ES2663021T3 - Transalquilación aromática usando la zeolita de aluminosilicato UZM-44 - Google Patents
Transalquilación aromática usando la zeolita de aluminosilicato UZM-44 Download PDFInfo
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- ES2663021T3 ES2663021T3 ES13863150.2T ES13863150T ES2663021T3 ES 2663021 T3 ES2663021 T3 ES 2663021T3 ES 13863150 T ES13863150 T ES 13863150T ES 2663021 T3 ES2663021 T3 ES 2663021T3
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 239000010457 zeolite Substances 0.000 title claims abstract description 60
- 229910021536 Zeolite Inorganic materials 0.000 title claims abstract description 53
- 238000010555 transalkylation reaction Methods 0.000 title claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 title description 12
- 229910000323 aluminium silicate Inorganic materials 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 35
- 239000002184 metal Substances 0.000 claims abstract description 35
- 239000002131 composite material Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 17
- 230000003197 catalytic effect Effects 0.000 claims abstract description 16
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 11
- 150000002739 metals Chemical class 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims abstract description 11
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052796 boron Inorganic materials 0.000 claims abstract description 9
- 229910052742 iron Inorganic materials 0.000 claims abstract description 9
- 230000007935 neutral effect Effects 0.000 claims abstract description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical group 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 8
- 230000000737 periodic effect Effects 0.000 claims abstract description 8
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 7
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 7
- 239000011701 zinc Substances 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 3
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 84
- 239000003054 catalyst Substances 0.000 claims description 44
- 150000001491 aromatic compounds Chemical class 0.000 claims description 31
- 239000011148 porous material Substances 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 5
- 238000005194 fractionation Methods 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 34
- 239000000377 silicon dioxide Substances 0.000 abstract description 13
- 229910052681 coesite Inorganic materials 0.000 abstract description 7
- 229910052906 cristobalite Inorganic materials 0.000 abstract description 7
- 229910052682 stishovite Inorganic materials 0.000 abstract description 7
- 229910052905 tridymite Inorganic materials 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 16
- 229910052782 aluminium Inorganic materials 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 238000005342 ion exchange Methods 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001354 calcination Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 9
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 9
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- -1 dibromide -bis (N-methylpyrrolidinium) hexane Chemical compound 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910001388 sodium aluminate Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007323 disproportionation reaction Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
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- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
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- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- YQZBFMJOASEONC-UHFFFAOYSA-N 1-Methyl-2-propylbenzene Chemical class CCCC1=CC=CC=C1C YQZBFMJOASEONC-UHFFFAOYSA-N 0.000 description 2
- CGLPXEWPIXXFDX-UHFFFAOYSA-N 1-methylpyrrolidin-1-ium;pentane;dibromide Chemical compound [Br-].[Br-].CCCCC.C[NH+]1CCCC1.C[NH+]1CCCC1 CGLPXEWPIXXFDX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
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- 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 244000130745 brown sarson Species 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
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- 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
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 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
- 230000004069 differentiation Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion 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
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229940044658 gallium nitrate Drugs 0.000 description 1
- 229910000373 gallium sulfate Inorganic materials 0.000 description 1
- SBDRYJMIQMDXRH-UHFFFAOYSA-N gallium;sulfuric acid Chemical compound [Ga].OS(O)(=O)=O SBDRYJMIQMDXRH-UHFFFAOYSA-N 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 229910001679 gibbsite Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000001198 high resolution scanning electron microscopy Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005216 hydrothermal crystallization Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- LXPCOISGJFXEJE-UHFFFAOYSA-N oxifentorex Chemical compound C=1C=CC=CC=1C[N+](C)([O-])C(C)CC1=CC=CC=C1 LXPCOISGJFXEJE-UHFFFAOYSA-N 0.000 description 1
- KZNNRLXBDAAMDZ-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane trihydrate Chemical compound O.O.O.O=[Al]O[Al]=O KZNNRLXBDAAMDZ-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012070 reactive reagent Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 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
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
- C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
- C01B39/46—Other types characterised by their X-ray diffraction pattern and their defined composition
- C01B39/48—Other types characterised by their X-ray diffraction pattern and their defined composition using at least one organic template directing agent
-
- 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
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261736347P | 2012-12-12 | 2012-12-12 | |
| US201261736347P | 2012-12-12 | ||
| US201313792667 | 2013-03-11 | ||
| US13/792,667 US8609921B1 (en) | 2012-12-12 | 2013-03-11 | Aromatic transalkylation using UZM-44 aluminosilicate zeolite |
| PCT/US2013/073462 WO2014093143A1 (en) | 2012-12-12 | 2013-12-06 | Aromatic transalkylation using uzm-44 aluminosilicate zeolite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2663021T3 true ES2663021T3 (es) | 2018-04-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13863150.2T Active ES2663021T3 (es) | 2012-12-12 | 2013-12-06 | Transalquilación aromática usando la zeolita de aluminosilicato UZM-44 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8609921B1 (enExample) |
| EP (1) | EP2931686B1 (enExample) |
| JP (1) | JP2016503430A (enExample) |
| KR (1) | KR20150066584A (enExample) |
| CN (1) | CN104870407B (enExample) |
| ES (1) | ES2663021T3 (enExample) |
| IN (1) | IN2015DN02491A (enExample) |
| RU (1) | RU2015128053A (enExample) |
| SG (1) | SG11201502366UA (enExample) |
| TW (1) | TWI508945B (enExample) |
| WO (1) | WO2014093143A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014093467A1 (en) | 2012-12-12 | 2014-06-19 | Uop Llc | Conversion of methane to aromatic compounds using a catalytic composite |
| US8921634B2 (en) | 2012-12-12 | 2014-12-30 | Uop Llc | Conversion of methane to aromatic compounds using UZM-44 aluminosilicate zeolite |
| US8912378B2 (en) | 2012-12-12 | 2014-12-16 | Uop Llc | Dehydrocyclodimerization using UZM-39 aluminosilicate zeolite |
| US8889939B2 (en) | 2012-12-12 | 2014-11-18 | Uop Llc | Dehydrocyclodimerization using UZM-44 aluminosilicate zeolite |
| US10010878B2 (en) * | 2015-03-03 | 2018-07-03 | Uop Llc | High meso-surface area, low Si/Al ratio pentasil zeolite |
| US9890094B2 (en) * | 2015-03-03 | 2018-02-13 | Uop Llc | High meso-surface area and high acid site density pentasil zeolite for use in xylene conversion |
| US20160257573A1 (en) * | 2015-03-03 | 2016-09-08 | Uop Llc | High surface area pentasil zeolite and process for making same |
| US10336665B2 (en) * | 2015-03-03 | 2019-07-02 | Uop Llc | Yields in xylene isomerization using layer MFI zeolites |
| CN107790172B (zh) * | 2016-08-30 | 2020-07-07 | 中国石油化工股份有限公司 | 烷基转移催化剂及其制备方法和用途 |
| CN107265475B (zh) * | 2017-06-19 | 2019-04-26 | 太原理工大学 | 一种铁系元素微孔分子筛和制备方法及应用 |
| US11084767B1 (en) * | 2020-02-18 | 2021-08-10 | Uop Llc | Toluene disproportionation using an enhanced UZM-44 aluminosilicate zeolite |
| US11084766B1 (en) * | 2020-02-18 | 2021-08-10 | Uop Llc | Toluene disproportionation using an enhanced UZM-39 aluminosilicate zeolite |
Family Cites Families (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB682387A (en) | 1949-06-22 | 1952-11-12 | Anglo Iranian Oil Co Ltd | Improvements relating to the removal of vanadium from petroleum products |
| NL76445C (enExample) | 1950-03-08 | |||
| US2948675A (en) | 1958-12-29 | 1960-08-09 | Sinclair Refining Co | Process for removing heavy metals from petroleum with an oil-insoluble sulfonic acid |
| NL260232A (enExample) | 1960-01-19 | |||
| US3146188A (en) | 1961-02-09 | 1964-08-25 | Sinclair Research Inc | Process for cracking a residual oil containing metallic impurities |
| US3227645A (en) | 1962-01-22 | 1966-01-04 | Chevron Res | Combined process for metal removal and hydrocracking of high boiling oils |
| US3658695A (en) | 1970-12-14 | 1972-04-25 | Phillips Petroleum Co | Production of low-metal content gas oil from topped crude oil |
| US3839187A (en) | 1971-05-17 | 1974-10-01 | Sun Oil Co | Removing metal contaminants from petroleum residual oil |
| US4052476A (en) * | 1975-04-24 | 1977-10-04 | Mobil Oil Corporation | Toluene disproportionation over zeolite catalyst |
| US4197192A (en) | 1978-10-23 | 1980-04-08 | Exxon Research & Engineering Co. | Vanadium and nickel removal from petroleum utilizing organic peroxyacid |
| US4354928A (en) | 1980-06-09 | 1982-10-19 | Mobil Oil Corporation | Supercritical selective extraction of hydrocarbons from asphaltic petroleum oils |
| US4310440A (en) | 1980-07-07 | 1982-01-12 | Union Carbide Corporation | Crystalline metallophosphate compositions |
| US4440871A (en) | 1982-07-26 | 1984-04-03 | Union Carbide Corporation | Crystalline silicoaluminophosphates |
| US4483691A (en) | 1982-09-30 | 1984-11-20 | Engelhard Corporation | Production of synthetic natural gas from coal gasification liquid by-products |
| US4478705A (en) | 1983-02-22 | 1984-10-23 | Hri, Inc. | Hydroconversion process for hydrocarbon liquids using supercritical vapor extraction of liquid fractions |
| US4735929A (en) | 1985-09-03 | 1988-04-05 | Uop Inc. | Catalytic composition for the isomerization of paraffinic hydrocarbons |
| US4645589A (en) | 1985-10-18 | 1987-02-24 | Mobil Oil Corporation | Process for removing metals from crude |
| US5961786A (en) | 1990-01-31 | 1999-10-05 | Ensyn Technologies Inc. | Apparatus for a circulating bed transport fast pyrolysis reactor system |
| US5157197A (en) | 1990-09-26 | 1992-10-20 | Catalytica, Inc. | Isoparaffin alkylation using a lewis acid promoted transition alumina catalyst |
| US5157196A (en) | 1990-12-24 | 1992-10-20 | Chemical Research & Licensing Company | Paraffin alkylation process |
| FR2754809B1 (fr) | 1996-10-21 | 2003-04-04 | Inst Francais Du Petrole | Zeolithe im-5, son procede de preparation et ses applications catalytiques |
| FR2771950B1 (fr) | 1997-12-08 | 2000-01-14 | Inst Francais Du Petrole | Procede de regeneration de catalyseurs et d'adsorbants |
| EP0999182B1 (fr) | 1998-11-02 | 2003-05-14 | Institut Francais Du Petrole | Procédé de préparation d'une zéolithe de type structural EUO à l'aide de germes de matériaux zéolitiques et son utilisation comme catalyseur d'isomérisation des aromatiques à huit atomes de carbone |
| ZA997664B (en) | 1998-12-23 | 2001-06-14 | Inst Francais Du Petrole | Euo zeolite comprising crystals and aggregates of crystals with specific granulometrys and its use as a catalyst in the isomerisation of C8 aromatic compounds. |
| US6239057B1 (en) | 1999-01-15 | 2001-05-29 | Uop Llc | Catalyst for the conversion of low carbon number aliphatic hydrocarbons to higher carbon number hydrocarbons, process for preparing the catalyst and process using the catalyst |
| FR2795405B1 (fr) * | 1999-06-22 | 2003-01-10 | Inst Francais Du Petrole | Production d'un isomere du xylene en trois etapes: separation, isomerisation avec un catalyseur a base de zeolithe euo et transalkylation avec recyclage des aromatiques en c10 |
| FR2808523B1 (fr) | 2000-05-02 | 2002-08-16 | Inst Francais Du Petrole | Procede de production conjointe ou non de monoakylaromatiques, dialkyl aromatiques et trialkyl aromatiques |
| US6613302B1 (en) | 2000-11-03 | 2003-09-02 | Uop Llc | UZM-5, UZM-5P and UZM-6: crystalline aluminosilicate zeolites and processes using the same |
| FR2837213B1 (fr) | 2002-03-15 | 2004-08-20 | Inst Francais Du Petrole | Procede de production conjointe de propylene et d'essence a partir d'une charge relativement lourde |
| KR100480229B1 (ko) | 2002-04-15 | 2005-03-30 | 한밭대학교 산학협력단 | 제올라이트 tnu-9와 tnu-10 및 그 제조방법 |
| US6776975B2 (en) | 2002-05-09 | 2004-08-17 | Uop Llc | Crystalline aluminosilicate zeolitic composition: UZM-4M |
| US7148391B1 (en) * | 2002-11-14 | 2006-12-12 | Exxonmobil Chemical Patents Inc. | Heavy aromatics processing |
| US6740788B1 (en) | 2002-12-19 | 2004-05-25 | Uop Llc | Integrated process for aromatics production |
| US7713513B2 (en) | 2003-03-21 | 2010-05-11 | Uop Llc | High silica zeolites: UZM-8HS |
| US6756030B1 (en) | 2003-03-21 | 2004-06-29 | Uop Llc | Crystalline aluminosilicate zeolitic composition: UZM-8 |
| ES2327753T3 (es) | 2004-04-14 | 2009-11-03 | Institut Francais Du Petrole | Catalizador que comprende un zaolita 10mr y una zeolita 12mr y su utilizacion en un procedimiento de transalquilacion de hidrocarburos alquilaromaticos. |
| US7615143B2 (en) | 2004-07-30 | 2009-11-10 | Exxonmobil Chemical Patents Inc. | Hydrothermally stable catalyst and its use in catalytic cracking |
| FR2877665B1 (fr) | 2004-11-09 | 2006-12-29 | Inst Francais Du Petrole | Procede de transalkylation d'hydrocarbures alkylaromatiques mis en oeuvre dans deux zones reactionnelles |
| US8134037B2 (en) | 2005-12-12 | 2012-03-13 | Uop Llc | Xylene isomerization process and apparatus |
| FR2895282B1 (fr) | 2005-12-22 | 2008-02-01 | Inst Francais Du Petrole | Catallyseur bizeolithique comprenant un metal du groupe viii et un metal du groupe iiia et son utilisation en isomerisation des composes c8 aromatiques |
| FR2895283B1 (fr) | 2005-12-22 | 2008-02-01 | Inst Francais Du Petrole | Catalyseur comprenant une zeolithe euo, une zeolithe 10mr et une zeolithe 12mr et son utilisation en isomerisation des composes c8 aromatiques |
| US20080179221A1 (en) | 2007-01-30 | 2008-07-31 | Baker Hughes Incorporated | Process for Removing Nickel and Vanadium From Hydrocarbons |
| US8398955B2 (en) | 2007-10-26 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Method of preparing a molecular sieve composition |
| US8822363B2 (en) | 2007-11-16 | 2014-09-02 | Exxonmobil Chemical Patents Inc. | Catalyst regeneration process |
| US7626064B1 (en) * | 2008-06-26 | 2009-12-01 | Uop Llc | Transalkylation process |
| US7687423B2 (en) | 2008-06-26 | 2010-03-30 | Uop Llc | Selective catalyst for aromatics conversion |
| US20100144514A1 (en) | 2008-12-09 | 2010-06-10 | Nicholas Christopher P | Process for Making Catalyst for Olefin Upgrading |
| US20100144513A1 (en) | 2008-12-09 | 2010-06-10 | Nicholas Christopher P | Catalyst for Olefin Upgrading |
| US8178740B2 (en) | 2008-12-09 | 2012-05-15 | Uop Llc | Olefin upgrading process |
| US8048403B2 (en) | 2008-12-16 | 2011-11-01 | Uop Llc | UZM-26 family of crystalline aluminosilicate compositions and method of preparing the compositions |
| US7575737B1 (en) | 2008-12-18 | 2009-08-18 | Uop Llc | UZM-27 family of crystalline aluminosilicate compositions and a method of preparing the compositions |
| CN102040459B (zh) | 2009-10-22 | 2013-09-04 | 中国石油化工股份有限公司 | 一种甲苯甲醇甲基化反应方法 |
| US8609917B2 (en) | 2010-01-19 | 2013-12-17 | Uop Llc | Process for increasing methyl to phenyl mole ratios and reducing benzene content in a motor fuel product |
| US8598395B2 (en) | 2010-01-19 | 2013-12-03 | Uop Llc | Process for increasing a mole ratio of methyl to phenyl |
| US8563795B2 (en) | 2010-01-19 | 2013-10-22 | Uop Llc | Aromatic aklylating agent and an aromatic production apparatus |
| GB2477628B (en) | 2010-02-01 | 2014-11-12 | Johnson Matthey Plc | Extruded scr filter |
| US8058496B2 (en) | 2010-03-31 | 2011-11-15 | Uop Llc | Process for xylene and ethylbenzene isomerization using UZM-35 |
| US7985886B1 (en) * | 2010-03-31 | 2011-07-26 | Uop Llc | Aromatic alkylation process using UZM-37 aluminosilicate zeolite |
| FR2959737B1 (fr) | 2010-05-06 | 2012-06-08 | Inst Francais Du Petrole | Procede de production d'alkylbenzenes ramifies utilisant une source de carbone renouvelable. |
| KR101174099B1 (ko) | 2010-05-26 | 2012-08-14 | 포항공과대학교 산학협력단 | 갈로실리케이트 제올라이트 및 그 제조 방법 |
| US20120024752A1 (en) | 2010-07-28 | 2012-02-02 | Chevron U.S.A. Inc. | Multi-Stage Hydroprocessing for the Production of High Octane Naphtha |
| US20120029257A1 (en) | 2010-07-28 | 2012-02-02 | Chevron U.S.A. Inc. | Process for the production of para-xylene |
| WO2012027034A2 (en) | 2010-08-26 | 2012-03-01 | Exxonmobil Chemical Patents Inc. | Catalyst regeneration process |
| US8460653B2 (en) | 2010-09-21 | 2013-06-11 | The Regents Of The University Of California | Superoxide dismutase variants and methods of use thereof |
| KR101249482B1 (ko) | 2011-02-10 | 2013-04-01 | 포항공과대학교 산학협력단 | 이성체화용 촉매, 그 제조 방법 및 그것을 이용한 이성체화 방법 |
| KR20110047178A (ko) | 2011-04-13 | 2011-05-06 | 포항공과대학교 산학협력단 | 티엔유-9 제올라이트를 이용한 탄화수소 전환반응 |
| KR101201518B1 (ko) | 2012-01-16 | 2012-11-14 | 포항공과대학교 산학협력단 | 갈로실리케이트 제올라이트 및 그 제조 방법 |
-
2013
- 2013-03-11 US US13/792,667 patent/US8609921B1/en not_active Expired - Fee Related
- 2013-11-12 US US14/077,331 patent/US8704026B1/en not_active Expired - Fee Related
- 2013-12-06 JP JP2015544219A patent/JP2016503430A/ja not_active Withdrawn
- 2013-12-06 ES ES13863150.2T patent/ES2663021T3/es active Active
- 2013-12-06 CN CN201380064568.3A patent/CN104870407B/zh not_active Expired - Fee Related
- 2013-12-06 EP EP13863150.2A patent/EP2931686B1/en not_active Not-in-force
- 2013-12-06 WO PCT/US2013/073462 patent/WO2014093143A1/en not_active Ceased
- 2013-12-06 KR KR1020157012181A patent/KR20150066584A/ko not_active Withdrawn
- 2013-12-06 RU RU2015128053A patent/RU2015128053A/ru unknown
- 2013-12-06 SG SG11201502366UA patent/SG11201502366UA/en unknown
- 2013-12-06 IN IN2491DEN2015 patent/IN2015DN02491A/en unknown
- 2013-12-12 TW TW102145961A patent/TWI508945B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016503430A (ja) | 2016-02-04 |
| EP2931686A4 (en) | 2016-08-17 |
| WO2014093143A1 (en) | 2014-06-19 |
| EP2931686B1 (en) | 2018-02-14 |
| TWI508945B (zh) | 2015-11-21 |
| US8704026B1 (en) | 2014-04-22 |
| US8609921B1 (en) | 2013-12-17 |
| KR20150066584A (ko) | 2015-06-16 |
| TW201427939A (zh) | 2014-07-16 |
| CN104870407B (zh) | 2017-04-05 |
| CN104870407A (zh) | 2015-08-26 |
| EP2931686A1 (en) | 2015-10-21 |
| RU2015128053A (ru) | 2017-01-16 |
| SG11201502366UA (en) | 2015-04-29 |
| IN2015DN02491A (enExample) | 2015-09-11 |
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