CA1090315A - Procede d'obtention de benzenes p-dialkyles catalyseur de la reaction - Google Patents

Procede d'obtention de benzenes p-dialkyles catalyseur de la reaction

Info

Publication number: CA1090315A
Authority: CA; Canada
Prior art keywords: catalyst; zeolite; xylene; percent; toluene
Prior art date: 1976-05-12
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

Application number

CA275,126A

Other languages

English (en)

Inventor

Werner O. Haag

David H. Olson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

Priority date (The priority date 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 date listed.)

1976-05-12

Filing date

1977-03-30

Publication date

1980-11-25

1977-03-30 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1980-11-25 Application granted granted Critical

1980-11-25 Publication of CA1090315A publication Critical patent/CA1090315A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Chemical class 0.000 title claims abstract description 244
150000001555 benzenes Chemical class 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims description 45
230000008569 process Effects 0.000 title claims description 28
239000010457 zeolite Substances 0.000 claims abstract description 204
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 190
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 172
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 143
239000008096 xylene Substances 0.000 claims abstract description 101
238000001179 sorption measurement Methods 0.000 claims abstract description 75
230000000694 effects Effects 0.000 claims abstract description 19
229910000323 aluminium silicate Inorganic materials 0.000 claims abstract description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 394
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 204
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 113
238000006243 chemical reaction Methods 0.000 claims description 100
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 71
239000013078 crystal Substances 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 53
229910052739 hydrogen Inorganic materials 0.000 claims description 53
239000000377 silicon dioxide Substances 0.000 claims description 53
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
239000000571 coke Substances 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
239000012298 atmosphere Substances 0.000 claims description 33
-1 hydrogen cations Chemical class 0.000 claims description 33
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 28
229910052698 phosphorus Inorganic materials 0.000 claims description 28
239000011574 phosphorus Substances 0.000 claims description 28
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 26
239000011230 binding agent Substances 0.000 claims description 21
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 19
239000011777 magnesium Substances 0.000 claims description 19
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 claims description 18
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 18
229910052749 magnesium Inorganic materials 0.000 claims description 18
DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
229910052681 coesite Inorganic materials 0.000 claims description 14
229910052906 cristobalite Inorganic materials 0.000 claims description 14
239000000395 magnesium oxide Substances 0.000 claims description 14
235000012239 silicon dioxide Nutrition 0.000 claims description 14
229910052682 stishovite Inorganic materials 0.000 claims description 14
229910052905 tridymite Inorganic materials 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
235000012245 magnesium oxide Nutrition 0.000 claims description 13
150000001336 alkenes Chemical class 0.000 claims description 11
229910052796 boron Inorganic materials 0.000 claims description 7
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
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
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 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
229910052787 antimony Inorganic materials 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
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 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
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
229910052901 montmorillonite Inorganic materials 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 claims description 2
229910052593 corundum Inorganic materials 0.000 claims 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims 1
229910001845 yogo sapphire Inorganic materials 0.000 claims 1
239000000243 solution Substances 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
229910001868 water Inorganic materials 0.000 description 52
239000000047 product Substances 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
150000001875 compounds Chemical class 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
239000003570 air Substances 0.000 description 39
150000003738 xylenes Chemical class 0.000 description 38
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 30
229910052753 mercury Inorganic materials 0.000 description 30
235000014786 phosphorus Nutrition 0.000 description 27
229920001296 polysiloxane Polymers 0.000 description 21
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 20
238000001354 calcination Methods 0.000 description 19
239000007788 liquid Substances 0.000 description 19
238000010438 heat treatment Methods 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
238000013019 agitation Methods 0.000 description 17
235000001055 magnesium Nutrition 0.000 description 17
229940091250 magnesium supplement Drugs 0.000 description 17
150000002431 hydrogen Chemical class 0.000 description 16
238000004519 manufacturing process Methods 0.000 description 15
239000000499 gel Substances 0.000 description 14
238000007323 disproportionation reaction Methods 0.000 description 13
239000011148 porous material Substances 0.000 description 13
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000012263 liquid product Substances 0.000 description 12
238000002441 X-ray diffraction Methods 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 11
150000001768 cations Chemical class 0.000 description 11
229910001657 ferrierite group Inorganic materials 0.000 description 11
230000036961 partial effect Effects 0.000 description 11
239000012265 solid product Substances 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
238000005259 measurement Methods 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 9
150000001340 alkali metals Chemical class 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
238000001035 drying Methods 0.000 description 9
229960000869 magnesium oxide Drugs 0.000 description 9
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
229940078552 o-xylene Drugs 0.000 description 9
229910001392 phosphorus oxide Inorganic materials 0.000 description 9
150000003377 silicon compounds Chemical class 0.000 description 9
VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 9
239000004115 Sodium Silicate Substances 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
238000005342 ion exchange Methods 0.000 description 8
238000002156 mixing Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
125000001477 organic nitrogen group Chemical group 0.000 description 8
239000008188 pellet Substances 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
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
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
239000005977 Ethylene Substances 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
229910000272 alkali metal oxide Inorganic materials 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 7
108091006629 SLC13A2 Proteins 0.000 description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
239000011248 coating agent Substances 0.000 description 6
238000000576 coating method Methods 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
239000002243 precursor Substances 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
230000008929 regeneration Effects 0.000 description 6
238000011069 regeneration method Methods 0.000 description 6
229910052710 silicon Inorganic materials 0.000 description 6
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
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 5
230000015572 biosynthetic process Effects 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 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
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910000077 silane Inorganic materials 0.000 description 5
239000010703 silicon Substances 0.000 description 5
239000002210 silicon-based material Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 5
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000032683 aging Effects 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
CCDWGDHTPAJHOA-UHFFFAOYSA-N benzylsilicon Chemical compound [Si]CC1=CC=CC=C1 CCDWGDHTPAJHOA-UHFFFAOYSA-N 0.000 description 4
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000001307 helium Substances 0.000 description 4
229910052734 helium Inorganic materials 0.000 description 4
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
150000002681 magnesium compounds Chemical class 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
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 4
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
KUPLEGDPSCCPJI-UHFFFAOYSA-N tetracontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC KUPLEGDPSCCPJI-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
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
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000001273 butane Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010908 decantation Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
230000008021 deposition Effects 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000011987 methylation Effects 0.000 description 3
238000007069 methylation reaction Methods 0.000 description 3
150000002892 organic cations Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
150000004756 silanes Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000003463 sulfur Chemical class 0.000 description 3
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000002411 adverse Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910001413 alkali metal ion Inorganic materials 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
JYIBXUUINYLWLR-UHFFFAOYSA-N aluminum;calcium;potassium;silicon;sodium;trihydrate Chemical compound O.O.O.[Na].[Al].[Si].[K].[Ca] JYIBXUUINYLWLR-UHFFFAOYSA-N 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
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230000002311 subsequent effect Effects 0.000 description 1
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
229920002994 synthetic fiber Polymers 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation 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
239000012808 vapor phase Substances 0.000 description 1
239000011800 void material Substances 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA275,126A 1976-05-12 1977-03-30 Procede d'obtention de benzenes p-dialkyles catalyseur de la reaction Expired CA1090315A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US68586976A	1976-05-12	1976-05-12
US68587276A	1976-05-12	1976-05-12
US685,869		1976-05-12
US685,872		1976-05-12

Publications (1)

Publication Number	Publication Date
CA1090315A true CA1090315A (fr)	1980-11-25

Family

ID=27103692

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA275,126A Expired CA1090315A (fr)	1976-05-12	1977-03-30	Procede d'obtention de benzenes p-dialkyles catalyseur de la reaction

Country Status (1)

Country	Link
CA (1)	CA1090315A (fr)

1977
- 1977-03-30 CA CA275,126A patent/CA1090315A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-11-25	MKEX	Expiry

Publication	Publication Date	Title
CA1084532A (fr)	1980-08-26	Production selective de p-dialkylbenzenes
US4465886A (en)	1984-08-14	Silica-modified catalyst and use for selective production of para-dialkyl substituted benzenes
US4477583A (en)	1984-10-16	Silica-modified catalyst and use for selective production of para-dialkyl substituted benzenes
GB1574523A (en)	1980-09-10	Process for producing p-diakyl substituted benzenes and catalyst therefor
US4375573A (en)	1983-03-01	Selective production and reaction of p-Disubstituted aromatics over zeolite ZSM-48
CA1086707A (fr)	1980-09-30	Catalyseur et production selective de para- dialkylbenzenes a groupements substitues
US4117026A (en)	1978-09-26	Selective production of para dialkyl substituted benzenes
CA1113509A (fr)	1981-12-01	Isomerisation du xylene
US4113788A (en)	1978-09-12	Selective production of para-xylene
US4128592A (en)	1978-12-05	Selective production of para dialkyl benzene
CA1077455A (fr)	1980-05-13	Catalyseur a teneur d'antimoine, methode de preparation et emploi
US4117024A (en)	1978-09-26	Ethylation of aromatic compounds
US3965207A (en)	1976-06-22	Selective production of para-xylene
US3965208A (en)	1976-06-22	Methylation of toluene
US5569805A (en)	1996-10-29	Catalytic conversion of aromatic compounds
US4002697A (en)	1977-01-11	Selective production of para-xylene
US4100217A (en)	1978-07-11	Selective production of para-substituted benzenes
US4011276A (en)	1977-03-08	Disproportionation of toluene
CA1180307A (fr)	1985-01-02	Reactions selectives pour la configuration, utilisant des catalyseurs aux zeolites, modifies par des metaux du groupe ivb
US4143084A (en)	1979-03-06	Di-alkylbenzene isomer mixtures
US4250345A (en)	1981-02-10	Selective production of para-xylene
EP0137757A1 (fr)	1985-04-17	Alcoylation d'hydrocarbures aromatiques
US4524055A (en)	1985-06-18	Crystalline aluminosilicate zeolite and process for production thereof
US4695666A (en)	1987-09-22	Phosphorus-containing alumina catalyst for the isomerization of aromatics
US4152363A (en)	1979-05-01	Vapor phase isomerization of methyl-substituted aromatic hydrocarbons improved by using highly diluted zeolite catalyst