CS223832B2 - Method of isomeraion of xylene - Google Patents

Method of isomeraion of xylene Download PDF

Info

Publication number: CS223832B2
Authority: CS; Czechoslovakia
Prior art keywords: xylene; zeolite; catalyst; ethylbenzene; carbon atoms
Prior art date: 1979-05-21

Application number

CS803550A

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.)

1979-05-21

Filing date

1980-05-21

Publication date

1983-11-25

1980-05-21 Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp

1983-11-25 Publication of CS223832B2 publication Critical patent/CS223832B2/cs

Links

239000008096 xylene Substances 0.000 title claims abstract description 49
238000000034 method Methods 0.000 title claims description 57
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 title claims description 53
239000003054 catalyst Substances 0.000 claims abstract description 68
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 51
239000010457 zeolite Substances 0.000 claims abstract description 51
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 43
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 42
238000006317 isomerization reaction Methods 0.000 claims abstract description 33
150000003738 xylenes Chemical class 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims description 44
238000006243 chemical reaction Methods 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 23
150000001875 compounds Chemical class 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000011159 matrix material Substances 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 4
-1 alkali metal cation Chemical class 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 2
241000282941 Rangifer tarandus Species 0.000 claims 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract description 111
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 57
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 54
230000000694 effects Effects 0.000 abstract description 32
125000000217 alkyl group Chemical group 0.000 abstract description 6
239000006227 byproduct Substances 0.000 abstract description 4
230000009467 reduction Effects 0.000 abstract description 4
239000011959 amorphous silica alumina Substances 0.000 abstract description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 64
239000000047 product Substances 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 27
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 20
239000000377 silicon dioxide Substances 0.000 description 16
125000003118 aryl group Chemical group 0.000 description 15
239000000126 substance Substances 0.000 description 14
238000009835 boiling Methods 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 12
229940078552 o-xylene Drugs 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
150000001491 aromatic compounds Chemical class 0.000 description 8
238000007323 disproportionation reaction Methods 0.000 description 8
238000000926 separation method Methods 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
238000012360 testing method Methods 0.000 description 7
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000000638 solvent extraction Methods 0.000 description 6
230000008901 benefit Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000012188 paraffin wax Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
238000010025 steaming Methods 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
238000011282 treatment Methods 0.000 description 4
230000032683 aging Effects 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000005194 fractionation Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
230000007774 longterm Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
238000001354 calcination Methods 0.000 description 2
238000004517 catalytic hydrocracking Methods 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000000571 coke Substances 0.000 description 2
230000020335 dealkylation Effects 0.000 description 2
238000006900 dealkylation reaction Methods 0.000 description 2
238000013461 design Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000550 effect on aging Effects 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
239000000446 fuel Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
FDJSESZWPWMLEC-UHFFFAOYSA-N nonane Chemical compound CCCCCCCC[CH2+] FDJSESZWPWMLEC-UHFFFAOYSA-N 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
150000002892 organic cations Chemical class 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000010555 transalkylation reaction Methods 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052726 zirconium Inorganic materials 0.000 description 2
QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical class CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 1
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
NTOIMCSZPGZTND-UHFFFAOYSA-N 3,4-dihydro-1,2-benzoxathiine Chemical compound C1=CC=C2OSCCC2=C1 NTOIMCSZPGZTND-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000557626 Corvus corax Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000015511 Liquidambar orientalis Nutrition 0.000 description 1
241001311547 Patina Species 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000736858 Styrax americanus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
238000001994 activation Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
229940037003 alum Drugs 0.000 description 1
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 1
238000004458 analytical method Methods 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000012824 chemical production Methods 0.000 description 1
239000013064 chemical raw material Substances 0.000 description 1
229910001603 clinoptilolite Inorganic materials 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012084 conversion product Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
229910001649 dickite Inorganic materials 0.000 description 1
230000029087 digestion Effects 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
229940064259 eryc Drugs 0.000 description 1
238000013100 final test Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
229910052677 heulandite Inorganic materials 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000011738 major mineral Substances 0.000 description 1
235000011963 major mineral Nutrition 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000005172 methylbenzenes Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000035882 stress Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000035922 thirst Effects 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/08—Xylenes
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/18—Catalytic processes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
- C07C5/2737—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/26—After treatment, characterised by the effect to be obtained to stabilize the total catalyst structure
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/36—Steaming
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/42—Addition of matrix or binder particles
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Crystallography & Structural Chemistry (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CS803550A 1979-05-21 1980-05-21 Method of isomeraion of xylene CS223832B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/041,268 US4224141A (en)	1979-05-21	1979-05-21	Manufacture of aromatic compounds

Publications (1)

Publication Number	Publication Date
CS223832B2 true CS223832B2 (en)	1983-11-25

Family

ID=21915655

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS803550A CS223832B2 (en)	1979-05-21	1980-05-21	Method of isomeraion of xylene

Country Status (16)

Country	Link
US (1)	US4224141A (de)
EP (1)	EP0020043B1 (de)
JP (1)	JPS603368B2 (de)
AR (1)	AR220627A1 (de)
AT (1)	ATE1417T1 (de)
AU (1)	AU536713B2 (de)
CA (1)	CA1147353A (de)
CS (1)	CS223832B2 (de)
DE (1)	DE3060723D1 (de)
ES (1)	ES491630A0 (de)
HU (1)	HU184932B (de)
MX (1)	MX154768A (de)
NO (1)	NO153004C (de)
NZ (1)	NZ193796A (de)
PL (1)	PL224387A1 (de)
PT (1)	PT71326A (de)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU550371B2 (en) *	1981-02-02	1986-03-20	Mobil Oil Corp.	Isomerisation of xylenes and conversion of ethyl benzene to p-xylene
US4443326A (en) *	1981-10-16	1984-04-17	Chevron Research Company	Two-step reforming process
US4429176A (en)	1982-02-08	1984-01-31	Mobil Oil Corporation	Active zeolite catalysts of improved stability
US4469909A (en) *	1982-06-18	1984-09-04	Mobil Oil Corporation	Heavy aromatics process
US5254770A (en) *	1982-09-01	1993-10-19	Mobil Oil Corp.	Isomerization of aromatic compounds over ZSM-22 zeolite
DE3476063D1 (en) *	1983-09-28	1989-02-16	Mobil Oil Corp	Xylene isomerization process
US4594146A (en) *	1983-10-06	1986-06-10	Mobil Oil Corporation	Conversion with zeolite catalysts prepared by steam treatment
US4584423A (en) *	1984-07-30	1986-04-22	Chevron Research Company	Xylene isomerization using a zeolite with a group II metal
US5043512A (en) *	1988-10-06	1991-08-27	Mobil Oil Corp.	Alkylaromatic isomerization process
US5030787A (en) *	1990-01-24	1991-07-09	Mobil Oil Corp.	Catalytic disproportionation/transalkylation utilizing a C9+ aromatics feed
US5349114A (en) *	1993-04-05	1994-09-20	Mobil Oil Corp.	Shape selective hydrocarbon conversions over modified catalyst
US5365004A (en) *	1993-05-28	1994-11-15	Mobil Oil Corp.	Selective toluene disproportionation process (STDP) with ex situ selectivated zeolite catalysts
US5530170A (en) *	1993-05-28	1996-06-25	Mobil Oil Corporation	Ethylbenzene alkylation with ethylene to produce para-diethylbenzene
US5367099A (en) *	1993-05-28	1994-11-22	Mobil Oil Corp.	Selective toluene disproportionation process (STDP) with ex situ selectivated zeolite catalyst
US5476823A (en) *	1993-05-28	1995-12-19	Mobil Oil Corp.	Method of preparation of ex situ selectivated zeolite catalysts for enhanced shape selective applications and method to increase the activity thereof
US5659098A (en) *	1993-05-28	1997-08-19	Beck; Jeffrey S.	High conversion touluene disproportionation with ex situ selectivated zeolite catalysts
US5382737A (en) *	1993-05-28	1995-01-17	Mobil Oil Corp.	Selective ethylbenzene disproportionation process (SEBDP) with ex situ selectivated zeolite catalysts
US5698756A (en) *	1993-05-28	1997-12-16	Mobil Oil Corporation	Toluene alkylation with ethylene to produce para-ethyloluene
US6576582B1 (en)	1993-05-28	2003-06-10	Exxonmobil Oil Corporation	Binderless ex situ selectivated zeolite catalyst
US5403800A (en) *	1993-05-28	1995-04-04	Mobil Oil Corp.	Multiple impregnation technique for the preparation of ex situ selectivated zeolite catalysts
US5406015A (en) *	1993-05-28	1995-04-11	Mobil Oil Corp.	Selective ethylbenzene disproportionation processes (SEBDP) with ex situ selectivated zeolite catalyst
US5396010A (en) *	1993-08-16	1995-03-07	Mobil Oil Corporation	Heavy naphtha upgrading
US5726114A (en) *	1993-10-27	1998-03-10	Mobil Oil Corporation	Method of preparation of ex situ selectivated zeolite catalysts for enhanced shape selective applications and methods to increase the activity thereof
US5625104A (en) *	1995-06-06	1997-04-29	Mobil Oil Corporation	Alkali metal ion exchanged selectivated zeolite catalyst
FR2730728B1 (fr) *	1995-02-21	1997-05-23	Inst Francais Du Petrole	Procede de separation du p-xylene comportant un pretraitement par hydrogenation selective et par de la terre activee
US5849968A (en) *	1995-06-06	1998-12-15	Mobil Oil Corporation	Hydrocarbon conversion process with alkaline earth metal ion exchanged selectivated zeolite catalyst
US5773679A (en) *	1995-12-26	1998-06-30	Mobil Oil Corporation	Performance enhancement of zeolite catalysts with water cofeed
US5945364A (en) *	1996-06-26	1999-08-31	Phillips Petroleum Company	Catalyst composition comprising acid-base leached zeolites
US6518472B1 (en)	1996-08-05	2003-02-11	Bp Corporation North America Inc.	Stabilized dual bed xylene isomerization catalyst system
US6346498B1 (en)	1997-12-19	2002-02-12	Exxonmobil Oil Corporation	Zeolite catalysts having stabilized hydrogenation-dehydrogenation function
US6207871B1 (en)	1997-12-19	2001-03-27	Mobil Oil Corporation	High-purity meta-xylene production process
US5998688A (en) *	1998-08-25	1999-12-07	Mobil Oil Corporation	Xylene isomerization process using toluene co-feed
EP1187890A1 (de) *	1999-05-25	2002-03-20	Exxonmobil Oil Corporation	Vielstufiges reformierverfahren unter verwendung eines rhenium enthaltenden katalysators in der endstufe
US20090093662A1 (en) *	2007-10-08	2009-04-09	Whitchurch Patrick C	Aromatic isomerization catalyst
US7629283B2 (en) *	2007-10-08	2009-12-08	Uop Llc	Aromatic isomerization catalyst and isomerization process
US8840762B2 (en) *	2010-08-25	2014-09-23	Uop Llc	Energy conservation in heavy-hydrocarbon distillation
WO2013085681A1 (en) *	2011-12-06	2013-06-13	Exxonmobil Chemical Patents Inc.	Production process of para -xylene and apparatus thereof
CN112771013B (zh) *	2018-07-20	2024-05-28	Scg化学有限公司	对二甲苯生产的集成方法
US11198822B2 (en) *	2019-04-10	2021-12-14	Exxonmobil Research And Engineering Company	Processes to convert naphtha to heavier products
WO2021041022A1 (en) *	2019-08-23	2021-03-04	Exxonmobil Chemical Patents Inc.	Processes for isomerizing c8 aromatic hydrocarbons using serial reactors

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3856873A (en) *	1973-09-13	1974-12-24	Mobil Oil Corp	Xylene isomerization
US3856871A (en) *	1973-09-13	1974-12-24	Mobil Oil Corp	Xylene isomerization
US3856872A (en) *	1973-09-13	1974-12-24	Mobil Oil Corp	Xylene isomerization
US4100214A (en) *	1976-05-07	1978-07-11	Mobil Oil Corporation	Isomerization of monocyclic alkyl aromatic hydrocarbons
US4101597A (en) *	1977-06-23	1978-07-18	Mobil Oil Corporation	Recovery of p-xylene and benzene from eight carbon atom aromatic fractions
US4163028A (en) *	1977-07-22	1979-07-31	Mobil Oil Corporation	Xylene isomerization

1979
- 1979-05-21 US US06/041,268 patent/US4224141A/en not_active Expired - Lifetime
1980
- 1980-05-12 DE DE8080301536T patent/DE3060723D1/de not_active Expired
- 1980-05-12 AT AT80301536T patent/ATE1417T1/de not_active IP Right Cessation
- 1980-05-12 EP EP80301536A patent/EP0020043B1/de not_active Expired
- 1980-05-20 NO NO801488A patent/NO153004C/no unknown
- 1980-05-20 ES ES491630A patent/ES491630A0/es active Granted
- 1980-05-21 CA CA000352418A patent/CA1147353A/en not_active Expired
- 1980-05-21 HU HU801282A patent/HU184932B/hu not_active IP Right Cessation
- 1980-05-21 AU AU58639/80A patent/AU536713B2/en not_active Ceased
- 1980-05-21 NZ NZ193796A patent/NZ193796A/xx unknown
- 1980-05-21 CS CS803550A patent/CS223832B2/cs unknown
- 1980-05-21 MX MX182438A patent/MX154768A/es unknown
- 1980-05-21 AR AR281156A patent/AR220627A1/es active
- 1980-05-21 JP JP55066564A patent/JPS603368B2/ja not_active Expired
- 1980-05-21 PL PL22438780A patent/PL224387A1/xx unknown
- 1980-05-29 PT PT71326A patent/PT71326A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES8104382A1 (es)	1981-04-01
EP0020043A1 (de)	1980-12-10
ES491630A0 (es)	1981-04-01
JPS603368B2 (ja)	1985-01-28
DE3060723D1 (en)	1982-09-30
AU536713B2 (en)	1984-05-17
NZ193796A (en)	1983-06-14
NO801488L (no)	1980-11-24
JPS5643219A (en)	1981-04-21
EP0020043B1 (de)	1982-08-04
NO153004C (no)	1986-01-02
PT71326A (en)	1980-06-01
NO153004B (no)	1985-09-23
AU5863980A (en)	1980-11-27
ATE1417T1 (de)	1982-08-15
MX154768A (es)	1987-12-11
CA1147353A (en)	1983-05-31
AR220627A1 (es)	1980-11-14
US4224141A (en)	1980-09-23
HU184932B (en)	1984-11-28
PL224387A1 (de)	1981-02-13

Publication	Publication Date	Title
CS223832B2 (en)	1983-11-25	Method of isomeraion of xylene
US4188282A (en)	1980-02-12	Manufacture of benzene, toluene and xylene
US3856873A (en)	1974-12-24	Xylene isomerization
KR101162796B1 (ko)	2012-07-05	여러고리 방향족 화합물의 크실렌으로의 촉매 전환
US3856871A (en)	1974-12-24	Xylene isomerization
CA1181434A (en)	1985-01-22	Manufacture of benzene, toluene and xylene
EP0000812B1 (de)	1981-09-02	Verfahren zur Isomerisierung von Xylenen
EP0021604B1 (de)	1983-01-26	Isomerisierung von Xylol
US3948758A (en)	1976-04-06	Production of alkyl aromatic hydrocarbons
US3957621A (en)	1976-05-18	Production of alkyl aromatic hydrocarbons
DE69705958T2 (de)	2002-04-04	Alkylierungsverfahren in dem zeolith beta verwendet wird
CN101910094B (zh)	2013-09-18	将乙烷或混合低级烷烃转化为芳族烃的方法
EP0234684A1 (de)	1987-09-02	Verfahren zur Isomerisierung von Xylolen
US5028573A (en)	1991-07-02	Dual function catalyst and isomerization therewith
US4211886A (en)	1980-07-08	Manufacture of benzene, toluene and xylene
US4078990A (en)	1978-03-14	Manufacture of lower aromatic compounds
US5004854A (en)	1991-04-02	Pseudocumene and mesitylene production and coproduction thereof with xylene
KR102235872B1 (ko)	2021-04-06	방향족 탄화수소의 메틸화 방법
US3856874A (en)	1974-12-24	Xylene isomerization
US4469909A (en)	1984-09-04	Heavy aromatics process
US4218573A (en)	1980-08-19	Xylene isomerization
US4351979A (en)	1982-09-28	Manufacture of aromatic compounds
US4101596A (en)	1978-07-18	Low pressure xylene isomerization
DE60009729T2 (de)	2005-03-31	Aufwertung von reformaten mit zeolit-katalysatoren
US5082984A (en)	1992-01-21	Dual function catalyst and isomerization therewith