JP5036972B2 - アルキル化芳香族組成物の製造方法 - Google Patents
アルキル化芳香族組成物の製造方法 Download PDFInfo
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- JP5036972B2 JP5036972B2 JP2005071798A JP2005071798A JP5036972B2 JP 5036972 B2 JP5036972 B2 JP 5036972B2 JP 2005071798 A JP2005071798 A JP 2005071798A JP 2005071798 A JP2005071798 A JP 2005071798A JP 5036972 B2 JP5036972 B2 JP 5036972B2
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- angstroms
- zeolite catalyst
- alkylated aromatic
- catalyst
- olefin
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 111
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 237
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 237
- 239000010457 zeolite Substances 0.000 claims abstract description 237
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 229
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 83
- 238000000034 method Methods 0.000 claims abstract description 80
- 229910052680 mordenite Inorganic materials 0.000 claims abstract description 23
- 230000008569 process Effects 0.000 claims abstract description 17
- 239000011148 porous material Substances 0.000 claims description 160
- 150000001336 alkenes Chemical class 0.000 claims description 103
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 95
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 80
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 74
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 73
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 58
- 230000029936 alkylation Effects 0.000 claims description 50
- 239000000377 silicon dioxide Substances 0.000 claims description 36
- 239000004711 α-olefin Substances 0.000 claims description 31
- 230000001186 cumulative effect Effects 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000011230 binding agent Substances 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 229910000287 alkaline earth metal oxide Inorganic materials 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
- 238000011010 flushing procedure Methods 0.000 claims description 2
- 230000009849 deactivation Effects 0.000 abstract description 14
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- 239000000047 product Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 28
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000002131 composite material Substances 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 19
- -1 aluminum halide Chemical class 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 11
- 229910052753 mercury Inorganic materials 0.000 description 11
- 150000004996 alkyl benzenes Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- 238000006317 isomerization reaction Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
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- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
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- 238000006116 polymerization reaction Methods 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 4
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002594 sorbent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011164 primary particle 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
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000012690 zeolite precursor Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/90—Regeneration or reactivation
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/647—2-50 nm
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/651—50-500 nm
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/66—Pore distribution
-
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Description
(a)Y型ゼオライトからなり、ピーク孔径が、ASTM試験第D4284−03による測定値として約2000オングストローム以下であり、そして約500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り約0.30ミリリットル以下である大細孔構造を持つアルキル化触媒の存在下に、アルキル化反応を行なって得られたアルキル化芳香族炭化水素アルキル化生成物、および
(b)シリカとアルミナとのモル比が約50:1乃至約105:1の範囲にあるモルデナイト型ゼオライトからなり、ピーク孔径が、ASTM試験第D4284−03による測定値として約900オングストローム以下であり、そして約500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り約0.30ミリリットル以下である大細孔構造を持つアルキル化触媒の存在下に、アルキル化反応を行なって得られたアルキル化芳香族炭化水素アルキル化生成物。
(a)Y型ゼオライトからなり、ピーク孔径が、ASTM試験第D4284−03による測定値として約2000オングストローム以下であり、そして約500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り約0.30ミリリットル以下である大細孔構造を持つゼオライト触媒を存在させて、少なくとも一種の芳香族炭化水素を、アルキル化条件下で少なくとも一種のオレフィンと接触させて、第一のアルキル化芳香族炭化水素生成物を生成させる工程、
(b)シリカとアルミナとのモル比が約50:1乃至約105:1の範囲にあるモルデナイト型ゼオライトからなり、ピーク孔径が、ASTM試験第D4284−03による測定値として約900オングストローム以下であり、そして約500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り約0.30ミリリットル以下である大細孔構造を持つゼオライト触媒を存在させて、少なくとも一種の芳香族炭化水素を、アルキル化条件下で少なくとも一種のオレフィンと接触させて、第二のアルキル化芳香族炭化水素生成物を生成させる工程、そして
(c)第一のアルキル化芳香族炭化水素生成物と第二のアルキル化芳香族炭化水素生成物を混ぜ合わせて、アルキル化芳香族組成物を形成する工程、
ただし、(a)工程と(b)工程は任意の順序で行うことができる。
(a)Y型ゼオライト、および
(b)シリカとアルミナとのモル比が約50:1乃至約105:1の範囲にあるモルデナイト型ゼオライト、
からなり、そしてピーク孔径が、ASTM試験第D4284−03による測定値として約2000オングストローム未満であり、約500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り約0.30ミリリットル以下である大細孔構造を持つゼオライト触媒組成物に関する。
「アルキレート」は、アルキル化芳香族炭化水素を意味する。
異性化工程は、バッチ式または連続式で実施することができる。工程温度は50℃乃至250℃の範囲であってよい。バッチ式では、一般的な方法は撹拌下にあるオートクレーブまたはガラス製フラスコを使用することであり、所望の反応温度に加熱してもよい。連続法は、固定床法で最も効率良く行われる。固定床法の空間速度は、0.1乃至10又はもっと高い時間当り重量の空間速度範囲とすることができる。
ノルマルアルファオレフィン、部分分枝鎖異性化オレフィンおよび分枝鎖オレフィンによる芳香族炭化水素のアルキル化は、当該分野の熟練者には知られている任意の方法で実施することができる。
アルキル化炭化水素のスルホン化は、当該分野の熟練者に公知の任意の方法により実施することができる。
アルキル芳香族スルホン酸の炭酸塩化・過塩基性化は、当該分野の熟練者には公知の任意の方法により実施することができ、アルキル芳香族スルホネートが生成する。
一旦モルデナイト型ゼオライト触媒及び触媒複合体が完全に失活すると、オレフィンが重合によってゼオライト材料の活性部位を含む結晶微細孔から外に拡散することができない大分子種になるために、アルキル化反応は停止する。しかし、失活したモルデナイト型ゼオライト触媒及び触媒複合体を取り除くために、反応器床を交換する必要はない。アルキル化実施の最後に反応器へのオレフィン供給流を止めて、芳香族炭化水素流を充分な時間、一般には約12時間乃至約24時間反応器に通してフラッシュし続けるようにすることによって、失活したモルデナイト型ゼオライト触媒及び触媒複合体を再活性化する。
ゼオリスト・インターナショナル社またはその他任意の商業源より入手したY型ゼオライト粉末とモルデナイト型ゼオライト粉末を混合することにより、ゼオライト触媒組成物1を製造する。Y型ゼオライトとモルデナイト型ゼオライトの粉末を、所望とするアルキル化芳香族生成物に基づいて任意の割合で混合する。
ゼオリスト・インターナショナル社より入手したY型ゼオライト、CBV760(商品名)を用いて、上記実施例1に記載したようにしてY型ゼオライト触媒複合体を製造した。
ゼオリスト・インターナショナル社より入手したモルデナイト型ゼオライト、CBV90A(商品名)を用いて、上記実施例1に記載したようにしてモルデナイト型ゼオライト触媒複合体を製造した。
実施例2及び3で製造したY型ゼオライト触媒複合体とモルデナイト型ゼオライト触媒複合体とを混合することにより、ゼオライト触媒組成物を製造する。Y型ゼオライト触媒複合体とモルデナイト型ゼオライト触媒複合体を、所望のアルキル化芳香族生成物に基づいて任意の割合で混合する。一例として、Y型ゼオライト触媒複合体をモルデナイト型ゼオライト触媒複合体と混合して、ゼオライト触媒組成物2において最終比85:15を得る。
一般に、ノルマルアルファオレフィン、部分分枝鎖異性化オレフィンおよび分枝鎖オレフィンによる芳香族炭化水素のアルキル化を以下に記載するようにして実施した:
一般に、ノルマルアルファオレフィン、部分分枝鎖異性化オレフィンおよび分枝鎖オレフィンによる芳香族炭化水素のアルキル化を以下に記載するようにして実施した:
上記実施例5及び6におけるようにY型ゼオライト触媒を用いて製造したアルキル化ベンゼン85重量%とモルデナイト型ゼオライトを用いて製造したアルキル化ベンゼン15重量%との混合物を、下記の条件を用いて、チューブ状反応器(長さ2メートル、内径1センチメートル)内に三酸化硫黄(SO3)と空気を順流で同時に流すことによりスルホン化した。
加熱及び冷却能力を備え、300から350rpmの間で回転するステンレス鋼製機械撹拌器、撹拌翼の真上に位置するCO2添加用のガス導入管(内径2ミリメートル)、窒素ガス下にある蒸留カラムと冷却器を備えた5リットル四つ口ガラス製反応器に、収集物129.4グラムを入れた。
Claims (35)
- 下記の工程からなるアルキル化芳香族組成物の製造方法:
(a)Y型ゼオライトからなり、ピーク孔径が、ASTM試験第D4284−03による測定値として2000オングストローム以下であり、そして500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り0.30ミリリットル以下である大細孔構造を持つゼオライト触媒の存在下に、少なくとも一種の芳香族炭化水素を、アルキル化条件下にて少なくとも一種のオレフィンと接触させて、第一のアルキル化芳香族炭化水素生成物を生成させる工程、
(b)シリカとアルミナとのモル比が50:1乃至105:1の範囲にあるモルデナイト型ゼオライトからなり、ピーク孔径が、ASTM試験第D4284−03による測定値として900オングストローム以下であり、そして500オングストローム以下の孔径の細孔の累積孔容積が、ASTM試験第D4284−03による測定値としてグラム当り0.30ミリリットル以下である大細孔構造を持つゼオライト触媒の存在下に、少なくとも一種の芳香族炭化水素を、アルキル化条件下にて少なくとも一種のオレフィンと接触させて、第二のアルキル化芳香族炭化水素生成物を生成させる工程、そして
(c)第一のアルキル化芳香族炭化水素生成物と第二のアルキル化芳香族炭化水素生成物を混ぜ合わせて、アルキル化芳香族組成物を形成する工程、
ただし、(a)工程と(b)工程は任意の順序で行うことができる。 - (b)工程が更に、失活したゼオライト触媒を、芳香族炭化水素でフラッシュして再活性化する工程を含む請求項1に記載の方法。
- さらに、アルキル化芳香族組成物をスルホン化してアルキル化芳香族スルホン酸を生成させる工程を含む請求項2に記載の方法。
- さらに、アルキル化芳香族スルホン酸をアルカリ土類金属および二酸化炭素と反応させて、炭酸塩化した過塩基性アルキル化芳香族スルホネートを生成させる工程を含む請求項3に記載の方法。
- アルキル化芳香族組成物中の第一のアルキル化芳香族炭化水素生成物が、全アルキル化芳香族組成物に対して40%乃至99%の範囲にある請求項2に記載の方法。
- アルキル化芳香族組成物中の第一のアルキル化芳香族炭化水素生成物が、全アルキル化芳香族組成物に対して50%乃至90%の範囲にある請求項5に記載の方法。
- アルキル化芳香族組成物中の第一のアルキル化芳香族炭化水素生成物が、全アルキル化芳香族組成物に対して70%乃至80%の範囲にある請求項6に記載の方法。
- (a)工程および(b)工程において、オレフィンが、独立に、アルファオレフィン、異性化オレフィン、分枝鎖オレフィンまたはそれらの混合物である請求項2に記載の方法。
- アルファオレフィンまたは異性化オレフィンが炭素原子6個乃至40個を有する請求項8に記載の方法。
- アルファオレフィンまたは異性化オレフィンが炭素原子20個乃至40個を有する請求項9に記載の方法。
- 分枝鎖オレフィンが炭素原子6個乃至70個を有する請求項8に記載の方法。
- 分枝鎖オレフィンが炭素原子8個乃至50個を有する請求項11に記載の方法。
- 分枝鎖オレフィンが炭素原子12個乃至18個を有する請求項12に記載の方法。
- (a)工程または(b)工程において、オレフィンが、独立に、炭素原子6個乃至40個を持つ部分的に分枝鎖を有する異性化オレフィンである請求項2に記載の方法。
- 部分的に分枝鎖を有する異性化オレフィンが炭素原子20個乃至40個を有する請求項14に記載の方法。
- (a)工程および(b)工程において、芳香族炭化水素が、独立に、トルエンまたはベンゼンである請求項2に記載の方法。
- (a)及び(b)工程において、ゼオライト触媒の400オングストローム以下の孔径の細孔の累積孔容積が、グラム当り0.30ミリリットル以下である請求項2に記載の方法。
- (a)及び(b)工程において、ゼオライト触媒の300オングストローム以下の孔径の細孔の累積孔容積が、グラム当り0.25ミリリットル以下である請求項17に記載の方法。
- (a)及び(b)工程において、ゼオライト触媒の300オングストローム以下の孔径の細孔の累積孔容積が、グラム当り0.20ミリリットル以下である請求項18に記載の方法。
- (a)及び(b)工程において、ゼオライト触媒の400オングストローム以下の孔径の細孔の累積孔容積が、グラム当り0.05ミリリットル乃至0.18ミリリットルの範囲にある請求項19に記載の方法。
- (a)及び(b)工程において、ゼオライト触媒の300オングストローム以下の孔径の細孔の累積孔容積が、グラム当り0.08ミリリットル乃至0.16ミリリットルの範囲にある請求項20に記載の方法。
- (a)工程において、Y型ゼオライト触媒のピーク孔径が、700オングストローム乃至1800オングストロームの範囲にある請求項2に記載の方法。
- (a)工程において、Y型ゼオライト触媒のピーク孔径が、750オングストローム乃至1600オングストロームの範囲にある請求項22に記載の方法。
- (a)工程において、Y型ゼオライト触媒のピーク孔径が、800オングストローム乃至1400オングストロームの範囲にある請求項23に記載の方法。
- (b)工程において、モルデナイト型ゼオライト触媒のピーク孔径が、400オングストローム乃至800オングストロームの範囲にある請求項2に記載の方法。
- (b)工程において、モルデナイト型ゼオライト触媒のピーク孔径が、400オングストローム乃至700オングストロームの範囲にある請求項25に記載の方法。
- (b)工程において、モルデナイト型ゼオライト触媒のピーク孔径が、450オングストローム乃至600オングストロームの範囲にある請求項26に記載の方法。
- (a)工程において、Y型ゼオライト触媒のシリカとアルミナとの比が、5:1乃至100:1の範囲にある請求項2に記載の方法。
- (a)工程において、Y型ゼオライト触媒のシリカとアルミナとの比が、30:1乃至90:1の範囲にある請求項28に記載の方法。
- (a)工程において、Y型ゼオライト触媒のシリカとアルミナとの比が、60:1乃至80:1の範囲にある請求項29に記載の方法。
- (b)工程において、モルデナイト型ゼオライト触媒のシリカとアルミナとの比が、50:1乃至105:1の範囲にある請求項2に記載の方法。
- (b)工程において、モルデナイト型ゼオライト触媒のシリカとアルミナとの比が、60:1乃至80:1の範囲にある請求項31に記載の方法。
- (a)工程のY型ゼオライトおよび(b)工程のモルデナイト型ゼオライトが結合剤を含んでいる請求項2に記載の方法。
- (a)工程のY型ゼオライトの結合剤および(b)工程のモルデナイト型ゼオライトの結合剤がアルミナである請求項33に記載の方法。
- (a)工程のY型ゼオライトおよび(b)工程のモルデナイト型ゼオライトがタブレットの形状にある請求項2に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/799907 | 2004-03-12 | ||
US10/799,907 US6977319B2 (en) | 2004-03-12 | 2004-03-12 | Alkylated aromatic compositions, zeolite catalyst compositions and processes for making the same |
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Cited By (1)
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JP2012012404A (ja) * | 2004-03-12 | 2012-01-19 | Chevron Oronite Co Llc | アルキル化芳香族組成物、ゼオライト触媒組成物及びその製造方法 |
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EP1574251A3 (en) | 2005-12-28 |
JP2012012404A (ja) | 2012-01-19 |
US7183452B2 (en) | 2007-02-27 |
EP1574251A2 (en) | 2005-09-14 |
US6977319B2 (en) | 2005-12-20 |
SG115737A1 (en) | 2005-10-28 |
CA2496363A1 (en) | 2005-09-12 |
US7109141B2 (en) | 2006-09-19 |
US20060142625A1 (en) | 2006-06-29 |
US20060142626A1 (en) | 2006-06-29 |
US20060036119A1 (en) | 2006-02-16 |
JP2005255682A (ja) | 2005-09-22 |
CA2496363C (en) | 2013-09-10 |
EP1574251B1 (en) | 2011-03-23 |
US7563938B2 (en) | 2009-07-21 |
US20050202954A1 (en) | 2005-09-15 |
JP5475731B2 (ja) | 2014-04-16 |
DE602005027015D1 (de) | 2011-05-05 |
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