393525.6A CN201711393525A CN108218660A CN 108218660 A CN108218660 A CN 108218660A CN 201711393525 A CN201711393525 A CN 201711393525A CN 108218660 A CN108218660 A CN 108218660A
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- Prior art keywords
- catalyzing
- catalyst system
- alkene
- halide derivative
- nickel
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- 150000001336 alkenes Chemical class 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 49
- 239000003054 catalyst Substances 0.000 title claims abstract description 36
- 150000004820 halides Chemical class 0.000 title claims abstract description 21
- 230000000447 dimerizing effect Effects 0.000 title claims description 10
- -1 nitrile compounds Chemical class 0.000 claims abstract description 28
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 50
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 20
- 238000006471 dimerization reaction Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 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 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000004411 aluminium Substances 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 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
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims description 2
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 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
- 239000007788 liquid 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
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 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
- XRBQEYWBWZFUIJ-UHFFFAOYSA-N 2-ethylhexanoic acid;nickel Chemical compound [Ni].CCCCC(CC)C(O)=O XRBQEYWBWZFUIJ-UHFFFAOYSA-N 0.000 description 1
- GMIHMFNPYUKMNE-UHFFFAOYSA-N 2-hydroxyacetic acid;nickel Chemical compound [Ni].OCC(O)=O GMIHMFNPYUKMNE-UHFFFAOYSA-N 0.000 description 1
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- 239000004439 Isononyl alcohol 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
- PUQISMCZEMAJKQ-UHFFFAOYSA-N N-(3-hydroxyiminobutan-2-ylidene)hydroxylamine nickel Chemical compound [Ni].CC(C(=NO)C)=NO PUQISMCZEMAJKQ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 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
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 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
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- WLKLCKQRAJOVQT-UHFFFAOYSA-N nickel penta-1,3-diene Chemical compound [Ni].C=CC=CC WLKLCKQRAJOVQT-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
- CXZRBHUCODWFTL-UHFFFAOYSA-N nickel(2+) prop-1-ene Chemical compound [Ni+2].[CH2-]C=C.[CH2-]C=C CXZRBHUCODWFTL-UHFFFAOYSA-N 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-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
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 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
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- HFUJBNCMAVYWBH-UHFFFAOYSA-N nickel;2,2,2-trifluoroacetic acid Chemical compound [Ni].OC(=O)C(F)(F)F HFUJBNCMAVYWBH-UHFFFAOYSA-N 0.000 description 1
- AIBQNUOBCRIENU-UHFFFAOYSA-N nickel;dihydrate Chemical compound O.O.[Ni] AIBQNUOBCRIENU-UHFFFAOYSA-N 0.000 description 1
- APYYCUDFPYUYEX-UHFFFAOYSA-N nickel;phenol Chemical compound [Ni].OC1=CC=CC=C1 APYYCUDFPYUYEX-UHFFFAOYSA-N 0.000 description 1
- PDXOPNHXAAQJJO-UHFFFAOYSA-N nickel;trifluoromethanesulfonic acid Chemical compound [Ni].OS(=O)(=O)C(F)(F)F PDXOPNHXAAQJJO-UHFFFAOYSA-N 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 238000005191 phase separation Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000008029 phthalate 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
- 238000010926 purge Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- 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
- C07C2/14—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
- 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
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
-
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Abstract
本发明涉及使用于烯烃低聚的催化体系失效的方法,所述催化体系包含至少一种卤化衍生物,其特征在于使反应流出物与至少一种腈类化合物接触。
Description
技术领域
本发明涉及使用于烯烃低聚、特别是烯烃二聚方法的催化体系失效的方法,所述催化体系包含至少一种卤化衍生物。
背景技术
自二十世纪五十年代以来,已经研究了使用基于与卤化活化剂(例如氯代烷基铝)缔合的过渡金属、特别是基于镍的均相催化剂的轻质烯烃的转化。这一研究导致了各种方法的开发和商业化。
作为实例,辛烯或己烯或壬烯分别通过使用来自Axens的DimersolTM方法(Revuede the Institut Français du Pétrole [Review of the French Oil Institute],第37卷,N°5,1982年9月-10月,第639页)使丁烯二聚或使丙烯低聚来生产。可以通过加氢甲酰基化反应、然后氢化成异壬醇来以良好的收率转化辛烯。这些C9醇(即含有9个碳原子)特别用于合成PVC的邻苯二甲酸酯型增塑剂。己烯或壬烯也可以用作具有非常好的辛烷值的燃料的基料。
开发能够使烯烃二聚的催化体系涉及选择过渡金属和合适的配体。在现有的催化剂体系中,已经开发了许多使用各种配体的基于镍的催化体系。可特别提及的实例是如法国专利FR 1 410 430 B中所述的π-烯丙基镍膦的卤化物与路易斯酸的配合物,如专利US 3485 881 A中所述的镍膦卤化物与路易斯酸的配合物,如法国专利FR 2 979 836 B中所述的镍与亚氨基咪唑配体的配合物以及如专利US 3 321 546 A中所述的镍的羧酸盐与烃基铝卤化物。在这样的方法中,事实证明在反应结束时使催化剂失效以防止反应以不希望的方式继续进行是必要的。
专利FR 2 114 114 B描述了用于使烯烃二聚的催化剂去活化的方法,所述催化剂含有至少一种卤化化合物,所述方法涉及使反应流出物与无水氨或胺接触。
专利US 4 642 408 B描述了处理来自在含有卤化化合物的催化剂的存在下的烯烃低聚反应的流出物的方法,其通过在第一步骤(1)中用无水氨溶液处理流出物,然后在第二步骤(2)中用碱金属水溶液洗涤流出物,条件是在步骤(1)和步骤(2)之前或之后使用氧气或含氧气体处理该流出物。
现有技术中描述的方法在失效化(neutralization)效率方面是令人满意的,但是在与使用某些抑制剂例如氨或胺有关的安全性方面引起问题,特别是因为它们在物理上是气态和/或因为它们的毒性。
本申请人的研究已经导致使用于烯烃低聚、优选用于烯烃二聚的催化体系失效的新型方法的开发,所述催化体系包含至少一种卤化衍生物,所述方法采用使反应流出物与至少一种腈类化合物接触的步骤。
已经令人意外地表明,可以使用这样的方法来有效地使用于烯烃低聚反应中的包含至少一种卤化衍生物的催化体系失效。具体而言,根据本发明的方法可以用于防止形成由存在于催化体系中的卤化衍生物与二聚反应期间形成的烯烃之间的副反应获得的含氯有机产物。
根据本发明的失效化方法的一个目的是防止形成的烯烃被源自催化体系的不可忽略的量的卤素、特别是被形成的卤化有机产物(含氯或含溴)污染。这些卤素可能是特别有害的并且难以从烯烃中除去,特别是在随后将烯烃用于特定反应、例如加氢甲酰基化反应或氢化反应的情况下。
发明内容
本发明涉及使用于烯烃低聚、优选用于烯烃二聚的催化体系失效的方法,所述催化体系包含至少一种卤化衍生物,其特征在于使包含所述催化体系的反应流出物与至少一种包含至少一个氰基-C≡N的腈类化合物RC≡N接触,R为含有1-20个碳原子的烃基,其可以是饱和或不饱和的、直链或支链的、环状或芳族的,其可以包含或不包含杂原子。
根据本发明的方法适用于包含通过烯烃的二聚或低聚反应产生的二聚体和低聚物的反应流出物,所述反应采用包含卤化衍生物的催化体系。有利地,所述催化体系是在液相中的均相催化体系。
低聚定义为将单体单元CnH2n(n = 2-10)转化为具有通式CpH2p的化合物或化合物的混合物,其中4≤p≤80,优选其中4≤p≤50,更优选其中4≤p≤26,还更优选其中4≤p≤14。
所述反应流出物有利地由烯烃的低聚方法获得,优选由烯烃的二聚方法获得,所述方法在大气压力至20MPa、优选0.5-8MPa的总压力和-40℃至+250℃、优选-20℃至150℃的温度下操作。
用作烯烃的低聚方法、或优选烯烃的二聚方法中的进料的烯烃是含有2-10个碳原子的烯烃,优选所述烯烃选自乙烯、丙烯、正丁烯和正戊烯,单独或作为混合物,纯的或被稀释的;优选地,所使用的烯烃是正丁烯、丙烯和/或乙烯。在其中所述烯烃被稀释的情况下,用一种或多种烷烃稀释所述烯烃,所述烷烃为例如在由炼油方法,例如催化裂化或蒸汽裂化获得的“馏分”中发现的那些。所述烯烃可以源自非化石来源,例如生物质。作为实例,用于低聚方法中的烯烃可以有利地由醇产生,特别是通过醇的脱水产生。
可以在溶剂的存在下操作烯烃的低聚方法、优选烯烃的二聚方法。在这样的情况下,所述溶剂可以选自有机溶剂和饱和、不饱和、芳族或非芳族烃,环状或非环状。具体而言,所述溶剂可选自己烷、环己烷、甲基环己烷、庚烷、丁烷或异丁烷、单烯烃或二烯烃,其优选含有4-20个碳原子,苯、甲苯、邻二甲苯、均三甲苯、乙苯(纯的或作为混合物)和离子液体。
根据本发明的失效化方法适用于采用包含卤化衍生物的催化剂进行烯烃低聚或二聚的任何催化体系。根据本发明的方法,所述催化体系(优选均相的)包含至少一种卤化衍生物。
所述卤化衍生物可以是本领域技术人员已知的用于烯烃低聚的催化体系中的任何卤化化合物。
有利地,所述卤化衍生物是具有式AlR’mX3-m的烷基铝卤化物,其中R’是含有1-12个碳原子的烃基,例如烷基、芳基、芳烷基、烷芳基或环烷基,X为氯原子或溴原子,X优选为氯原子,m为0-2的数。
优选地,所述卤化衍生物选自三氯化三乙基二铝(ethylaluminiumsesquichloride)(Et3Al2Cl3)、二氯化甲基铝(MeAlCl2)、二氯化乙基铝(EtAlCl2)、二氯化异丁基铝(iBuAlCl2)和氯化二乙基铝(Et2AlCl),其单独或作为混合物使用。
在一些催化体系中,所述烷基铝卤化物可以任选地富含具有式AlX3的三卤化铝。可以引用的非限制性实例如下:例如富含三氯化铝且具有式AlEt0.9Cl2.1的二氯乙基铝,例如富含三氯化铝且具有式AliBu0.9Cl2.1的二氯异丁基铝。
在所述方法的变型中,所述催化体系可用于含有具有离子性质的介质的两相液-液介质中,所述具有离子性质的介质与含有产物的有机相不混溶或与含有产物的有机相仅轻微混溶。这种类型的催化体系描述在专利US 5 104 840 B中。在这样的情况下,所述具有离子性质的介质可以包含至少一种具有式Q+A-的盐,其中Q+是季铵或鏻阳离子或两者的混合物或锂阳离子,并且A-是配位或非配位阴离子,优选选自卤化铝酸根、有机卤化铝酸根、有机镓酸根、有机卤化镓酸根或这些化合物中的至少两种的混合物。
除了所述卤化衍生物之外,所述催化体系有利地包含镍的前体。
所述镍的前体可选自氯化镍(II)、氯化镍(II)(二甲氧基乙烷)、溴化镍(II)、溴化镍(II)(二甲氧基乙烷)、氟化镍(II)、碘化镍(II)、硫酸镍(II)、碳酸镍(II)、二甲基乙二肟镍(II)、氢氧化镍(II)、羟基乙酸镍(II)、草酸镍(II)、羧酸镍(II),例如2-乙基己酸镍(II)、例如辛酸镍(II)、苯酚镍(II)、乙酸镍(II)、三氟乙酸镍(II)、三氟甲磺酸镍(II)、乙酰丙酮镍(II)、六氟乙酰丙酮镍(II)、氯化烯丙基镍(II)、溴化烯丙基镍(II)、氯化甲代烯丙基镍(II)二聚体、六氟磷酸烯丙基镍(II)、六氟磷酸甲代烯丙基镍(II)、双环戊二烯基镍(II)、双烯丙基镍(II)和双甲代烯丙基镍(II),以其水合形式或非水合形式,单独或作为混合物使用。所述镍前体可以任选地与路易斯碱配合。
在烯烃低聚方法、优选烯烃二聚方法的出口处,所述反应流出物可以包含未转化的烯烃、α-烯烃,例如1-丁烯、1-己烯、1-辛烯和其他C4-C10反应产物以及任何反应溶剂。所述流出物还包含反应中使用的催化体系的至少一部分。
有利地,根据本发明,使来自烯烃低聚反应、优选来自烯烃二聚反应的流出物与包含至少一个氰基-C≡N的腈类化合物RC≡N接触,R为含有1-20个碳原子的烃基,其可以是饱和或不饱和的、直链或支链的、环状或芳族的,其可以包含或不包含杂原子。优选地,所述烃基R含有1-15个碳原子,更优选1-10个碳原子。所述杂原子选自硫、氧、氮和磷。
反应流出物(包含含卤化衍生物的催化体系)与腈类化合物之间的接触可以直接在烯烃低聚反应的出口处进行。当在含有具有离子性质的介质的两相液-液介质中进行低聚时,在使反应流出物与腈类化合物接触之前,优选通过倾析使含有低聚物的有机相与离子液体相分离。
优选地,所述腈类化合物选自乙腈、丙腈、丁腈、己腈、环己腈、丙烯腈、苄腈和环戊腈。更优选地,所述腈类化合物选自乙腈、丙腈、丁腈。还更优选地,所述腈类化合物是乙腈。
在本发明的失效化方法中使用足以基本上除去来自催化体系的所有卤素的量的腈类化合物。优选地,所述腈类化合物和所述卤化衍生物之间的摩尔比为1-30,优选1-15,更优选1-10。
有利地,来自烯烃低聚反应、优选来自烯烃二聚反应的流出物与腈类化合物之间的接触在-20℃至100℃的温度下进行。有利地,失效化温度是进行烯烃低聚反应、特别是烯烃二聚反应的温度。
已经由此通过根据本发明的失效化方法失效的流出物然后可以任选地用氢氧化钠或用水或用酸进行处理,然后进行分馏。
具体实施方式
下面的实施例举例说明本发明而不限制其范围。
实施例1:不用腈类化合物处理流出物(不根据本发明)
将由丁烯的二聚获得的100mL的辛烯馏分(称为二聚物(dimate))引入采用干燥氮气吹扫的罐中。接着,引入0.043重量%(相对于二聚物)辛酸镍(II),然后引入0.18重量%(相对于二聚物)二氯化乙基铝(EtAlCl2=EADC)。催化体系的Al/Ni 摩尔比= 15,并且包含经由EADC引入的1000ppm的氯。将该橙色溶液在50℃下伴随搅拌(2000rpm)加热5分钟。
使用注射器将50mL的已被加热至50℃的20%氢氧化钠水溶液引入该溶液中并搅拌。搅拌保持5分钟,然后停止。倾析有机相和水相,然后用套管提取水相。将50mL的预热至50℃的水加入有机相中。全部搅拌5分钟(2000rpm)。马上使各相稳定(settled out)。它们是清澈无色的。进行另外两次水洗。除去水相。通过气相色谱(GC)和X射线荧光(XRF)分析有机相(二聚物)以分析氯。
实施例2:使用乙腈/EADC摩尔比为2.5的乙腈处理流出物(根据本发明)
将由丁烯的二聚获得的100mL的辛烯馏分(称为二聚物)引入采用干燥氮气吹扫的罐中。接着,引入0.043重量%(相对于二聚物)辛酸镍(II),然后引入0.18重量%(相对于二聚物)二氯化乙基铝(EtAlCl2=EADC)。催化体系的Al/Ni 摩尔比= 15,并且包含经由EADC引入的1000ppm的氯。将该橙色溶液在50℃下伴随搅拌(2000rpm)加热5分钟。
然后使用注射器注入由VWR销售的商标为LiPerSolv Chromanorm的含有30ppm的H2O的乙腈(CH3CN)(商业分析级,99.9%),其中乙腈/EADC摩尔比为2.5。将其搅拌5分钟。形成发白的沉淀物。然后如前文所述地引入氢氧化钠。当引入氢氧化钠时,沉淀物消失。接下来的程序与实施例1中描述的程序相同,用水洗涤两次。马上使各相稳定。
实施例3:使用乙腈/EADC摩尔比为5的乙腈处理流出物(根据本发明)
如实施例2所述进行本实施例,除了乙腈/EADC摩尔比为5。
实施例4:使用乙腈/EADC摩尔比为5的乙腈处理流出物(根据本发明)
如实施例3所述进行本实施例,除了使用由Grosseron销售的商标为PanReac的含有0.1重量%的H2O的乙腈CH3CN (商业分析级,99.7%)。
实施例5:使用乙腈/EADC摩尔比为10的乙腈处理流出物(根据本发明)
如实施例4所述进行本实施例,除了乙腈/EADC摩尔比为10。
表1报告了由未经处理的流出物(实施例1)和使用根据本发明的失效化方法处理的流出物的GC和XRF分析获得的结果。
表1:流出物的分析
*测量中的不确定性。
在使用根据本发明的乙腈失效化方法处理之后的氯的量远小于未经处理获得的氯的量。
Claims (8)
1.使用于烯烃低聚的催化体系失效的方法,所述催化体系包含至少一种卤化衍生物,所述卤化衍生物选自具有式AlR’mX3-m的烷基铝卤化物,其中R’为含有1-12个碳原子的烃基,X是氯原子或溴原子,并且m是0-2的数,其特征在于使包含所述催化体系的反应流出物与至少一种包含至少一个氰基-C≡N的腈类化合物RC≡N接触,R为含有1-20个碳原子的烃基,其可以是饱和或不饱和的、直链或支链的、环状或芳族的,其可以包含或不包含杂原子。
2.如权利要求1所述的方法,其中所述烃基R含有1-15个碳原子。
3.如权利要求1或权利要求2所述的方法,其中所述腈类化合物选自乙腈、丙腈、丁腈、己腈、环己腈、丙烯腈、苄腈和环戊腈。
4.如前述权利要求之一所述的方法,其中所述腈类化合物与所述卤化衍生物之间的摩尔比为1-30。
5.如前述权利要求之一所述的方法,其中来自烯烃低聚反应的流出物与所述腈类化合物之间的接触在-20℃至100℃的温度下进行。
6.如前述权利要求之一所述的方法,其中烯烃低聚反应是烯烃的二聚方法。
7.如前述权利要求之一所述的方法,其中所述卤化衍生物选自三氯化三乙基二铝(Et3Al2Cl3)、二氯化甲基铝(MeAlCl2)、二氯化乙基铝(EtAlCl2)、二氯化异丁基铝(iBuAlCl2)和氯化二乙基铝(Et2AlCl),其单独或作为混合物使用。
8.如前述权利要求之一所述的方法,其中用作烯烃低聚方法或烯烃二聚方法中的进料的烯烃是含有2-10个碳原子的烯烃。
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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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CN114728865A (zh) * | 2019-11-26 | 2022-07-08 | Ifp 新能源公司 | 分离获自低聚步骤的流出物的方法 |
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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 |
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US20110282092A1 (en) * | 2006-03-10 | 2011-11-17 | John Stephen Godsmark | Lowering Nitrogen-Containing Lewis Bases In Molecular Sieve Oligomerisation |
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NL286211A (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 |
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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. |
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 |
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2016
- 2016-12-22 FR FR1663138A patent/FR3061175B1/fr not_active Expired - Fee Related
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2017
- 2017-12-18 EP EP17306799.2A patent/EP3339273A1/fr not_active Withdrawn
- 2017-12-18 TW TW106144313A patent/TWI756324B/zh active
- 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
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US4401559A (en) * | 1981-04-21 | 1983-08-30 | Institut Francais Du Petrole | Process for removing halogenated impurities from olefin oligomers |
CN1106822A (zh) * | 1993-11-04 | 1995-08-16 | 索尔维公司 | 可用于α-烯烃聚合的催化体系及该聚合方法 |
CA2255908A1 (en) * | 1996-05-30 | 1997-12-04 | Phillips Petroleum Company | Process for removing nitrile in etherification process |
CN101248028A (zh) * | 2005-08-10 | 2008-08-20 | 沙特基础工业公司 | 乙烯低聚用催化组分去活化及移除的方法 |
US20110282092A1 (en) * | 2006-03-10 | 2011-11-17 | John Stephen Godsmark | Lowering Nitrogen-Containing Lewis Bases In Molecular Sieve Oligomerisation |
CN101932541A (zh) * | 2008-01-30 | 2010-12-29 | 林德股份公司 | 制备线性α-烯烃的方法 |
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CN114728865A (zh) * | 2019-11-26 | 2022-07-08 | Ifp 新能源公司 | 分离获自低聚步骤的流出物的方法 |
Also Published As
Publication number | Publication date |
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AR110555A1 (es) | 2019-04-10 |
US20180179127A1 (en) | 2018-06-28 |
FR3061175B1 (fr) | 2020-07-31 |
US10662133B2 (en) | 2020-05-26 |
TWI756324B (zh) | 2022-03-01 |
EP3339273A1 (fr) | 2018-06-27 |
FR3061175A1 (fr) | 2018-06-29 |
TW201840517A (zh) | 2018-11-16 |
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