JP5456466B2 - アルキル芳香族炭化水素の非常に選択的な水素化脱アルキル化のための触媒組成物 - Google Patents
アルキル芳香族炭化水素の非常に選択的な水素化脱アルキル化のための触媒組成物 Download PDFInfo
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- JP5456466B2 JP5456466B2 JP2009522186A JP2009522186A JP5456466B2 JP 5456466 B2 JP5456466 B2 JP 5456466B2 JP 2009522186 A JP2009522186 A JP 2009522186A JP 2009522186 A JP2009522186 A JP 2009522186A JP 5456466 B2 JP5456466 B2 JP 5456466B2
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- Prior art keywords
- catalyst
- hydrodealkylation
- range
- zsm
- zeolite
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims description 67
- 239000000203 mixture Substances 0.000 title claims description 30
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 title description 18
- 238000000034 method Methods 0.000 claims description 66
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 230000008569 process Effects 0.000 claims description 45
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 44
- 239000010457 zeolite Substances 0.000 claims description 31
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 29
- 229910021536 Zeolite Inorganic materials 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 229910052697 platinum Inorganic materials 0.000 claims description 24
- 229930195733 hydrocarbon Natural products 0.000 claims description 22
- 238000005470 impregnation Methods 0.000 claims description 21
- 239000008096 xylene Substances 0.000 claims description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 230000003197 catalytic effect Effects 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 229910052750 molybdenum Inorganic materials 0.000 claims description 15
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
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- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000197 pyrolysis Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical group CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
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- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 claims 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 claims 1
- BAMWORSGQSUNSC-UHFFFAOYSA-N 1-ethyl-2,3,4-trimethylbenzene Chemical compound CCC1=CC=C(C)C(C)=C1C BAMWORSGQSUNSC-UHFFFAOYSA-N 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- NZFVWAOONXJZIQ-UHFFFAOYSA-N heptan-4-ylbenzene Chemical compound CCCC(CCC)C1=CC=CC=C1 NZFVWAOONXJZIQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002751 molybdenum Chemical class 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
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- 238000006317 isomerization reaction Methods 0.000 description 18
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 13
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- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000020335 dealkylation Effects 0.000 description 10
- 238000006900 dealkylation reaction Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 239000007864 aqueous solution Substances 0.000 description 8
- 238000010555 transalkylation reaction Methods 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000007323 disproportionation reaction Methods 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 4
- 229940010552 ammonium molybdate Drugs 0.000 description 4
- 235000018660 ammonium molybdate Nutrition 0.000 description 4
- 239000011609 ammonium molybdate Substances 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
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- 230000009467 reduction Effects 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
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- YVBOZGOAVJZITM-UHFFFAOYSA-P ammonium phosphomolybdate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]P([O-])=O.[O-][Mo]([O-])(=O)=O YVBOZGOAVJZITM-UHFFFAOYSA-P 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 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
- 230000007423 decrease Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000010517 secondary reaction Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910002839 Pt-Mo Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 230000009471 action Effects 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
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- 239000011591 potassium Chemical class 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 2
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
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- 241000272168 Laridae Species 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- JUWPYOOYEVUNET-UHFFFAOYSA-N [Ir].[Re].[Pt] Chemical compound [Ir].[Re].[Pt] JUWPYOOYEVUNET-UHFFFAOYSA-N 0.000 description 1
- QCDHROIAAXHXIR-UHFFFAOYSA-N [Ni].[W].[Pt] Chemical group [Ni].[W].[Pt] QCDHROIAAXHXIR-UHFFFAOYSA-N 0.000 description 1
- WJPZDRIJJYYRAH-UHFFFAOYSA-N [Zn].[Mo] Chemical compound [Zn].[Mo] WJPZDRIJJYYRAH-UHFFFAOYSA-N 0.000 description 1
- UCYXRZPFJJBQDL-UHFFFAOYSA-N acetic acid;molybdenum Chemical compound [Mo].[Mo].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O UCYXRZPFJJBQDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
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- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 1
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- CNRRZWMERIANGJ-UHFFFAOYSA-N chloro hypochlorite;molybdenum Chemical compound [Mo].ClOCl CNRRZWMERIANGJ-UHFFFAOYSA-N 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- ZBFQOIBWJITQRI-UHFFFAOYSA-H disodium;hexachloroplatinum(2-);hexahydrate Chemical compound O.O.O.O.O.O.[Na+].[Na+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Pt+4] ZBFQOIBWJITQRI-UHFFFAOYSA-H 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 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
- 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
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- ZMCCBULBRKMZTH-UHFFFAOYSA-N molybdenum platinum Chemical compound [Mo].[Pt] ZMCCBULBRKMZTH-UHFFFAOYSA-N 0.000 description 1
- LNDHQUDDOUZKQV-UHFFFAOYSA-J molybdenum tetrafluoride Chemical compound F[Mo](F)(F)F LNDHQUDDOUZKQV-UHFFFAOYSA-J 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical class [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 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
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-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
- 238000011017 operating method Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 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
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- DBJYYRBULROVQT-UHFFFAOYSA-N platinum rhenium Chemical compound [Re].[Pt] DBJYYRBULROVQT-UHFFFAOYSA-N 0.000 description 1
- ZONODCCBXBRQEZ-UHFFFAOYSA-N platinum tungsten Chemical compound [W].[Pt] ZONODCCBXBRQEZ-UHFFFAOYSA-N 0.000 description 1
- KGRJUMGAEQQVFK-UHFFFAOYSA-L platinum(2+);dibromide Chemical compound Br[Pt]Br KGRJUMGAEQQVFK-UHFFFAOYSA-L 0.000 description 1
- ZXDJCKVQKCNWEI-UHFFFAOYSA-L platinum(2+);diiodide Chemical compound [I-].[I-].[Pt+2] ZXDJCKVQKCNWEI-UHFFFAOYSA-L 0.000 description 1
- HWLDNSXPUQTBOD-UHFFFAOYSA-N platinum-iridium alloy Chemical compound [Ir].[Pt] HWLDNSXPUQTBOD-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910001950 potassium oxide Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002468 redox effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound 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
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910021647 smectite Inorganic materials 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
- 230000001629 suppression Effects 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YPFBRNLUIFQCQL-UHFFFAOYSA-K tribromomolybdenum Chemical class Br[Mo](Br)Br YPFBRNLUIFQCQL-UHFFFAOYSA-K 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
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2006A001548 | 2006-08-03 | ||
| IT001548A ITMI20061548A1 (it) | 2006-08-03 | 2006-08-03 | Composizioni catalitiche per idrodealchilazioni altamente selettive di idrocarburi alchilaromatici |
| PCT/EP2007/006984 WO2008015027A1 (en) | 2006-08-03 | 2007-08-02 | Catalytic compositions for the highly selective hydrodealkylation of alkylaromatic hydrocarbons |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009545548A JP2009545548A (ja) | 2009-12-24 |
| JP2009545548A5 JP2009545548A5 (enExample) | 2010-09-16 |
| JP5456466B2 true JP5456466B2 (ja) | 2014-03-26 |
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| 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 |
|---|---|---|---|---|
| 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 |
| CN102781889B (zh) * | 2010-02-03 | 2015-11-25 | 埃克森美孚化学专利公司 | 重质芳族烃原料的烷基转移 |
| KR101359973B1 (ko) * | 2011-12-27 | 2014-02-12 | 주식회사 포스코 | 방향족 화합물로부터 자일렌 생산을 위한 트랜스 알킬화 촉매 |
| WO2013182534A1 (en) | 2012-06-05 | 2013-12-12 | Saudi Basic Industries Corporation | Process for producing btx from a c5-c12 hydrocarbon mixture |
| 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 |
| US10793491B2 (en) | 2014-06-13 | 2020-10-06 | Sabic Global Technologies B.V. | Process for producing benzene from C5-C12 hydrocarbon mixture |
| CN106661465B (zh) | 2014-06-13 | 2019-06-14 | Sabic环球技术有限责任公司 | 由c5-c12烃混合物生产苯的方法 |
| US10501388B2 (en) | 2015-08-21 | 2019-12-10 | Sabic Global Technologies B.V. | Process for producing BTX from a C5—C12 hydrocarbon mixture |
| EP3176243A1 (en) | 2015-12-03 | 2017-06-07 | SABIC Global Technologies B.V. | Process for preparing a hydrocracking catalyst |
| US10865348B2 (en) | 2016-07-13 | 2020-12-15 | Sabic Global Technologies B.V. | Process which does simultaneous dehydrochlorination and hydrocracking of pyrolysis oils from mixed plastic pyrolysis while achieving selective hydrodealkylation of C9+ aromatics |
| US20180019165A1 (en) | 2016-07-14 | 2018-01-18 | Entegris, Inc. | CVD Mo DEPOSITION BY USING MoOCl4 |
| EP3458190A1 (en) | 2016-08-02 | 2019-03-27 | 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 |
| CN109689842B (zh) | 2016-09-12 | 2021-01-29 | 沙特基础工业全球技术有限公司 | 加氢裂化方法 |
| CN110088244A (zh) | 2016-10-17 | 2019-08-02 | 沙特基础全球技术有限公司 | 由c5-c12烃混合物生产btx的方法 |
| WO2018104382A1 (en) * | 2016-12-08 | 2018-06-14 | Shell Internationale Research Maatschappij B.V. | Process for preparing a molybdenum-platinum-based catalyst for the synthesis of benzene by transalkylation |
| 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 |
| US11279663B2 (en) | 2017-02-16 | 2022-03-22 | 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 |
| 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 |
| US10899685B1 (en) | 2019-10-07 | 2021-01-26 | Saudi Arabian Oil Company | Catalytic hydrodearylation of heavy aromatic stream containing dissolved hydrogen |
| US11267769B2 (en) | 2019-10-07 | 2022-03-08 | Saudi Arabian Oil Company | Catalytic hydrodearylation of heavy aromatic streams containing dissolved hydrogen with fractionation |
| 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 |
| DE69031214T2 (de) * | 1989-12-13 | 1998-02-26 | Mobil Oil Corporation, New York, N.Y. | Verfahren zur katalytischen konversion einer c9+ -aromatischen charge |
| 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 PL PL07801540T patent/PL2046920T3/pl unknown
- 2007-08-02 EP EP07801540.1A patent/EP2046920B1/en active Active
- 2007-08-02 WO PCT/EP2007/006984 patent/WO2008015027A1/en not_active Ceased
- 2007-08-02 ES ES07801540.1T patent/ES2589592T3/es active Active
- 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 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 HU HUE07801540A patent/HUE030013T2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2046920T3 (pl) | 2017-03-31 |
| JP2009545548A (ja) | 2009-12-24 |
| WO2008015027A8 (en) | 2008-04-17 |
| CN101517043B (zh) | 2013-08-14 |
| US8168844B2 (en) | 2012-05-01 |
| EP2046920A1 (en) | 2009-04-15 |
| CN101517043A (zh) | 2009-08-26 |
| ITMI20061548A1 (it) | 2008-02-04 |
| US20090272672A1 (en) | 2009-11-05 |
| EA200900205A1 (ru) | 2009-08-28 |
| WO2008015027A1 (en) | 2008-02-07 |
| HUE030013T2 (hu) | 2017-04-28 |
| ES2589592T3 (es) | 2016-11-15 |
| EA016750B1 (ru) | 2012-07-30 |
| EP2046920B1 (en) | 2016-06-08 |
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