DE2052678C3 - Verfahren zur Herstellung von Indol - Google Patents
Verfahren zur Herstellung von IndolInfo
- Publication number
- DE2052678C3 DE2052678C3 DE2052678A DE2052678A DE2052678C3 DE 2052678 C3 DE2052678 C3 DE 2052678C3 DE 2052678 A DE2052678 A DE 2052678A DE 2052678 A DE2052678 A DE 2052678A DE 2052678 C3 DE2052678 C3 DE 2052678C3
- Authority
- DE
- Germany
- Prior art keywords
- indole
- gas
- catalyst
- mixture
- reducing gas
- 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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 30
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims description 15
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 15
- 239000007789 gas Substances 0.000 claims description 19
- 239000010949 copper Substances 0.000 claims description 16
- 229910052802 copper Inorganic materials 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- SLRIOXRBAPBGEI-UHFFFAOYSA-N 2-(2-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC=C1[N+]([O-])=O SLRIOXRBAPBGEI-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 2
- 235000011151 potassium sulphates Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- DSDBYQDNNWCLHL-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1[N+]([O-])=O DSDBYQDNNWCLHL-UHFFFAOYSA-N 0.000 description 1
- PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006063 cullet Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE14902/69A SE344589B (enExample) | 1969-10-30 | 1969-10-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2052678A1 DE2052678A1 (de) | 1971-05-06 |
| DE2052678B2 DE2052678B2 (de) | 1975-03-13 |
| DE2052678C3 true DE2052678C3 (de) | 1975-10-23 |
Family
ID=20299857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2052678A Expired DE2052678C3 (de) | 1969-10-30 | 1970-10-27 | Verfahren zur Herstellung von Indol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3699120A (enExample) |
| JP (1) | JPS4920778B1 (enExample) |
| DE (1) | DE2052678C3 (enExample) |
| FR (1) | FR2066678A5 (enExample) |
| GB (1) | GB1282660A (enExample) |
| SE (1) | SE344589B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS607619B2 (ja) * | 1976-01-07 | 1985-02-26 | 三井化学株式会社 | インドール類の製造方法 |
| JPS56150062A (en) * | 1980-04-22 | 1981-11-20 | Mitsui Toatsu Chem Inc | Production of indole or indole derivative |
| JPS5923306B2 (ja) | 1980-06-03 | 1984-06-01 | 三井東圧化学株式会社 | インド−ルまたはインド−ル誘導体の製造方法 |
| US4436917A (en) | 1981-04-15 | 1984-03-13 | Mitsui Toatsu Chemicals, Inc. | Process for the preparation of indoles |
| US4376205A (en) * | 1981-04-15 | 1983-03-08 | Mitsui Toatsu Chemicals, Inc. | Process for the preparation of indoles from anilines and ethanolamines |
| US4456760A (en) * | 1981-04-15 | 1984-06-26 | Mitsui Toatsu Chemicals, Incorporated | Process for the preparation of indoles |
| JPS61118361A (ja) * | 1984-11-12 | 1986-06-05 | Res Assoc Util Of Light Oil | インド−ル類の製造方法 |
| US5332838A (en) * | 1988-03-29 | 1994-07-26 | Amoco Corporation | Cyclization process utilizing copper aluminum borate as a catalyst |
-
1969
- 1969-10-30 SE SE14902/69A patent/SE344589B/xx unknown
-
1970
- 1970-10-14 GB GB48871/70A patent/GB1282660A/en not_active Expired
- 1970-10-27 DE DE2052678A patent/DE2052678C3/de not_active Expired
- 1970-10-28 US US84881A patent/US3699120A/en not_active Expired - Lifetime
- 1970-10-28 FR FR7038927A patent/FR2066678A5/fr not_active Expired
- 1970-10-29 JP JP45095532A patent/JPS4920778B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4920778B1 (enExample) | 1974-05-27 |
| SE344589B (enExample) | 1972-04-24 |
| FR2066678A5 (enExample) | 1971-08-06 |
| US3699120A (en) | 1972-10-17 |
| GB1282660A (en) | 1972-07-19 |
| DE2052678A1 (de) | 1971-05-06 |
| DE2052678B2 (de) | 1975-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2732952C2 (de) | Verfahren zur Herstellung von Methacrylderivaten aus tert.-Butylgruppen enthaltenden Verbindungen | |
| DE2052678C3 (de) | Verfahren zur Herstellung von Indol | |
| DE2441109A1 (de) | Verfahren zur katalytischen oxydation von tert.-butylalkohol in der dampfphase | |
| EP0726092B1 (de) | Verfahren zur Herstellung von Cyanopyridinen und dafür geeignete Katalysatoren | |
| DE3244032A1 (de) | Verfahren zur herstellung von pyridin | |
| EP0059414A2 (de) | Katalysatoren für die Herstellung von 3-Cyanpyridin | |
| DE2703070A1 (de) | Verfahren zur herstellung von 3-methylpyridin | |
| CH631705A5 (de) | Verfahren zur herstellung substituierter pyridine. | |
| DE2703049C2 (de) | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin | |
| EP1284926B1 (de) | Verfahren zum katalytischen umsetzen von gasen mit hohem gehalt an schwefeldioxid | |
| EP0402727B1 (de) | Verfahren zur Herstellung eines Eisenkatalysators und ein Verfahren zur Herstellung von primären Aminen durch Hydrierung von Nitrilen unter Verwendung dieses Eisenkatalysators | |
| DE2125132C3 (de) | Verfahren zur Herstellung von o-Amino benzonitril | |
| DE1493290A1 (de) | Verfahren zur Herstellung von ungesaettigten Nitrilen | |
| EP0416279A1 (de) | Verfahren zur Herstellung von Kresolisomergemischen mit einem Molverhältnis von para- zu meta-Kresol von mindestens 0,6:1 bis 10:1 | |
| DE2703069A1 (de) | Verfahren zur herstellung von 2-methylpyridin und 3-methylpyridin | |
| CH314000A (de) | Verfahren zur Herstellung von Nitrilen von Verbindungen aromatischen Charakters | |
| DE1964786C3 (de) | Verfahren zur Herstellung von Acrylnitril aus Propan | |
| DE2712694C2 (enExample) | ||
| DE19646131C1 (de) | Verfahren zur Herstellung eines vollmetallischen Katalysators | |
| DE1024080B (de) | Verfahren zur katalytischen Dehydrierung von Piperidin zu Pyridin | |
| DE1143497B (de) | Verfahren zur Herstellung von Blausaeure | |
| DE2056344C3 (de) | Verfahren zur Herstellung von e-Caprolactam | |
| DE1470143C (de) | Verfahren zur Herstellung von 2 Chlor pyndin | |
| DE2813528C3 (de) | Verfahren zur Herstellung von Harnstoff | |
| AT71168B (de) | Verfahren zur Darstellung aromatischer Amine. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |