DE2125676C3 - Verfahren zur Isomerisierung von aromatischen C↓8↓ - Kohlenwasserstoffen - Google Patents
Verfahren zur Isomerisierung von aromatischen C↓8↓ - KohlenwasserstoffenInfo
- Publication number
- DE2125676C3 DE2125676C3 DE2125676A DE2125676A DE2125676C3 DE 2125676 C3 DE2125676 C3 DE 2125676C3 DE 2125676 A DE2125676 A DE 2125676A DE 2125676 A DE2125676 A DE 2125676A DE 2125676 C3 DE2125676 C3 DE 2125676C3
- Authority
- DE
- Germany
- Prior art keywords
- isomerization
- hydrocarbons
- percent
- hydrogen
- mixture
- 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
- 238000006317 isomerization reaction Methods 0.000 title claims description 40
- 229930195733 hydrocarbon Natural products 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 26
- 125000003118 aryl group Chemical group 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 claims description 32
- 150000002430 hydrocarbons Chemical class 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 230000000737 periodic effect Effects 0.000 claims description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 46
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 23
- 238000002474 experimental method Methods 0.000 description 21
- 239000007789 gas Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 229940078552 o-xylene Drugs 0.000 description 6
- 150000003738 xylenes Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001833 catalytic reforming Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- -1 fluorine Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 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
- 101150063042 NR0B1 gene Proteins 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 229910021486 amorphous silicon dioxide Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 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
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
-
- 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
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/2724—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25091/70A GB1255459A (en) | 1970-05-26 | 1970-05-26 | Process for the isomerization of alkylaromatic hydrocarbons |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2125676A1 DE2125676A1 (de) | 1971-12-02 |
| DE2125676B2 DE2125676B2 (de) | 1981-06-19 |
| DE2125676C3 true DE2125676C3 (de) | 1982-04-29 |
Family
ID=10222060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2125676A Expired DE2125676C3 (de) | 1970-05-26 | 1971-05-24 | Verfahren zur Isomerisierung von aromatischen C↓8↓ - Kohlenwasserstoffen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE767243A (OSRAM) |
| CA (1) | CA960700A (OSRAM) |
| DE (1) | DE2125676C3 (OSRAM) |
| ES (1) | ES391481A1 (OSRAM) |
| FR (1) | FR2093630A5 (OSRAM) |
| GB (1) | GB1255459A (OSRAM) |
| NL (1) | NL169990C (OSRAM) |
| SE (1) | SE373121B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6512155B1 (en) | 2000-04-25 | 2003-01-28 | Uop Llc | Process for the activation of an alkylaromatic isomerization catalyst by water |
| AU2003303863A1 (en) * | 2003-01-27 | 2004-08-30 | Uop Llc | Process for the activation of an alkylaromatic isomerization catalyst by water |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE848803C (de) * | 1950-01-09 | 1952-09-08 | Bataafsche Petroleum | Verfahren zum Isomerisieren von Xylolen |
| GB930092A (en) * | 1960-07-21 | 1963-07-03 | Ici Ltd | Improvements in and relating to xylene isomerisation processes |
| GB962871A (en) * | 1961-10-30 | 1964-07-08 | Maruzen Oil Company Ltd | A process for the isomerization of xylenes |
| US3381048A (en) * | 1965-09-16 | 1968-04-30 | Standard Oil Co | Isomerization of xylene isomers |
| GB1171865A (en) * | 1967-10-19 | 1969-11-26 | Shell Int Research | Continuous Process for the Preparation of p-Xylene. |
-
1970
- 1970-05-26 GB GB25091/70A patent/GB1255459A/en not_active Expired
-
1971
- 1971-05-17 BE BE767243A patent/BE767243A/nl not_active IP Right Cessation
- 1971-05-21 CA CA113,678A patent/CA960700A/en not_active Expired
- 1971-05-24 NL NLAANVRAGE7107053,A patent/NL169990C/xx not_active IP Right Cessation
- 1971-05-24 DE DE2125676A patent/DE2125676C3/de not_active Expired
- 1971-05-24 FR FR7118586A patent/FR2093630A5/fr not_active Expired
- 1971-05-24 SE SE7106688A patent/SE373121B/xx unknown
- 1971-05-24 ES ES391481A patent/ES391481A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL169990C (nl) | 1982-09-16 |
| ES391481A1 (es) | 1973-06-16 |
| NL7107053A (OSRAM) | 1971-11-30 |
| CA960700A (en) | 1975-01-07 |
| BE767243A (nl) | 1971-11-17 |
| DE2125676A1 (de) | 1971-12-02 |
| NL169990B (nl) | 1982-04-16 |
| SE373121B (OSRAM) | 1975-01-27 |
| DE2125676B2 (de) | 1981-06-19 |
| FR2093630A5 (OSRAM) | 1972-01-28 |
| GB1255459A (en) | 1971-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2526887C2 (de) | Verfahren zur Herstellung von aromatischen Kohlenwasserstoffen | |
| EP0714872B1 (de) | Katalysator für die Dehydrierung von C6-bis C15-Paraffinen | |
| DE2107568C3 (de) | Verfahren zur Reinigung von Kohlenwasserstoffen durch selektive Hydrierung | |
| DE2419620C3 (de) | Verfahren zur Herstellung von Adamantan und seinen Derivaten | |
| DE3441072A1 (de) | Verfahren zur herstellung von cyclischen alkoholen | |
| EP0411455B1 (de) | Verfahren zur kontinuierlichen Reinigung von Caprolactam | |
| DE2148121A1 (de) | Verfahren zum katalytischen Cracken von Naphtha | |
| EP0129900B1 (de) | Verfahren zur Gewinnung von 1-Buten aus 2-Butene enthaltenden C4-Kohlenwasserstoffgemischen | |
| DE3427979A1 (de) | Verfahren zur gewinnung von 2-butenen aus 1-buten und gegebenenfalls 2-butene enthaltenden c(pfeil abwaerts)4(pfeil abwaerts)-kohlenwasserstoffgemischen | |
| DE69417607T2 (de) | Verfahren zur Herstellung von Benzin mit hoher Oktanzahl | |
| DE68924855T2 (de) | Herstellung eines Hydrobehandlungskatalysators. | |
| DE69505193T2 (de) | Verfahren zur Verjüngung eines festen Alkylierungskatalysators | |
| DE2125676C3 (de) | Verfahren zur Isomerisierung von aromatischen C↓8↓ - Kohlenwasserstoffen | |
| EP0206143A1 (de) | Verfahren zur Herstellung von 4-Pentensäureestern | |
| DE2751888A1 (de) | Verfahren zur herstellung eines hydroalkylierungskatalysators | |
| EP1169285A1 (de) | Verfahren zur hydrierung von unsubstituierten oder alkylsubstituierten aromaten unter verwendung eines makroporen aufweisenden katalysators | |
| EP0352505B1 (de) | Verfahren zur Herstellung von Thymol | |
| DE69400225T2 (de) | Verfahren zur Isomerisierung von Dimethylnaphthalen | |
| DE2620854B2 (de) | Verfahren zur Trennung eines Reaktionsproduktgemisches, das Wasserstoff, gasförmige und flüssige Kohlenwasserstoffe enthält | |
| DE69001702T2 (de) | Katalysatorzusammensetzung, Verfahren zum Kracken von Nichtaromaten und Verfahren zum Isomerisieren von C8-aromatischen Kohlenwasserstoffen. | |
| DE2030724C3 (de) | Verfahren zum Hydrieren von Benzol zu Cyclohexan | |
| DE2720456A1 (de) | Verfahren zur isomerisierung von isopropylnaphthalin | |
| DE69022879T2 (de) | Verfahren zur Isomerisierung von Kohlenwasserstoffen. | |
| DE60003775T2 (de) | Verfahren und Vorrichtung zur Alkylierung von Isobutan mittels leichten Olefinen | |
| EP0199209B1 (de) | Verfahren zur Herstellung von Alkylbenzolen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |