DE2542230C2 - Verfahren zur Herstellung eines Phosphor enthaltenden Katalysators aus einem kristallinen Aluminosilicatzeolithen - Google Patents
Verfahren zur Herstellung eines Phosphor enthaltenden Katalysators aus einem kristallinen AluminosilicatzeolithenInfo
- Publication number
- DE2542230C2 DE2542230C2 DE2542230A DE2542230A DE2542230C2 DE 2542230 C2 DE2542230 C2 DE 2542230C2 DE 2542230 A DE2542230 A DE 2542230A DE 2542230 A DE2542230 A DE 2542230A DE 2542230 C2 DE2542230 C2 DE 2542230C2
- Authority
- DE
- Germany
- Prior art keywords
- phosphorus
- zeolite
- catalyst
- weight
- zeolites
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000010457 zeolite Substances 0.000 title claims description 185
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 160
- 239000011574 phosphorus Substances 0.000 title claims description 158
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 title claims description 154
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 150
- 229910021536 Zeolite Inorganic materials 0.000 title claims description 142
- 239000003054 catalyst Substances 0.000 title claims description 86
- 238000000034 method Methods 0.000 title claims description 19
- 229910000323 aluminium silicate Inorganic materials 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 36
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052725 zinc Inorganic materials 0.000 claims description 22
- 239000011701 zinc Substances 0.000 claims description 22
- -1 phosphorus compound Chemical class 0.000 claims description 19
- 150000001336 alkenes Chemical class 0.000 claims description 18
- 239000000377 silicon dioxide Substances 0.000 claims description 18
- 238000005804 alkylation reaction Methods 0.000 claims description 16
- 230000029936 alkylation Effects 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 150000003751 zinc Chemical class 0.000 claims description 12
- 150000001768 cations Chemical group 0.000 claims description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 56
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 230000002378 acidificating effect Effects 0.000 description 20
- 229930195733 hydrocarbon Natural products 0.000 description 18
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 10
- 235000012239 silicon dioxide Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000002168 alkylating agent Substances 0.000 description 9
- 229940100198 alkylating agent Drugs 0.000 description 9
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000012808 vapor phase Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 6
- 239000012022 methylating agents Substances 0.000 description 6
- 230000011987 methylation Effects 0.000 description 6
- 238000007069 methylation reaction Methods 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000005899 aromatization reaction Methods 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
- 238000001354 calcination Methods 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
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- 229940102396 methyl bromide Drugs 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 2
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- 230000009471 action Effects 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- LBPGAOJVQOCVLO-UHFFFAOYSA-N benzene ethylbenzene toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1.CCC1=CC=CC=C1 LBPGAOJVQOCVLO-UHFFFAOYSA-N 0.000 description 1
- PNZDHKJDENGMIZ-UHFFFAOYSA-N benzene;1,2-diethylbenzene Chemical compound C1=CC=CC=C1.CCC1=CC=CC=C1CC PNZDHKJDENGMIZ-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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- BEQVQKJCLJBTKZ-UHFFFAOYSA-N diphenylphosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)C1=CC=CC=C1 BEQVQKJCLJBTKZ-UHFFFAOYSA-N 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
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- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- 239000012071 phase Substances 0.000 description 1
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- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical class PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 description 1
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- C10G35/00—Reforming naphtha
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- C10G35/095—Catalytic reforming characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves
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- B01J29/405—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
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- 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
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- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/508,308 US3972832A (en) | 1974-09-23 | 1974-09-23 | Phosphorus-containing zeolite catalyst |
| US508306A US3906054A (en) | 1974-09-23 | 1974-09-23 | Alkylation of olefins |
| US508307A US3911041A (en) | 1974-09-23 | 1974-09-23 | Conversion of methanol and dimethyl ether |
| US05/538,666 US3965208A (en) | 1975-01-06 | 1975-01-06 | Methylation of toluene |
| US05/563,286 US3962364A (en) | 1975-03-28 | 1975-03-28 | Alkylation in presence of phosphorus-modified crystalline luminosilicate catalyst |
| US05/605,968 US4002698A (en) | 1975-08-19 | 1975-08-19 | Methylation of toluene in the presence of a phosphorus-modified activated crystalline aluminosilicate catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2542230A1 DE2542230A1 (de) | 1976-04-01 |
| DE2542230C2 true DE2542230C2 (de) | 1985-01-31 |
Family
ID=27560081
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2542230A Expired DE2542230C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Herstellung eines Phosphor enthaltenden Katalysators aus einem kristallinen Aluminosilicatzeolithen |
| DE2560440A Expired DE2560440C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Herstellung von Kohlenwasserstoffen |
| DE2560442A Expired DE2560442C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Herstellung von Olefinen aus Olefinen mit kleinerer Anzahl an Kohlenstoffatomen |
| DE2560441A Expired DE2560441C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Umwandlung von Paraffinen zu einem Olefine enthaltenden Produkt |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2560440A Expired DE2560440C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Herstellung von Kohlenwasserstoffen |
| DE2560442A Expired DE2560442C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Herstellung von Olefinen aus Olefinen mit kleinerer Anzahl an Kohlenstoffatomen |
| DE2560441A Expired DE2560441C2 (de) | 1974-09-23 | 1975-09-22 | Verfahren zur Umwandlung von Paraffinen zu einem Olefine enthaltenden Produkt |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5815443B2 (2) |
| DD (1) | DD123446A5 (2) |
| DE (4) | DE2542230C2 (2) |
| FR (1) | FR2285176A1 (2) |
| GB (1) | GB1496181A (2) |
| IT (1) | IT1042752B (2) |
| NL (1) | NL7511167A (2) |
| NZ (1) | NZ178543A (2) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ183608A (en) * | 1976-03-31 | 1978-12-18 | Mobil Oil Corp | Aluminosilicate zeolite catalyst for selectine production of para-diakyl substituted benzenes |
| US4060568A (en) * | 1976-03-31 | 1977-11-29 | Mobil Oil Corporation | Silica-modified zeolite catalyst and conversion therewith |
| US4283306A (en) * | 1979-04-20 | 1981-08-11 | E. I. Du Pont De Nemours And Company | Crystalline silica and use in alkylation of aromatics |
| JPS5643123U (2) * | 1979-09-12 | 1981-04-20 | ||
| US4274982A (en) * | 1979-10-12 | 1981-06-23 | Mobil Oil Corporation | Method for maintaining para-selectivity of modified zeolite catalyst |
| EP0040015B1 (en) * | 1980-05-13 | 1986-06-11 | Imperial Chemical Industries Plc | Process for making olefins |
| US4310440A (en) * | 1980-07-07 | 1982-01-12 | Union Carbide Corporation | Crystalline metallophosphate compositions |
| US4423269A (en) * | 1981-09-25 | 1983-12-27 | Chevron Research Company | Oligomerization of gaseous olefins |
| US4417088A (en) * | 1981-09-25 | 1983-11-22 | Chevron Research Company | Oligomerization of liquid olefins |
| US4511746A (en) * | 1981-09-25 | 1985-04-16 | Chevron Research Company | Low activity catalyst oligomerization process |
| US4431527A (en) * | 1981-11-13 | 1984-02-14 | Standard Oil Company (Indiana) | Process for hydrogen treating high nitrogen content hydrocarbon feeds |
| US4454241A (en) * | 1982-05-24 | 1984-06-12 | Exxon Research And Engineering Co. | Phosphorus-containing catalyst |
| US4440871A (en) * | 1982-07-26 | 1984-04-03 | Union Carbide Corporation | Crystalline silicoaluminophosphates |
| US4576805A (en) * | 1982-08-27 | 1986-03-18 | Mobil Oil Corporation | Increasing lattice metal content of porous inorganic crystalline compositions |
| JPS6042220A (ja) * | 1983-08-15 | 1985-03-06 | モビル オイル コ−ポレ−シヨン | ゼオライト処理法 |
| JPS60103020A (ja) * | 1983-11-08 | 1985-06-07 | Agency Of Ind Science & Technol | 結晶性アルミノホスホシリケ−トおよびそれを触媒として用いる炭化水素の製造方法 |
| US4668837A (en) * | 1983-11-21 | 1987-05-26 | The Dow Chemical Company | Phosphorus modified magnesium silicate |
| JPS60114042A (ja) * | 1983-11-25 | 1985-06-20 | Matsushita Electric Works Ltd | 電力線搬送システム |
| EP0176150B2 (en) * | 1984-09-25 | 1994-02-02 | Catalysts & Chemicals Industries Co., Ltd. | Catalytic cracking, process for heavy oil |
| JPS61126041A (ja) * | 1984-11-22 | 1986-06-13 | Res Assoc Util Of Light Oil | ベンゼンのエチル化法 |
| US4960504A (en) * | 1984-12-18 | 1990-10-02 | Uop | Dewaxing catalysts and processes employing silicoaluminophosphate molecular sieves |
| JPS61221137A (ja) * | 1985-03-28 | 1986-10-01 | Teijin Yuka Kk | P−キシレンの製造法 |
| AU5645686A (en) * | 1985-06-05 | 1986-12-18 | Mobil Oil Corp. | Cracking with molecular sieves containing aluminium, phosphorous and silicon |
| US4665251A (en) * | 1985-06-12 | 1987-05-12 | Mobil Oil Corporation | Aromatization reactions with zeolites containing phosphorus oxide |
| IN167718B (2) * | 1985-06-28 | 1990-12-08 | Chevron Res | |
| JPS6263528A (ja) * | 1985-09-17 | 1987-03-20 | Teijin Yuka Kk | P−キシレンの製造法 |
| JPS6450827A (en) * | 1987-08-20 | 1989-02-27 | Agency Ind Science Techn | Production of lower olefin |
| JPH04316524A (ja) * | 1991-04-12 | 1992-11-06 | Nippon Oil Co Ltd | アルキルビフエニル類の製造方法 |
| IT1250435B (it) * | 1991-07-01 | 1995-04-07 | Mini Ricerca Scient Tecnolog | Catalizzatore per l'alchilazione di composti aromatici e processo impiegante lo stesso |
| ES2076068B1 (es) * | 1993-03-17 | 1996-06-16 | Consejo Superior Investigacion | Procedimiento de preparacion de catalizadores a base de zeolitas tratadas con acido fosforico, utiles para su aplicacion en unidades de craqueo catalitico. |
| US5925586A (en) * | 1996-12-31 | 1999-07-20 | Exxon Chemical Patents, Inc. | Phosphorus modified small pore molecular sieve catalysts, and their use in the production of light olefins |
| US6613951B1 (en) * | 1999-09-23 | 2003-09-02 | Mobil Oil Corporation | Process for converting methanol to olefins |
| US7038100B2 (en) * | 2001-04-30 | 2006-05-02 | Exxonmobil Chemical Patents, Inc. | Aromatics alkylation |
| CN1257769C (zh) * | 2003-10-31 | 2006-05-31 | 中国石油化工股份有限公司 | 一种含磷和金属组分的mfi结构分子筛及其应用 |
| RU2399414C2 (ru) * | 2005-10-07 | 2010-09-20 | ЭсКей ЭНЕРДЖИ КО., ЛТД. | Гидротермически стабильный микропористый молекулярно-ситовый катализатор и метод его изготовления |
| JP4823655B2 (ja) * | 2005-11-21 | 2011-11-24 | 出光興産株式会社 | キシレン類の製造方法 |
| JP5094506B2 (ja) * | 2008-03-28 | 2012-12-12 | 出光興産株式会社 | 軽質オレフィンの製造方法 |
| US8115041B2 (en) * | 2008-04-02 | 2012-02-14 | Saudi Basic Industries Corporation | Pretreatment of a phosphorus-modified zeolite catalyst for an aromatic alkylation process |
| US8252967B2 (en) * | 2009-04-14 | 2012-08-28 | Exxonmobil Chemical Patents Inc. | Process for the purification of paraxylene |
| FI124814B (fi) | 2010-10-18 | 2015-01-30 | Lappeenrannan Teknillinen Yliopisto | Sähkökoneen staattori ja sähkökone |
| JP5798821B2 (ja) | 2011-07-15 | 2015-10-21 | 三菱重工業株式会社 | メタノールからガソリンを製造するともに発電する方法およびシステム |
| JP5812781B2 (ja) | 2011-09-21 | 2015-11-17 | 三菱重工業株式会社 | メタノールからガソリンと水素を製造する方法および装置 |
| CN104114277B (zh) * | 2011-10-17 | 2017-02-15 | 埃克森美孚研究工程公司 | 磷改性沸石催化剂 |
| EP3433223A4 (en) * | 2016-03-25 | 2019-12-25 | ExxonMobil Chemical Patents Inc. | CATALYST AND PROCESS FOR PRODUCING PARAXYLENE |
| CN114375288B (zh) * | 2019-09-30 | 2024-08-23 | 陶氏环球技术有限责任公司 | 醚化方法 |
| JP7737397B2 (ja) * | 2020-04-13 | 2025-09-10 | 中国石油化工股▲ふん▼有限公司 | リン改質mfi構造分子篩、リン改質mfi構造分子篩を含む接触分解助剤および接触分解触媒、ならびにその調製方法 |
| CN117920324A (zh) * | 2022-10-24 | 2024-04-26 | 中国石油化工股份有限公司 | 含磷zsm-5分子筛及其制备方法和应用 |
| CN116477638B (zh) * | 2023-03-23 | 2024-08-16 | 延长中科(大连)能源科技股份有限公司 | 一种高稳定性丝光沸石分子筛的制备方法及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647682A (en) | 1968-10-23 | 1972-03-07 | Union Carbide Corp | Olefin production by the catalytic treatment of hydrocarbons |
| US3702886A (en) * | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
| US3709979A (en) * | 1970-04-23 | 1973-01-09 | Mobil Oil Corp | Crystalline zeolite zsm-11 |
| GB1403329A (en) * | 1972-04-28 | 1975-08-28 | Mobil Oil Corp | Vapour-phase alkylation in presence of crystalline alumino silicate catalyst |
| US3751504A (en) * | 1972-05-12 | 1973-08-07 | Mobil Oil Corp | Vapor-phase alkylation in presence of crystalline aluminosilicate catalyst with separate transalkylation |
| CS191916B2 (en) | 1973-08-09 | 1979-07-31 | Mobil Oil Corp | Method of producing aromatic hydrocarbons |
-
1975
- 1975-09-01 NZ NZ178543A patent/NZ178543A/xx unknown
- 1975-09-11 GB GB37415/75A patent/GB1496181A/en not_active Expired
- 1975-09-19 FR FR7528734A patent/FR2285176A1/fr active Granted
- 1975-09-22 DE DE2542230A patent/DE2542230C2/de not_active Expired
- 1975-09-22 NL NL7511167A patent/NL7511167A/xx not_active Application Discontinuation
- 1975-09-22 DE DE2560440A patent/DE2560440C2/de not_active Expired
- 1975-09-22 IT IT27498/75A patent/IT1042752B/it active
- 1975-09-22 DE DE2560442A patent/DE2560442C2/de not_active Expired
- 1975-09-22 DE DE2560441A patent/DE2560441C2/de not_active Expired
- 1975-09-23 DD DD188505A patent/DD123446A5/xx unknown
- 1975-09-23 JP JP50114397A patent/JPS5815443B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5157688A (en) | 1976-05-20 |
| FR2285176B1 (2) | 1982-10-01 |
| FR2285176A1 (fr) | 1976-04-16 |
| DE2560441C2 (de) | 1986-05-22 |
| JPS5815443B2 (ja) | 1983-03-25 |
| DE2560440C2 (de) | 1986-11-13 |
| IT1042752B (it) | 1980-01-30 |
| NL7511167A (nl) | 1976-03-25 |
| DE2542230A1 (de) | 1976-04-01 |
| DD123446A5 (2) | 1976-12-20 |
| NZ178543A (en) | 1978-04-03 |
| GB1496181A (en) | 1977-12-30 |
| DE2560442C2 (de) | 1986-10-16 |
| DE2560441A1 (2) | 1982-08-26 |
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