CS207609B2 - Způsob katalytické isomerace monocyklických mcthylsubstituovaných aromatických uhlovodíků - Google Patents

Způsob katalytické isomerace monocyklických mcthylsubstituovaných aromatických uhlovodíků Download PDF

Info

Publication number: CS207609B2
Authority: CS; Czechoslovakia
Prior art keywords: zsm; zeolite; xylene; hydrogen; alumina
Prior art date: 1977-05-09

Application number

CS297178A

Other languages

Czech (cs)

English (en)

Inventor

Roger A Morrison

Samuel A Tabak

Original Assignee

Mobil Oil Corp

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.)

1977-05-09

Filing date

1978-05-10

Publication date

1981-08-31

1978-05-10 Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp

1981-08-31 Publication of CS207609B2 publication Critical patent/CS207609B2/cs

Links

238000000034 method Methods 0.000 title claims description 39
238000006317 isomerization reaction Methods 0.000 title claims description 23
150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 6
239000010457 zeolite Substances 0.000 claims description 82
239000003054 catalyst Substances 0.000 claims description 69
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 69
229910021536 Zeolite Inorganic materials 0.000 claims description 58
239000000203 mixture Substances 0.000 claims description 53
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 42
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 41
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
230000008569 process Effects 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
229910052751 metal Inorganic materials 0.000 claims description 19
239000002184 metal Substances 0.000 claims description 19
150000001768 cations Chemical class 0.000 claims description 18
239000000377 silicon dioxide Substances 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
229910000323 aluminium silicate Inorganic materials 0.000 claims description 12
229930195733 hydrocarbon Natural products 0.000 claims description 12
150000002430 hydrocarbons Chemical class 0.000 claims description 12
229910052697 platinum Inorganic materials 0.000 claims description 12
229910052593 corundum Inorganic materials 0.000 claims description 11
229910001845 yogo sapphire Inorganic materials 0.000 claims description 11
230000000737 periodic effect Effects 0.000 claims description 10
239000004215 Carbon black (E152) Substances 0.000 claims description 8
239000011230 binding agent Substances 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
229910052759 nickel Inorganic materials 0.000 claims description 6
239000007789 gas Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
239000002243 precursor Substances 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
229910017052 cobalt Inorganic materials 0.000 claims description 3
239000010941 cobalt Substances 0.000 claims description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 42
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 37
239000008096 xylene Substances 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 24
-1 aluminum chloride Chemical class 0.000 description 17
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 15
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
239000011148 porous material Substances 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 8
229910052681 coesite Inorganic materials 0.000 description 8
229910052906 cristobalite Inorganic materials 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
229910052682 stishovite Inorganic materials 0.000 description 8
229910052905 tridymite Inorganic materials 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
229940078552 o-xylene Drugs 0.000 description 7
150000003738 xylenes Chemical class 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
238000007323 disproportionation reaction Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
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 5
239000000571 coke Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001477 organic nitrogen group Chemical group 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000002585 base Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012634 fragment Substances 0.000 description 3
239000001307 helium Substances 0.000 description 3
229910052734 helium Inorganic materials 0.000 description 3
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
150000002892 organic cations Chemical class 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
FYGHSUNMUKGBRK-UHFFFAOYSA-N trimethylbenzene Natural products CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 3
BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000004115 Sodium Silicate Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 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
239000007864 aqueous solution Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 2
238000001354 calcination Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229910001603 clinoptilolite Inorganic materials 0.000 description 2
238000005336 cracking Methods 0.000 description 2
230000020335 dealkylation Effects 0.000 description 2
238000006900 dealkylation reaction Methods 0.000 description 2
SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
229910001657 ferrierite group Inorganic materials 0.000 description 2
238000010304 firing Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
230000006872 improvement Effects 0.000 description 2
229910052809 inorganic oxide Inorganic materials 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
238000000634 powder X-ray diffraction Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000002407 reforming Methods 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000010703 silicon Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000011282 treatment Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
MEGFZVZIOCKTCS-UHFFFAOYSA-N 1,2,3,4-tetramethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1C.CC1=CC=C(C)C(C)=C1C MEGFZVZIOCKTCS-UHFFFAOYSA-N 0.000 description 1
WZEYZMKZKQPXSX-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1.CC1=CC(C)=CC(C)=C1 WZEYZMKZKQPXSX-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
238000001994 activation Methods 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
239000011449 brick Substances 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
150000005195 diethylbenzenes Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
229910052675 erionite Inorganic materials 0.000 description 1
235000012438 extruded product Nutrition 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000007863 gel particle Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
229910052677 heulandite Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052680 mordenite Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001388 sodium aluminate Inorganic materials 0.000 description 1
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
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
235000019351 sodium silicates Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000010555 transalkylation reaction Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000011800 void material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

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

CS297178A 1977-05-09 1978-05-10 Způsob katalytické isomerace monocyklických mcthylsubstituovaných aromatických uhlovodíků CS207609B2 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US79504677A	1977-05-09	1977-05-09

Publications (1)

Publication Number	Publication Date
CS207609B2 true CS207609B2 (cs)	1981-08-31

Family

ID=25164510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS297178A CS207609B2 (cs)	1977-05-09	1978-05-10	Způsob katalytické isomerace monocyklických mcthylsubstituovaných aromatických uhlovodíků

Country Status (3)

Country	Link
CS (1)	CS207609B2 (pl)
PL (1)	PL124493B1 (pl)
ZA (1)	ZA782069B (pl)

1978
- 1978-04-11 ZA ZA00782069A patent/ZA782069B/xx unknown
- 1978-05-05 PL PL20664878A patent/PL124493B1/pl unknown
- 1978-05-10 CS CS297178A patent/CS207609B2/cs unknown

Also Published As

Publication number	Publication date
ZA782069B (en)	1979-11-28
PL124493B1 (en)	1983-01-31
PL206648A1 (pl)	1979-08-13

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US4694114A (en)	1987-09-15	Process for isomerizing alkyl aromatic hydrocarbons utilizing ZSM-23 zeolite and a hydrogenation/dehydrogenation metal
CS199682B2 (en)	1980-07-31	Process for the ethylation of toluene or ethylbenzene
JPH0567613B1 (pl)	1993-09-27
NO303677B1 (no)	1998-08-17	Zeolitt-katalysator, fremgangsmÕte for fremstilling derav og fremgangsmÕte for anvendelse derav
EA002220B1 (ru)	2002-02-28	Цеолитный катализатор и его использование для конверсии углеводородов
WO1997045384A9 (en)	1998-07-02	Aromatic conversion processes and zeolite catalyst useful therein
JP2008501001A (ja)	2008-01-17	有機化合物のアルキル交換／脱アルキル用触媒と触媒法
US4104319A (en)	1978-08-01	Ethylation of mono alkyl benzene
US4152363A (en)	1979-05-01	Vapor phase isomerization of methyl-substituted aromatic hydrocarbons improved by using highly diluted zeolite catalyst
EP0087720B2 (fr)	1993-03-31	Zéolite cristalline en silicate d'aluminium
MXPA01011229A (es)	2002-10-04	Catalizador de zeolita ligada con zeolita, a la medida, y su uso conversion de hidrocarburos.
EA001597B1 (ru)	2001-06-25	Способ изомеризации алкилароматических углеводородов
CS207496B1 (en)	1981-07-31	method of isomerization of the xylene
US5254770A (en)	1993-10-19	Isomerization of aromatic compounds over ZSM-22 zeolite
JPH0140656B2 (pl)	1989-08-30
EP0021600B1 (en)	1983-02-02	Selective alkylation of xylenes with ethylene