GB1574523A - Process for producing p-diakyl substituted benzenes and catalyst therefor - Google Patents
Process for producing p-diakyl substituted benzenes and catalyst therefor Download PDFInfo
- Publication number
- GB1574523A GB1574523A GB12642/77A GB1264277A GB1574523A GB 1574523 A GB1574523 A GB 1574523A GB 12642/77 A GB12642/77 A GB 12642/77A GB 1264277 A GB1264277 A GB 1264277A GB 1574523 A GB1574523 A GB 1574523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- catalyst
- zeolite
- percent
- xylene
- catalyst according
- 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.)
- Expired
Links
- 239000003054 catalyst Chemical class 0.000 title claims description 258
- 238000000034 method Methods 0.000 title claims description 47
- 230000008569 process Effects 0.000 title claims description 29
- 150000001555 benzenes Chemical class 0.000 title claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 402
- 239000010457 zeolite Substances 0.000 claims description 194
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 190
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 182
- 229910021536 Zeolite Inorganic materials 0.000 claims description 163
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 138
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 130
- 239000008096 xylene Substances 0.000 claims description 125
- 238000006243 chemical reaction Methods 0.000 claims description 105
- 238000001179 sorption measurement Methods 0.000 claims description 74
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 62
- 239000000377 silicon dioxide Substances 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000013078 crystal Substances 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 48
- 150000002430 hydrocarbons Chemical class 0.000 claims description 46
- 229930195733 hydrocarbon Natural products 0.000 claims description 45
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 239000000571 coke Substances 0.000 claims description 35
- 239000012298 atmosphere Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 amino, methoxy Chemical group 0.000 claims description 30
- 229910052698 phosphorus Inorganic materials 0.000 claims description 24
- 239000011574 phosphorus Substances 0.000 claims description 24
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 239000011230 binding agent Substances 0.000 claims description 18
- 229920001296 polysiloxane Polymers 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 17
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 17
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 16
- 239000011777 magnesium Substances 0.000 claims description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052749 magnesium Inorganic materials 0.000 claims description 15
- 239000011148 porous material Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000395 magnesium oxide Substances 0.000 claims description 13
- 150000003377 silicon compounds Chemical class 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 9
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 claims description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims description 6
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- CCDWGDHTPAJHOA-UHFFFAOYSA-N benzylsilicon Chemical compound [Si]CC1=CC=CC=C1 CCDWGDHTPAJHOA-UHFFFAOYSA-N 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 claims description 5
- LTPBRCUWZOMYOC-UHFFFAOYSA-N Beryllium oxide Chemical compound O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 239000012188 paraffin wax Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 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 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- HIHIPCDUFKZOSL-UHFFFAOYSA-N ethenyl(methyl)silicon Chemical compound C[Si]C=C HIHIPCDUFKZOSL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 2
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 claims description 2
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 2
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 claims description 2
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 67
- 150000003738 xylenes Chemical class 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 229910001868 water Inorganic materials 0.000 description 52
- 239000000047 product Substances 0.000 description 48
- 239000003570 air Substances 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 30
- 229910052753 mercury Inorganic materials 0.000 description 30
- 229910052681 coesite Inorganic materials 0.000 description 20
- 229910052906 cristobalite Inorganic materials 0.000 description 20
- 235000012239 silicon dioxide Nutrition 0.000 description 20
- 229910052682 stishovite Inorganic materials 0.000 description 20
- 229910052905 tridymite Inorganic materials 0.000 description 20
- 238000001354 calcination Methods 0.000 description 19
- 238000013019 agitation Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 17
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 238000007323 disproportionation reaction Methods 0.000 description 13
- 239000000499 gel Substances 0.000 description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 12
- 239000012263 liquid product Substances 0.000 description 12
- 238000002441 X-ray diffraction Methods 0.000 description 11
- 229910052593 corundum Inorganic materials 0.000 description 11
- 229910001657 ferrierite group Inorganic materials 0.000 description 11
- 239000012265 solid product Substances 0.000 description 11
- 229910001845 yogo sapphire Inorganic materials 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 10
- 150000001768 cations Chemical class 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 230000036961 partial effect Effects 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 9
- 239000008188 pellet Substances 0.000 description 9
- 239000004115 Sodium Silicate Substances 0.000 description 8
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 8
- 235000011128 aluminium sulphate Nutrition 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000005342 ion exchange Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 229940078552 o-xylene Drugs 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 8
- 229910052911 sodium silicate Inorganic materials 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 7
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 7
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 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 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000008929 regeneration Effects 0.000 description 7
- 238000011069 regeneration method Methods 0.000 description 7
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000001477 organic nitrogen group Chemical group 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229940097364 magnesium acetate tetrahydrate Drugs 0.000 description 5
- XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000002210 silicon-based material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 5
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 238000004939 coking Methods 0.000 description 4
- QHMGJGNTMQDRQA-UHFFFAOYSA-N dotriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC QHMGJGNTMQDRQA-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000012022 methylating agents Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- KUPLEGDPSCCPJI-UHFFFAOYSA-N tetracontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC KUPLEGDPSCCPJI-UHFFFAOYSA-N 0.000 description 4
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
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- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N pentadiene group Chemical class C=CC=CC PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical class PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical group S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- HKMHSMCTSWRGAV-UHFFFAOYSA-N toluene;1,4-xylene Chemical compound CC1=CC=CC=C1.CC1=CC=C(C)C=C1 HKMHSMCTSWRGAV-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- KEUYHGXCOWNTEJ-UHFFFAOYSA-N trimethyl stiborite Chemical compound [Sb+3].[O-]C.[O-]C.[O-]C KEUYHGXCOWNTEJ-UHFFFAOYSA-N 0.000 description 1
- VEDJZFSRVVQBIL-UHFFFAOYSA-N trisilane Chemical class [SiH3][SiH2][SiH3] VEDJZFSRVVQBIL-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical class [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
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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
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- 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
- C07C6/123—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 only one hydrocarbon
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- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
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- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
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- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
- C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
- C07C5/41—Catalytic processes
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- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/12—After treatment, characterised by the effect to be obtained to alter the outside of the crystallites, e.g. selectivation
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- B01J2229/30—After treatment, characterised by the means used
- B01J2229/32—Reaction with silicon compounds, e.g. TEOS, siliconfluoride
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-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2229/30—After treatment, characterised by the means used
- B01J2229/42—Addition of matrix or binder particles
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively
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- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
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- 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
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
-
- 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
- C07C2529/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/672,194 US4060568A (en) | 1976-03-31 | 1976-03-31 | Silica-modified zeolite catalyst and conversion therewith |
US05/680,998 US4011276A (en) | 1976-04-28 | 1976-04-28 | Disproportionation of toluene |
US68587276A | 1976-05-12 | 1976-05-12 | |
US68586976A | 1976-05-12 | 1976-05-12 | |
US05/726,091 US4090981A (en) | 1976-09-23 | 1976-09-23 | Catalyst for selective production of para dialkyl substituted benzenes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1574523A true GB1574523A (en) | 1980-09-10 |
Family
ID=27542059
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12642/77A Expired GB1574523A (en) | 1976-03-31 | 1977-03-25 | Process for producing p-diakyl substituted benzenes and catalyst therefor |
Country Status (12)
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4357264A (en) | 1980-03-10 | 1982-11-02 | Mobil Oil Corporation | Alkaline earth metal modified zeolite catalysts |
US4899009A (en) * | 1987-09-09 | 1990-02-06 | Nippon Petrochemicals Co. Ltd. | Method for producing m-benzyltolune |
US4902841A (en) * | 1987-03-11 | 1990-02-20 | Nippon Petrochemicals Company, Ltd. | Method for producing electrical insulating oil composition |
US4982025A (en) * | 1988-03-09 | 1991-01-01 | Nippon Petrochemicals Company, Limited | Electrical insulating oil comprising improved fraction |
WO2004108282A3 (en) * | 2003-06-03 | 2005-03-31 | Chevron Phillips Chemical Co | Selective para-xylene production via methylation of toluene with methanol in the presence of modified hzsm-5 catalyst |
US7799962B2 (en) | 2003-12-31 | 2010-09-21 | Exxonmobil Chemical Patents Inc. | Process for aromatic alkylation |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ183608A (en) * | 1976-03-31 | 1978-12-18 | Mobil Oil Corp | Aluminosilicate zeolite catalyst for selectine production of para-diakyl substituted benzenes |
US4086287A (en) * | 1976-07-19 | 1978-04-25 | Mobil Oil Corporation | Selective ethylation of mono alkyl benzenes |
US4104319A (en) * | 1977-06-23 | 1978-08-01 | Mobil Oil Corporation | Ethylation of mono alkyl benzene |
US4117024A (en) * | 1977-07-29 | 1978-09-26 | Mobil Oil Corporation | Ethylation of aromatic compounds |
FR2417540A1 (fr) * | 1978-02-20 | 1979-09-14 | Shell France | Procede de craquage catalytique d'hydrocarbures et catalyseur pour la mise en oeuvre du procede |
FR2442881A2 (fr) * | 1978-11-29 | 1980-06-27 | Shell France | Procede de craquage catalytique d'hydrocarbures, et catalyseur pour la mise en oeuvre du procede |
AU538578B2 (en) * | 1979-01-31 | 1984-08-23 | Mobil Oil Corp. | Zeolite catalyst containing gp za or gp8 metal and its use to convert hydrocarbons |
US4274982A (en) * | 1979-10-12 | 1981-06-23 | Mobil Oil Corporation | Method for maintaining para-selectivity of modified zeolite catalyst |
US4288647A (en) * | 1980-03-10 | 1981-09-08 | Mobil Oil Corporation | Shape selective reactions with alkaline earth-modified zeolite catalysts |
US4278827A (en) * | 1980-04-07 | 1981-07-14 | Mobil Oil Corporation | Shape selective reactions with zeolite catalyst modified with group IVB metal |
EP0040463B1 (en) * | 1980-05-19 | 1984-09-05 | Mobil Oil Corporation | Shape selective reactions with zeolite catalyst modified with iron and/or cobalt |
JPS57108023A (en) * | 1980-12-26 | 1982-07-05 | Toa Nenryo Kogyo Kk | Oligomerization catalyst for isobutene |
US4431527A (en) * | 1981-11-13 | 1984-02-14 | Standard Oil Company (Indiana) | Process for hydrogen treating high nitrogen content hydrocarbon feeds |
JPS5931718A (ja) * | 1982-08-17 | 1984-02-20 | Toray Ind Inc | パラジアルキルベンゼンの選択的製造法 |
JPS59107921A (ja) * | 1982-12-10 | 1984-06-22 | Idemitsu Kosan Co Ltd | p―キシレンの製造方法 |
ZA845190B (en) * | 1983-08-19 | 1986-02-26 | Mobil Oil Corp | A process for preparing a coked zeolite catalyst and a process for the selective disproportionation of toluene using said catalyst |
EP0134076B1 (en) * | 1983-08-19 | 1988-10-26 | Mobil Oil Corporation | A process for preparing a coked zeolite catalyst and a process for the selective disproportionation of toluene using said catalyst |
US4613717A (en) * | 1984-06-25 | 1986-09-23 | Research Association For Utilization Of Light Oil | Process for producing a 1,4-dialkylbenzene |
JPS61221137A (ja) * | 1985-03-28 | 1986-10-01 | Teijin Yuka Kk | P−キシレンの製造法 |
JPS6263528A (ja) * | 1985-09-17 | 1987-03-20 | Teijin Yuka Kk | P−キシレンの製造法 |
JPS62115088A (ja) * | 1985-11-13 | 1987-05-26 | Res Assoc Util Of Light Oil | 芳香族炭化水素の製造方法 |
US4849386A (en) * | 1987-04-08 | 1989-07-18 | Taiwan Styrene Monomer Corporation | Novel silicon-modified catalyst Si/HZSM-5 preparation |
US4851604A (en) * | 1987-09-02 | 1989-07-25 | Mobil Oil Corp. | Toluene disproportionation |
KR940002885B1 (ko) * | 1989-03-22 | 1994-04-06 | 마쯔시다레이끼 가부시기가이샤 | 발포단열재 |
BR9007077A (pt) * | 1989-12-13 | 1992-03-03 | Mobil Oil Corp | Processo para conversao de estoque de provisao |
US5448005A (en) * | 1994-04-04 | 1995-09-05 | Mobil Oil Corporation | Crystallization of paraxlene from high purity paraxylene feeds |
JP3427507B2 (ja) * | 1994-09-12 | 2003-07-22 | 東レ株式会社 | パラジアルキルベンゼンの製造用触媒及びその製造法及びパラキシレンを製造する方法 |
DE19538799A1 (de) * | 1995-10-18 | 1997-04-24 | Sued Chemie Ag | Wabenförmiger Katalysatorträger |
US6316683B1 (en) * | 1999-06-07 | 2001-11-13 | Exxonmobil Chemical Patents Inc. | Protecting catalytic activity of a SAPO molecular sieve |
US6709570B1 (en) * | 1999-09-27 | 2004-03-23 | Shell Oil Company | Method for preparing a catalyst |
JP5294928B2 (ja) * | 2009-03-06 | 2013-09-18 | 三井化学株式会社 | 芳香族炭化水素の製造方法およびその製造方法に使用される触媒 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
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US2722504A (en) * | 1950-12-04 | 1955-11-01 | Union Oil Co | Silicone coated catalyst and use thereof |
US3417157A (en) * | 1967-12-28 | 1968-12-17 | Universal Oil Prod Co | Transalkylation of toluene and catalyst therefor |
US3525775A (en) * | 1968-03-29 | 1970-08-25 | Union Carbide Corp | Catalytic xylene isomerization process and catalyst therefor |
US3651162A (en) * | 1969-02-27 | 1972-03-21 | Standard Oil Co | Isomerization and disproportionation of alkyl aromatics |
US3658696A (en) * | 1969-06-17 | 1972-04-25 | Texaco Inc | Selected adsorption with a silanized crystalline alumino-silicate |
US3790471A (en) * | 1969-10-10 | 1974-02-05 | Mobil Oil Corp | Conversion with zsm-5 family of crystalline aluminosilicate zeolites |
US3702886A (en) * | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
US3682996A (en) * | 1970-02-24 | 1972-08-08 | Mobil Oil Corp | Zeolite esters |
US3832449A (en) * | 1971-03-18 | 1974-08-27 | Mobil Oil Corp | Crystalline zeolite zsm{14 12 |
US3698157A (en) * | 1971-06-01 | 1972-10-17 | Mobil Oil Corp | Separation of mixtures with modified zeolites |
GB1403329A (en) * | 1972-04-28 | 1975-08-28 | Mobil Oil Corp | Vapour-phase alkylation in presence of crystalline alumino silicate catalyst |
US3751504A (en) * | 1972-05-12 | 1973-08-07 | Mobil Oil Corp | Vapor-phase alkylation in presence of crystalline aluminosilicate catalyst with separate transalkylation |
US3808284A (en) * | 1972-09-11 | 1974-04-30 | Texaco Inc | Process for disproportionating hydrocarbons |
US3894104A (en) * | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Aromatization of hetero-atom substituted hydrocarbons |
US3890218A (en) * | 1974-03-29 | 1975-06-17 | Mobil Oil Corp | Upgrading aliphatic naphthas to higher octane gasoline |
CA1062285A (en) * | 1974-04-24 | 1979-09-11 | Mobil Oil Corporation | Conversion of synthesis gas to hydrocarbon mixtures |
US3980586A (en) * | 1974-08-28 | 1976-09-14 | Mobil Oil Corporation | Modified solid catalyst materials |
NZ178543A (en) * | 1974-09-23 | 1978-04-03 | Mobil Oil Corp | Conversion catalyst, crystalline alumin osilicate zeolite containing phosphorus |
US4016218A (en) * | 1975-05-29 | 1977-04-05 | Mobil Oil Corporation | Alkylation in presence of thermally modified crystalline aluminosilicate catalyst |
NZ183608A (en) * | 1976-03-31 | 1978-12-18 | Mobil Oil Corp | Aluminosilicate zeolite catalyst for selectine production of para-diakyl substituted benzenes |
US4086262A (en) * | 1976-09-20 | 1978-04-25 | Mobil Oil Corporation | Conversion of synthesis gas to hydrocarbon mixtures |
-
1977
- 1977-03-15 NZ NZ183608A patent/NZ183608A/xx unknown
- 1977-03-24 BE BE176109A patent/BE852865A/xx not_active IP Right Cessation
- 1977-03-25 FR FR7708958A patent/FR2357303A1/fr active Granted
- 1977-03-25 GB GB12642/77A patent/GB1574523A/en not_active Expired
- 1977-03-28 NO NO771085A patent/NO149492C/no unknown
- 1977-03-29 IT IT21852/77A patent/IT1075368B/it active
- 1977-03-29 SE SE7703593A patent/SE438606B/xx not_active IP Right Cessation
- 1977-03-30 CS CS772120A patent/CS218565B2/cs unknown
- 1977-03-30 DE DE2760481A patent/DE2760481C2/de not_active Expired - Lifetime
- 1977-03-30 NL NLAANVRAGE7703484,A patent/NL187424C/xx not_active IP Right Cessation
- 1977-03-30 DE DE19772714239 patent/DE2714239A1/de active Granted
- 1977-03-30 DE DE2760479A patent/DE2760479C2/de not_active Expired - Lifetime
- 1977-03-31 PL PL1977197088A patent/PL115528B1/pl unknown
- 1977-03-31 JP JP3555877A patent/JPS52120292A/ja active Granted
-
1988
- 1988-10-21 JP JP63264259A patent/JPH01199920A/ja active Pending
- 1988-10-21 JP JP63264259A patent/JPH0567613B1/ja active Pending
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4357264A (en) | 1980-03-10 | 1982-11-02 | Mobil Oil Corporation | Alkaline earth metal modified zeolite catalysts |
US4902841A (en) * | 1987-03-11 | 1990-02-20 | Nippon Petrochemicals Company, Ltd. | Method for producing electrical insulating oil composition |
US4899009A (en) * | 1987-09-09 | 1990-02-06 | Nippon Petrochemicals Co. Ltd. | Method for producing m-benzyltolune |
US4982025A (en) * | 1988-03-09 | 1991-01-01 | Nippon Petrochemicals Company, Limited | Electrical insulating oil comprising improved fraction |
WO2004108282A3 (en) * | 2003-06-03 | 2005-03-31 | Chevron Phillips Chemical Co | Selective para-xylene production via methylation of toluene with methanol in the presence of modified hzsm-5 catalyst |
US7049260B2 (en) | 2003-06-03 | 2006-05-23 | Chevron Phillips Chemical Company Lp | Selective para-xylene production via methylation of toluene with methanol in the presence of modified HZSM-5 catalyst |
US7323430B2 (en) | 2003-06-03 | 2008-01-29 | Chevron Phillips Chemical Company Lp | Selective para-xylene production via methylation of toluene with methanol in the presence of modified HZSM-5 catalyst |
US7387978B2 (en) | 2003-06-03 | 2008-06-17 | Chevron Phillips Chemical Company Lp | Selective para-xylene production via methylation of toluene with methanol in the presence of modified HZSM-5 catalyst |
US7799962B2 (en) | 2003-12-31 | 2010-09-21 | Exxonmobil Chemical Patents Inc. | Process for aromatic alkylation |
Also Published As
Publication number | Publication date |
---|---|
NL187424C (nl) | 1991-10-01 |
JPS52120292A (en) | 1977-10-08 |
DE2760479C2 (enrdf_load_stackoverflow) | 1993-08-12 |
FR2357303A1 (fr) | 1978-02-03 |
SE7703593L (sv) | 1977-10-01 |
SE438606B (sv) | 1985-04-29 |
NL7703484A (nl) | 1977-10-04 |
DE2714239A1 (de) | 1977-10-20 |
DE2714239C2 (enrdf_load_stackoverflow) | 1993-07-22 |
CS218565B2 (en) | 1983-02-25 |
NO149492C (no) | 1984-05-09 |
JPH01199920A (ja) | 1989-08-11 |
BE852865A (fr) | 1977-09-26 |
NZ183608A (en) | 1978-12-18 |
FR2357303B1 (enrdf_load_stackoverflow) | 1984-06-01 |
PL115528B1 (en) | 1981-04-30 |
DE2760481C2 (enrdf_load_stackoverflow) | 1993-07-15 |
NL187424B (nl) | 1991-05-01 |
JPH0567613B1 (enrdf_load_stackoverflow) | 1993-09-27 |
JPS6247854B2 (enrdf_load_stackoverflow) | 1987-10-09 |
NO149492B (no) | 1984-01-23 |
NO771085L (no) | 1977-10-03 |
IT1075368B (it) | 1985-04-22 |
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PS | Patent sealed [section 19, patents act 1949] | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19970324 |