JP5995974B2 - 芳香族炭化水素をトランスアルキル化する方法 - Google Patents
芳香族炭化水素をトランスアルキル化する方法 Download PDFInfo
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- JP5995974B2 JP5995974B2 JP2014530675A JP2014530675A JP5995974B2 JP 5995974 B2 JP5995974 B2 JP 5995974B2 JP 2014530675 A JP2014530675 A JP 2014530675A JP 2014530675 A JP2014530675 A JP 2014530675A JP 5995974 B2 JP5995974 B2 JP 5995974B2
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- Prior art keywords
- benzene
- transalkylation
- catalyst
- purity
- conditions
- 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.)
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- 238000000034 method Methods 0.000 title claims description 69
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 328
- 238000010555 transalkylation reaction Methods 0.000 claims description 93
- 239000003054 catalyst Substances 0.000 claims description 85
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 50
- 239000000047 product Substances 0.000 claims description 41
- 239000010457 zeolite Substances 0.000 claims description 31
- 229910052751 metal Inorganic materials 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 29
- 229910021536 Zeolite Inorganic materials 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 23
- 229930195733 hydrocarbon Natural products 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims description 22
- 239000008096 xylene Substances 0.000 claims description 21
- 239000007795 chemical reaction product Substances 0.000 claims description 19
- 150000003738 xylenes Chemical class 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
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- 150000001491 aromatic compounds Chemical class 0.000 description 15
- -1 C9 + aromatics Chemical class 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000002808 molecular sieve Substances 0.000 description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 10
- 230000009849 deactivation Effects 0.000 description 9
- 229910052680 mordenite Inorganic materials 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
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- 230000000694 effects Effects 0.000 description 8
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- 239000000203 mixture Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 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
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- 229910052759 nickel Inorganic materials 0.000 description 3
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- 238000011282 treatment Methods 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 238000001833 catalytic reforming Methods 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 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
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- PJHPFAFEJNBIDC-UHFFFAOYSA-N 1-(4-bromophenyl)piperazine Chemical compound C1=CC(Br)=CC=C1N1CCNCC1 PJHPFAFEJNBIDC-UHFFFAOYSA-N 0.000 description 1
- YQZBFMJOASEONC-UHFFFAOYSA-N 1-Methyl-2-propylbenzene Chemical class CCCC1=CC=CC=C1C YQZBFMJOASEONC-UHFFFAOYSA-N 0.000 description 1
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical class CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical class CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- DMUVQFCRCMDZPW-UHFFFAOYSA-N 1-ethyl-2-propylbenzene Chemical class CCCC1=CC=CC=C1CC DMUVQFCRCMDZPW-UHFFFAOYSA-N 0.000 description 1
- GKRIOFBXFFLIAJ-UHFFFAOYSA-N 2,3-dimethylpentane;3-methylhexane Chemical compound CCCC(C)CC.CCC(C)C(C)C GKRIOFBXFFLIAJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 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
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 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
- 238000013459 approach Methods 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
- 229910001680 bayerite Inorganic materials 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- ISUUFJFPSXCANV-UHFFFAOYSA-N cyclohexane;methylcyclopentane Chemical compound CC1CCCC1.C1CCCCC1 ISUUFJFPSXCANV-UHFFFAOYSA-N 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 150000005195 diethylbenzenes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000005194 ethylbenzenes Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910001679 gibbsite Inorganic materials 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming 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
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
- C07C2529/26—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
[0002]本発明は、概して芳香族炭化水素化合物をトランスアルキル化するための改良された方法に関する。より詳しくは、本発明はキシレン類及びベンゼンを製造する芳香族トランスアルキル化プロセスに関する。
・圧力:10〜500kPa;
・水素/炭化水素モル比:0.05〜0.5。
Mm n+Rr p+Al1−xSiyOz
(式中、Mは少なくとも1種類の交換可能なカチオンであり、リチウム、ナトリウム、カリウム、ルビジウム、セシウム、カルシウム、ストロンチウム、バリウム、及びこれらの混合物など(しかしながらこれらに限定されない)のアルカリ及びアルカリ土類金属からなる群から選択される)
によって表される実験組成式を有する。Rは、プロトン化アミン、プロトン化ジアミン、第4級アンモニウムイオン、ジ第4級アンモニウムイオン、プロトン化アルカノールアミン、及び4級化アルカノールアンモニウムイオンからなる群から選択される少なくとも1種類の有機カチオンである。この成分に関し、「m」はAlに対するMのモル比であり、0.05〜0.95の範囲であり;「r」はAlに対するRのモル比であり、0.05〜0.95の値を有し;「n」はMの加重平均価数であり、1〜2の値を有し;「p」はRの加重平均価数であり、1〜2の値を有し;「y」はAlに対するSiのモル比であり、3〜50の範囲であり;「z」はAlに対するOのモル比であり、等式:
z=(m・n+r・p+3+4y)/2
によって定められる値を有する。
[0043]米国特許7,626,064B1に記載されている手順にしたがって触媒を製造し、標準的なトランスアルキル化試験手順にしたがって芳香族化合物のトランスアルキル化に関して試験した。試験の前に、触媒を当該技術において周知なようにその場で硫化して、か焼触媒のMoO3を少なくとも部分的に硫化モリブデンに転化させた。試験への供給材料は、芳香族化合物を重量基準で実質的に以下の割合:
トルエン:50%;
C9芳香族化合物:38%;
C10芳香族化合物:10%;
C11+芳香族化合物:1.5%;
で含んでいた。
[0044]試験を制御して、触媒1gあたり1時間あたり3.0gのHCBN供給材料の重量毎時空間速度において供給材料の50重量%の一定の転化レベルを維持した。試験は、触媒1ポンドあたり5バレルの供給材料の触媒寿命を超えて行い、供給材料の転化実験の初期段階(0〜0.7)及び最終段階(5+)において標準的なトランスアルキル化条件を加えた。下表において、「BPP」は触媒1ポンドあたり、而して運転サイクルにおける期間あたりに処理される供給材料のバレル数を示し、「0」はサイクルの開始時である。「温度」はその運転期間に関する加重平均床温度(℃)である。「圧力」は運転圧力(MPa)である。「H2/HC」は供給材料の炭化水素に対する水素のモル比である。「純度」は再循環水素中のH2のモル%である。「DAR」は50%の転化レベルを維持するのに必要なBPPあたりの失活速度(℃)である。生成物のベンゼンの純度は、「ベンゼン%」として示す。重量毎時空間速度はサイクルを通して3に維持した。
Claims (7)
- (a)芳香族炭化水素化合物を含む供給流を、MOR骨格タイプを有するアルミノシリケートゼオライト成分、無機酸化物バインダー、及び金属成分を含む触媒を含むトランスアルキル化区域に導入し;
(b)供給材料の導入から触媒を再生または交換するためにプロセスを停止するまでをプロセスサイクルとするとき、プロセスサイクルの初めから50%以下の部分中において、供給流を、トランスアルキル化区域内で、ベンゼンの純度を指向するトランスアルキル化条件下において触媒と接触させ;
(c)プロセスサイクルの50%超から後段の部分において、供給流を、トランスアルキル化区域内で標準的なトランスアルキル化条件下において触媒と接触させ;そして
(d)キシレン類及び高純度のベンゼンフラクションを含む反応生成物流を生成させる;
ことを含み、
標準的なトランスアルキル化条件とは、200〜540℃かつ100kPa〜6MPa(絶対圧)の条件であり、ベンゼンの純度を指向するトランスアルキル化条件は、標準的なトランスアルキル化条件と比べてより高い運転温度、より低い運転圧力、及びより低い水素/炭化水素比となる条件である、
異なるトランスアルキル化条件下のサイクルの2以上の部分を含むプロセスサイクル中において、ベンゼン生成物の純度を維持しながら芳香族炭化水素化合物をトランスアルキル化する方法。 - 触媒が1種類以上の更なるアルミノシリケートゼオライト成分を更に含む、請求項1に記載の方法。
- 1種類以上の更なるアルミノシリケートゼオライト成分がMFIを含む、請求項2に記載の方法。
- 金属成分が、モリブデン、スズ、ゲルマニウム、インジウム、レニウム、白金、パラジウム、及びこれらの組み合わせからなる群から選択される金属を含む、請求項1に記載の方法。
- 高純度のベンゼンフラクションが重量基準で少なくとも99.9%のベンゼンを含む、請求項1に記載の方法。
- 反応生成物流を分離して重量基準で少なくとも99.9%のベンゼンを含むベンゼン生成物流を生成させることを更に含む、請求項1に記載の方法。
- プロセスサイクルの初めから25%以下の間にベンゼンの純度を指向する条件を適用する、請求項1に記載の方法。
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PCT/US2012/051784 WO2013039656A2 (en) | 2011-09-14 | 2012-08-22 | Process for transalkylating aromatic hydrocarbons |
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US20140100403A1 (en) * | 2012-10-05 | 2014-04-10 | Uop Llc | Low pressure transalkylation process |
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US10781149B2 (en) * | 2014-12-19 | 2020-09-22 | Exxonmobil Chemical Patents Inc. | Transalkylation process |
JP7185625B2 (ja) * | 2016-10-10 | 2022-12-07 | エクソンモービル ケミカル パテンツ インコーポレイテッド | 重質芳香族化合物のbtxへの転化プロセス及び使用する触媒組成物 |
MY192461A (en) * | 2016-12-08 | 2022-08-22 | Shell Int Research | Process for preparing a molybdenum-platinum-based catalyst for the synthesis of benzene by transalkylation |
US11229899B2 (en) | 2016-12-09 | 2022-01-25 | Shell Oil Company | Catalyst composition |
RU2753341C2 (ru) * | 2017-01-25 | 2021-08-13 | Эксонмобил Кемикэл Пейтентс Инк. | Способ трансалкилирования и применяющаяся в нем каталитическая композиция |
US11103859B2 (en) * | 2020-01-06 | 2021-08-31 | Uop Llc | UZM-54 and transalkylation process using same |
CN114436755A (zh) * | 2020-10-19 | 2022-05-06 | 中国石油化工股份有限公司 | 一种芳烃烷基转移反应原料的优化方法、芳烃烷基转移反应方法与装置 |
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