HUE030013T2 - Eljárás alkil-aromás szénhidrogének erõsen szelektív hidro-dezalkilezésére - Google Patents
Eljárás alkil-aromás szénhidrogének erõsen szelektív hidro-dezalkilezésére Download PDFInfo
- Publication number
- HUE030013T2 HUE030013T2 HUE07801540A HUE07801540A HUE030013T2 HU E030013 T2 HUE030013 T2 HU E030013T2 HU E07801540 A HUE07801540 A HU E07801540A HU E07801540 A HUE07801540 A HU E07801540A HU E030013 T2 HUE030013 T2 HU E030013T2
- Authority
- HU
- Hungary
- Prior art keywords
- catalyst
- zeolite
- platinum
- compounds
- zsm
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 58
- 230000008569 process Effects 0.000 title claims description 40
- 229930195733 hydrocarbon Natural products 0.000 title claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 17
- 239000003054 catalyst Substances 0.000 claims description 55
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 29
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 27
- 239000010457 zeolite Substances 0.000 claims description 27
- 229910021536 Zeolite Inorganic materials 0.000 claims description 25
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 22
- 229910052697 platinum Inorganic materials 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 238000005470 impregnation Methods 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- -1 triethylbenzides Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical class [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- 229910052750 molybdenum Inorganic materials 0.000 claims description 11
- 239000011733 molybdenum Substances 0.000 claims description 11
- 150000003738 xylenes Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000002739 metals Chemical class 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 238000005899 aromatization reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 150000005195 diethylbenzenes Chemical class 0.000 claims description 2
- 229910052622 kaolinite Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 238000000197 pyrolysis Methods 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 238000004230 steam cracking Methods 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- BAMWORSGQSUNSC-UHFFFAOYSA-N 1-ethyl-2,3,4-trimethylbenzene Chemical class CCC1=CC=C(C)C(C)=C1C BAMWORSGQSUNSC-UHFFFAOYSA-N 0.000 claims 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- 239000011435 rock Substances 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- 150000005199 trimethylbenzenes Chemical class 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 230000003197 catalytic effect Effects 0.000 description 21
- 238000006317 isomerization reaction Methods 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000010517 secondary reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical class CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000010555 transalkylation reaction Methods 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical class CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- ZYSWYTKKWSXNIV-UHFFFAOYSA-N N,N'-dichloroethane-1,2-diamine platinum(2+) Chemical compound [Pt+2].ClNCCNCl ZYSWYTKKWSXNIV-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000139306 Platt Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910002839 Pt-Mo Inorganic materials 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FXCWJOMEAGKNSP-UHFFFAOYSA-K [Cl-].[Cl-].[Cl-].Cl.[K+].[Pt+2] Chemical compound [Cl-].[Cl-].[Cl-].Cl.[K+].[Pt+2] FXCWJOMEAGKNSP-UHFFFAOYSA-K 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 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
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical class C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZGHDMISTQPRNRG-UHFFFAOYSA-N dimolybdenum Chemical compound [Mo]#[Mo] ZGHDMISTQPRNRG-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 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
- PCLURTMBFDTLSK-UHFFFAOYSA-N nickel platinum Chemical compound [Ni].[Pt] PCLURTMBFDTLSK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- ZONODCCBXBRQEZ-UHFFFAOYSA-N platinum tungsten Chemical compound [W].[Pt] ZONODCCBXBRQEZ-UHFFFAOYSA-N 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- ZXDJCKVQKCNWEI-UHFFFAOYSA-L platinum(2+);diiodide Chemical compound [I-].[I-].[Pt+2] ZXDJCKVQKCNWEI-UHFFFAOYSA-L 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229910052572 stoneware Inorganic materials 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
- C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
- C10G47/10—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used with catalysts deposited on a carrier
- C10G47/12—Inorganic carriers
- C10G47/16—Crystalline alumino-silicate carriers
- C10G47/18—Crystalline alumino-silicate carriers the catalyst containing platinum group metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1096—Aromatics or polyaromatics
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4018—Spatial velocity, e.g. LHSV, WHSV
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001548A ITMI20061548A1 (it) | 2006-08-03 | 2006-08-03 | Composizioni catalitiche per idrodealchilazioni altamente selettive di idrocarburi alchilaromatici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE030013T2 true HUE030013T2 (hu) | 2017-04-28 |
Family
ID=37993637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE07801540A HUE030013T2 (hu) | 2006-08-03 | 2007-08-02 | Eljárás alkil-aromás szénhidrogének erõsen szelektív hidro-dezalkilezésére |
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| Country | Link |
|---|---|
| US (1) | US8168844B2 (enExample) |
| EP (1) | EP2046920B1 (enExample) |
| JP (1) | JP5456466B2 (enExample) |
| CN (1) | CN101517043B (enExample) |
| EA (1) | EA016750B1 (enExample) |
| ES (1) | ES2589592T3 (enExample) |
| HU (1) | HUE030013T2 (enExample) |
| IT (1) | ITMI20061548A1 (enExample) |
| PL (1) | PL2046920T3 (enExample) |
| WO (1) | WO2008015027A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US9174892B2 (en) | 2010-01-19 | 2015-11-03 | Uop Llc | Process for increasing a mole ratio of methyl to phenyl |
| US8598395B2 (en) * | 2010-01-19 | 2013-12-03 | Uop Llc | Process for increasing a mole ratio of methyl to phenyl |
| SG191570A1 (en) * | 2010-02-03 | 2013-07-31 | Exxonmobil Chem Patents Inc | Transalkylation of heavy aromatic hydrocarbon feedstocks |
| KR101359973B1 (ko) * | 2011-12-27 | 2014-02-12 | 주식회사 포스코 | 방향족 화합물로부터 자일렌 생산을 위한 트랜스 알킬화 촉매 |
| CN104395436B (zh) * | 2012-06-05 | 2016-10-05 | 沙特基础工业公司 | 由c5-c12烃混合物生产btx的方法 |
| CN103657708A (zh) * | 2012-09-07 | 2014-03-26 | 中国石油天然气集团公司 | 一种用于催化汽油芳构化改质的催化剂 |
| SG11201609049VA (en) | 2014-06-13 | 2016-12-29 | Sabic Global Technologies Bv | Process for producing benzene from a c5-c12 hydrocarbon mixture |
| EP3155072B1 (en) | 2014-06-13 | 2020-05-27 | SABIC Global Technologies B.V. | Process for producing benzene from a c5-c12 hydrocarbon mixture |
| CN107922292A (zh) | 2015-08-21 | 2018-04-17 | 沙特基础工业全球技术有限公司 | 用于由c5‑c12烃混合物生产btx的方法 |
| EP3176243A1 (en) | 2015-12-03 | 2017-06-07 | SABIC Global Technologies B.V. | Process for preparing a hydrocracking catalyst |
| JP6999637B2 (ja) * | 2016-07-13 | 2022-01-18 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | 炭素数９以上の芳香族化合物類の選択的水素化脱アルキル化を達成しつつ、混合プラスチック熱分解からの熱分解油の脱塩化水素と水素化クラッキングを同時に行う方法 |
| CN109661481B (zh) | 2016-07-14 | 2021-11-30 | 恩特格里斯公司 | 使用MoOC14的CVD Mo沉积 |
| US10710058B2 (en) | 2016-08-02 | 2020-07-14 | Sabic Global Technologies B.V. | Process for preparing hydrocracking catalyst |
| US10093873B2 (en) | 2016-09-06 | 2018-10-09 | Saudi Arabian Oil Company | Process to recover gasoline and diesel from aromatic complex bottoms |
| WO2018047093A1 (en) | 2016-09-12 | 2018-03-15 | Sabic Global Technologies B.V. | Hydrocracking process |
| EA201990982A1 (ru) | 2016-10-17 | 2019-10-31 | Способ получения бтк из смеси углеводородов с5-с12 | |
| RU2757851C2 (ru) * | 2016-12-08 | 2021-10-21 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения катализатора на основе молибдена и платины для синтеза бензола путем трансалкилирования |
| US10053401B1 (en) | 2017-02-16 | 2018-08-21 | Saudi Arabian Oil Company | Process for recovery of light alkyl mono-aromatic compounds from heavy alkyl aromatic and alkyl-bridged non-condensed alkyl aromatic compounds |
| US10508066B2 (en) | 2017-02-16 | 2019-12-17 | Saudi Arabian Oil Company | Methods and systems of upgrading heavy aromatics stream to petrochemical feedstock |
| US11066344B2 (en) | 2017-02-16 | 2021-07-20 | Saudi Arabian Oil Company | Methods and systems of upgrading heavy aromatics stream to petrochemical feedstock |
| US11279663B2 (en) | 2017-02-16 | 2022-03-22 | Saudi Arabian Oil Company | Methods and systems of upgrading heavy aromatics stream to petrochemical feedstock |
| EP3834931A1 (en) * | 2018-03-14 | 2021-06-16 | Saudi Arabian Oil Company | Composite zeolite catalysts for heavy reformate conversion into xylenes |
| JP2020196685A (ja) * | 2019-06-04 | 2020-12-10 | 東ソー株式会社 | ベンゼン製造用触媒システム及びそれを用いたベンゼンの製造方法 |
| CN112237941A (zh) * | 2019-07-19 | 2021-01-19 | 国家能源投资集团有限责任公司 | 芳构化催化剂及其制备方法和低碳烯烃芳构化方法 |
| US11267769B2 (en) | 2019-10-07 | 2022-03-08 | Saudi Arabian Oil Company | Catalytic hydrodearylation of heavy aromatic streams containing dissolved hydrogen with fractionation |
| US10899685B1 (en) | 2019-10-07 | 2021-01-26 | Saudi Arabian Oil Company | Catalytic hydrodearylation of heavy aromatic stream containing dissolved hydrogen |
| CN114426456B (zh) * | 2020-10-10 | 2024-08-30 | 中国石油化工股份有限公司 | 苯与重芳烃烷基转移和甲苯甲基化的组合工艺 |
| US11613714B2 (en) | 2021-01-13 | 2023-03-28 | Saudi Arabian Oil Company | Conversion of aromatic complex bottoms to useful products in an integrated refinery process |
| JP2022127708A (ja) * | 2021-02-22 | 2022-09-01 | 東ソー株式会社 | ベンゼンの製造方法 |
| US11591526B1 (en) | 2022-01-31 | 2023-02-28 | Saudi Arabian Oil Company | Methods of operating fluid catalytic cracking processes to increase coke production |
| CN115007199A (zh) * | 2022-05-19 | 2022-09-06 | 化学与精细化工广东省实验室 | 一种碳九及以上重质芳烃加氢脱烷基催化剂及其制备方法 |
| CN117138811A (zh) * | 2022-05-23 | 2023-12-01 | 中国石油化工股份有限公司 | 加氢脱烷基催化剂及其制备方法和应用 |
| CN119680527B (zh) * | 2024-11-28 | 2025-12-16 | 甬江实验室 | 负载型碱金属氢化物作为芳烃加氢脱烷基化反应催化剂的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992468A (en) * | 1974-03-01 | 1976-11-16 | Institut Francais Du Petrole, Des Carburants Et Lubrifiants Et Entreprise De Recherches Et D'activities Petrolieres Elf | Process for the catalytic hydrodealkylation of alkylaromatic hydrocarbons |
| JPS55129232A (en) * | 1979-03-29 | 1980-10-06 | Teijin Yuka Kk | Isomerization of xylenes |
| JPS56147636A (en) * | 1980-04-17 | 1981-11-16 | Teijin Yuka Kk | Isomerization method for xylenes and its catalyst composition |
| CA1227809A (en) | 1983-10-17 | 1987-10-06 | Nancy A. Kutz | Modification of hydrocarbon conversion processes over crystalline aluminosilicate zeolite-based catalysts by incorporation of a molybdenum compound |
| US4899011A (en) * | 1986-01-15 | 1990-02-06 | Mobil Oil Corporation | Xylene isomerization process to exhaustively convert ethylbenzene and non-aromatics |
| US4899012A (en) * | 1988-10-17 | 1990-02-06 | Uop | Catalyst for the isomerization of aromatics |
| WO1991008998A1 (en) * | 1989-12-13 | 1991-06-27 | Mobil Oil Corporation | A process for the catalytic conversion of a c9+ aromatics feed |
| US5877374A (en) * | 1997-04-02 | 1999-03-02 | Chevron Chemical Company | Low pressure hydrodealkylation of ethylbenzene and xylene isomerization |
| US7148391B1 (en) * | 2002-11-14 | 2006-12-12 | Exxonmobil Chemical Patents Inc. | Heavy aromatics processing |
| ITMI20040077A1 (it) * | 2004-01-22 | 2004-04-22 | Polimeri Europa Spa | Procedimento per la idrodealchilazione catalitica di idrocarburi alchilaromatici |
| ITMI20040554A1 (it) * | 2004-03-23 | 2004-06-23 | Polimeri Europa Spa | Procedimento per la idrodealchilazione catalitica selettiva di idrocarburi alchilaromatici |
-
2006
- 2006-08-03 IT IT001548A patent/ITMI20061548A1/it unknown
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2007
- 2007-08-02 CN CN200780035892.7A patent/CN101517043B/zh active Active
- 2007-08-02 EA EA200900205A patent/EA016750B1/ru not_active IP Right Cessation
- 2007-08-02 WO PCT/EP2007/006984 patent/WO2008015027A1/en not_active Ceased
- 2007-08-02 EP EP07801540.1A patent/EP2046920B1/en active Active
- 2007-08-02 US US12/375,830 patent/US8168844B2/en active Active
- 2007-08-02 JP JP2009522186A patent/JP5456466B2/ja not_active Expired - Fee Related
- 2007-08-02 ES ES07801540.1T patent/ES2589592T3/es active Active
- 2007-08-02 HU HUE07801540A patent/HUE030013T2/hu unknown
- 2007-08-02 PL PL07801540T patent/PL2046920T3/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2589592T3 (es) | 2016-11-15 |
| ITMI20061548A1 (it) | 2008-02-04 |
| EP2046920A1 (en) | 2009-04-15 |
| JP5456466B2 (ja) | 2014-03-26 |
| CN101517043A (zh) | 2009-08-26 |
| JP2009545548A (ja) | 2009-12-24 |
| EA016750B1 (ru) | 2012-07-30 |
| EA200900205A1 (ru) | 2009-08-28 |
| US8168844B2 (en) | 2012-05-01 |
| CN101517043B (zh) | 2013-08-14 |
| WO2008015027A8 (en) | 2008-04-17 |
| US20090272672A1 (en) | 2009-11-05 |
| EP2046920B1 (en) | 2016-06-08 |
| WO2008015027A1 (en) | 2008-02-07 |
| PL2046920T3 (pl) | 2017-03-31 |
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