DE1770977A1 - Verfahren zur katalytischen Dehydrierung von 2,3-Dihydroindol - Google Patents
Verfahren zur katalytischen Dehydrierung von 2,3-DihydroindolInfo
- Publication number
- DE1770977A1 DE1770977A1 DE19681770977 DE1770977A DE1770977A1 DE 1770977 A1 DE1770977 A1 DE 1770977A1 DE 19681770977 DE19681770977 DE 19681770977 DE 1770977 A DE1770977 A DE 1770977A DE 1770977 A1 DE1770977 A1 DE 1770977A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydroindole
- catalyst
- organic solvent
- reaction
- inert organic
- 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.)
- Pending
Links
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 14
- 238000006356 dehydrogenation reaction Methods 0.000 title claims description 7
- 230000003197 catalytic effect Effects 0.000 title claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 4
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 18
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000370 acceptor Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FXEDRSGUZBCDMO-PHEQNACWSA-N [(e)-3-phenylprop-2-enoyl] (e)-3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OC(=O)\C=C\C1=CC=CC=C1 FXEDRSGUZBCDMO-PHEQNACWSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE11119/67A SE327988B (enExample) | 1967-08-04 | 1967-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770977A1 true DE1770977A1 (de) | 1972-01-13 |
Family
ID=20293380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770977 Pending DE1770977A1 (de) | 1967-08-04 | 1968-07-25 | Verfahren zur katalytischen Dehydrierung von 2,3-Dihydroindol |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3558663A (enExample) |
| DE (1) | DE1770977A1 (enExample) |
| FR (1) | FR1576807A (enExample) |
| GB (1) | GB1193764A (enExample) |
| SE (1) | SE327988B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3035403C2 (de) * | 1980-09-19 | 1982-08-26 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur Herstellung von 5-Chlorindol |
| CN111187196B (zh) * | 2018-11-15 | 2023-05-30 | 有限会社佐藤企画 | 焦油系吲哚的纯化方法 |
-
1967
- 1967-08-04 SE SE11119/67A patent/SE327988B/xx unknown
-
1968
- 1968-07-23 GB GB35174/68A patent/GB1193764A/en not_active Expired
- 1968-07-24 US US747081A patent/US3558663A/en not_active Expired - Lifetime
- 1968-07-25 DE DE19681770977 patent/DE1770977A1/de active Pending
- 1968-08-02 FR FR1576807D patent/FR1576807A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1576807A (enExample) | 1969-08-01 |
| SE327988B (enExample) | 1970-09-07 |
| US3558663A (en) | 1971-01-26 |
| GB1193764A (en) | 1970-06-03 |
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