JP2018080130A - p−キシレンの製造方法 - Google Patents
p−キシレンの製造方法 Download PDFInfo
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- JP2018080130A JP2018080130A JP2016223197A JP2016223197A JP2018080130A JP 2018080130 A JP2018080130 A JP 2018080130A JP 2016223197 A JP2016223197 A JP 2016223197A JP 2016223197 A JP2016223197 A JP 2016223197A JP 2018080130 A JP2018080130 A JP 2018080130A
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- fraction
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- raw material
- isobutene
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 154
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 115
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 110
- 239000002994 raw material Substances 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 52
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 42
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 38
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- 229910052751 metal Inorganic materials 0.000 claims description 87
- 239000002184 metal Substances 0.000 claims description 81
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 64
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 46
- 239000001282 iso-butane Substances 0.000 claims description 32
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 19
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 19
- 238000004231 fluid catalytic cracking Methods 0.000 claims description 18
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 12
- 238000006317 isomerization reaction Methods 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 6
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- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- 239000010457 zeolite Substances 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 238000003421 catalytic decomposition reaction Methods 0.000 abstract 2
- 239000012530 fluid Substances 0.000 abstract 2
- 239000011148 porous material Substances 0.000 description 75
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 41
- 239000000047 product Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000002243 precursor Substances 0.000 description 19
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
- 239000007789 gas Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 13
- 238000010304 firing Methods 0.000 description 12
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
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- 239000006185 dispersion Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 4
- 239000001307 helium Substances 0.000 description 4
- 229910052734 helium Inorganic materials 0.000 description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
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- 150000004706 metal oxides Chemical class 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 238000000066 reactive distillation Methods 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 238000000975 co-precipitation Methods 0.000 description 3
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- 238000006297 dehydration reaction Methods 0.000 description 3
- -1 isobutane Chemical compound 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
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- WFJQGQNVERCLOQ-AATRIKPKSA-N (3e)-2,5-dimethylhexa-1,3-diene Chemical compound CC(C)\C=C\C(C)=C WFJQGQNVERCLOQ-AATRIKPKSA-N 0.000 description 2
- LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 229910020068 MgAl Inorganic materials 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IXSUHTFXKKBBJP-UHFFFAOYSA-L azanide;platinum(2+);dinitrite Chemical compound [NH2-].[NH2-].[Pt+2].[O-]N=O.[O-]N=O IXSUHTFXKKBBJP-UHFFFAOYSA-L 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
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- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 2
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- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 2
- ISZWTVCVSJVEOL-UHFFFAOYSA-N 2,5-dimethylhex-1-ene Chemical compound CC(C)CCC(C)=C ISZWTVCVSJVEOL-UHFFFAOYSA-N 0.000 description 1
- WEPNJTDVIIKRIK-UHFFFAOYSA-N 2-methylhept-2-ene Chemical compound CCCCC=C(C)C WEPNJTDVIIKRIK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000011959 amorphous silica alumina Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- TVQLLNFANZSCGY-UHFFFAOYSA-N disodium;dioxido(oxo)tin Chemical compound [Na+].[Na+].[O-][Sn]([O-])=O TVQLLNFANZSCGY-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940079864 sodium stannate Drugs 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/005—Spinels
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/24—Catalytic processes with metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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- B01J23/005—Spinels
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/626—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with tin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/08—Xylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/28—Catalytic processes with hydrides or organic compounds with ion-exchange resins
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Abstract
Description
準備工程では、重油留分の流動接触分解による生成物であって、少なくともイソブテンを含むC4留分を準備する。C4留分には、例えば、原油を蒸留して得られるC4留分、重油留分やナフサの熱分解による生成物に由来するC4留分等が含まれていてもよい。
二量化工程は、C4留分に含まれるイソブテンを原料成分として用い、当該イソブテンを含む第一の原料を二量化触媒に接触させることで、イソブテンの二量体を含むC8成分を得る工程である。第一の原料は、ガス状で二量化反応に供されてよい。
環化工程では、C8成分を含む第二の原料を脱水素触媒に接触させて、C8成分の環化脱水素反応の生成物であるp−キシレンを得る。第二の原料は、ガス状で脱水素反応に供されてよい。
・装置:日立ハイテクサイエンス製 SPS−3000型
・高周波出力:1.2kw
・プラズマガス流量:18L/min
・補助ガス流量:0.4L/min
・ネブライザーガス流量:0.4L/min
・装置:株式会社大倉理研製金属分散度測定装置R−6011
・ガス流速:30mL/分(ヘリウム、水素)
・試料量:約0.1g(小数点以下4桁目まで精秤した)
・前処理:水素気流下で400℃まで1時間かけて昇温し、400℃で60分間還元処理を行う。その後、ガスを水素からヘリウムに切り替えて400℃で30分間パージした後、ヘリウム気流下で室温まで冷却する。室温で検出器が安定するまで待った後、COパルスを行う。
・測定条件:常圧ヘリウムガス流通下、室温(27℃)で一酸化炭素を0.0929cm3ずつパルス注入し、吸着量を測定する。吸着回数は、吸着が飽和するまで行う(最低3回、最大15回)。測定された吸着量から、分散度を求める。
第一の態様に係る製造方法は、C4留分から、イソブテン及びイソブタンを含む留分(A)とノルマルブテン及びノルマルブタンを含む留分(B)とを得る第一の分離工程と、留分(A)から、イソブテンを含む留分(A−1)とイソブタンを含む留分(A−2)とを得る第二の分離工程と、を更に備えており、留分(A−1)を含む第一の原料を二量化工程で使用する。
第二の態様に係る製造方法は、C4留分から、イソブテン及びイソブタンを含む留分(A)とノルマルブテン及びノルマルブタンを含む留分(B)とを得る第一の分離工程を更に備えており、留分(A)を含む第一の原料を二量化工程で使用する。
第三の態様に係る製造方法では、イソブテン及びノルマルブテンを含む第一の原料を二量化工程で使用する。第三の態様では、イソブテン及びノルマルブテンを含むC4留分をそのまま第一の原料に利用してもよい。
<触媒A−1の調製>
担体前駆体として、0.5〜1mmに分級されたγ−アルミナ6.0g(ネオビードGB−13、(株)水澤化学工業製、1質量%の濃度で水に懸濁させた懸濁液のpH:7.9)を用意した。担体前駆体と、15.1gのMg(NO3)2・6H2Oを45mLの水に溶解させた溶液とを混合した。得られた混合液を、ロータリーエバポレーターを用いて、40℃、0.015MPaAで30分間撹拌した後、40℃、常圧で更に30分間撹拌した。その後、混合液を撹拌しながら減圧下で水を除去した。得られた固体を130℃のオーブン中で一晩乾燥させた。次に、乾燥後の固体を、空気流通下、550℃で3時間、800℃で3時間の2段階で焼成し、MgAl2O4を含む担体A−1を得た。
中東系原油を流動接触分解装置にて処理して得られたC4留分を反応蒸留装置にて分留し、塔頂からイソブタン及びイソブテン、塔底からノルマルブタン及びノルマルブテンをそれぞれ得た。塔頂ガス中のイソブタンは76質量%、イソブテンは24質量%であった。この塔頂ガスを、固定床流通式反応装置を用い、強酸性のイオン交換樹脂であるアンバーリスト35にて120℃、常圧、WHSV=50h−1の条件にて処理し、イソブタン76質量%、2,4,4−トリメチルペンテン23質量%、その他1質量%の生成物(第一の生成物)を得た。
<触媒A−2の調製>
実施例1と同じ方法で担体A−1を調製した。次いで、10.0gの担体A−1に対し、硝酸クロム水溶液(和光純薬製、[Cr(NO3)2]6H3O)を用いて、クロム担持量が約5質量%になるようクロムを含浸担持し、130℃で一晩乾燥させ、550℃で3時間焼成を行い、触媒A−2を得た。
触媒として触媒A−2を用いたこと以外は、実施例1と同様にして環化脱水素反応を行い、反応開始から9時間後の反応生成物を分析した。分析結果は表1に示すとおりであった。
<触媒A−3の調製>
γ−アルミナ6.0g(ネオビードGB−13、(株)水澤化学工業製、1質量%の濃度で水に懸濁させた懸濁液のpH:7.9)に対し、硝酸クロム水溶液(和光純薬製、[Cr(NO3)2]6H3O)を用いて、クロム担持量が約5質量%になるようクロムを含浸担持し、130℃で一晩乾燥させ、550℃で3時間焼成を行い、触媒A−3を得た。
触媒として触媒A−3を用いたこと以外は、実施例1と同様にして環化脱水素反応を行い、反応開始から9時間後の反応生成物を分析した。分析結果は表1に示すとおりであった。
Claims (12)
- 重油留分の流動接触分解による生成物であって、少なくともイソブテンを含むC4留分を準備する準備工程と、
前記イソブテンを含む第一の原料を二量化触媒に接触させて、前記イソブテンの二量体を含むC8成分を生成させる二量化工程と、
前記C8成分を含む第二の原料を脱水素触媒に接触させ、前記C8成分の環化脱水素反応によりp−キシレンを生成させる環化工程と、
を備える、p−キシレンの製造方法。 - 前記C4留分が、イソブタン、ノルマルブテン及びノルマルブタンを更に含む、請求項1に記載の製造方法。
- 前記C4留分から、前記イソブテン及び前記イソブタンを含む留分(A)と、前記ノルマルブテン及び前記ノルマルブタンを含む留分(B)と、を得る分離工程を更に備える、請求項2に記載の製造方法。
- 前記第一の原料が前記留分(A)を含む、請求項3に記載の製造方法。
- 前記留分(A)から、前記イソブテンを含む留分(A−1)と、前記イソブタンを含む留分(A−2)と、を得る第二の分離工程を更に備える、請求項3に記載の製造方法。
- 前記第一の原料が前記留分(A−1)を含む、請求項5に記載の製造方法。
- 前記留分(B)を含む第三の原料を脱水素触媒に接触させて、ブタジエンを得るブタジエン生成工程を更に備える、請求項3〜6のいずれか一項に記載の製造方法。
- 前記留分(B)を含む第三の原料を異性化触媒に接触させて、イソブテン及びイソブタンを得る異性化工程を更に備える、請求項3〜6のいずれか一項に記載の製造方法。
- 前記異性化工程で得られた前記イソブテンを前記第一の原料の一部として用いる、請求項8に記載の製造方法。
- 前記二量化触媒が、硫酸、ゼオライト、固体リン酸、フッ化水素酸、イオン液体及びイオン交換樹脂からなる群より選択される少なくとも一種の酸性触媒を含む、請求項1〜9のいずれか一項に記載の製造方法。
- 前記環化工程で用いられる前記脱水素触媒が、Al及びMgを含む無機酸化物担体と、前記無機酸化物担体に担持された活性金属と、を有する、請求項1〜10のいずれか一項に記載の製造方法。
- 前記活性金属が、Pt及びSnを含む、請求項11に記載の製造方法。
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US11066343B2 (en) | 2021-07-20 |
KR102443291B1 (ko) | 2022-09-15 |
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