JPS5655366A - Preparation of indoles - Google Patents
Preparation of indolesInfo
- Publication number
- JPS5655366A JPS5655366A JP13178479A JP13178479A JPS5655366A JP S5655366 A JPS5655366 A JP S5655366A JP 13178479 A JP13178479 A JP 13178479A JP 13178479 A JP13178479 A JP 13178479A JP S5655366 A JPS5655366 A JP S5655366A
- Authority
- JP
- Japan
- Prior art keywords
- copper
- anilines
- aniline
- catalyst
- ethylene glycol
- 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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Natural products 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C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract 4
- 150000002475 indoles Chemical class 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound 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OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound 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[Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 3
- 229910052802 copper Inorganic materials 0.000 abstract 3
- 239000010949 copper Substances 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound 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NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001448 anilines Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000010574 gas phase reaction Methods 0.000 abstract 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound 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NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 1
- 239000005751 Copper oxide Substances 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound 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[Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 1
- 229910000431 copper oxide Inorganic materials 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound data:image/svg+xml;base64,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 data:image/svg+xml;base64,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 C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound 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CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
Abstract
PURPOSE: To prepare indoles useful as a synthetic raw material of perfumery and amino acids, in one step, with low production of by-products, in high selectivity, by the gas phase reaction of anilines and ethylene glycol available at low costs in the presence of a copper-containing catalyst.
CONSTITUTION: Indole or its derivative is prepared by the gas-phase reaction of anilines (e.g. aniline, p-toluidine, p-aminophenol, etc.) with ethylene glycol in the presence of a copper-containing catalyst (e.g. metallic copper, copper oxide, etc.) at 200W500°C, pref.250W400°C. The amount of ethylene gylcol is 0.01W5mol/mol of aniline.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54131784A JPS6320224B2 (en) | 1979-10-15 | 1979-10-15 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54131784A JPS6320224B2 (en) | 1979-10-15 | 1979-10-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5655366A true JPS5655366A (en) | 1981-05-15 |
| JPS6320224B2 JPS6320224B2 (en) | 1988-04-26 |
Family
ID=15066059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54131784A Expired JPS6320224B2 (en) | 1979-10-15 | 1979-10-15 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6320224B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829762A (en) * | 1981-08-18 | 1983-02-22 | Mitsui Toatsu Chem Inc | Preparation of indole |
| WO1983000691A1 (en) * | 1981-08-25 | 1983-03-03 | Honda, Tadatoshi | Improved process for preparing indole |
| JPS58225061A (en) * | 1982-06-24 | 1983-12-27 | Mitsui Toatsu Chem Inc | Preparation of indole compound |
| JPS5955869A (en) * | 1982-09-22 | 1984-03-31 | Mitsui Toatsu Chem Inc | Preparation of indole compound |
| US4443615A (en) * | 1981-11-10 | 1984-04-17 | Tanabe Seiyaku Co., Ltd. | Process for preparing indoles |
| JPS61115066A (en) * | 1984-11-12 | 1986-06-02 | Mitsui Toatsu Chem Inc | Production of indole |
| JPH01121264A (en) * | 1987-11-06 | 1989-05-12 | Mitsui Toatsu Chem Inc | Production of indoles |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5636451A (en) * | 1979-09-04 | 1981-04-09 | Ube Ind Ltd | Production of indole |
-
1979
- 1979-10-15 JP JP54131784A patent/JPS6320224B2/ja not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5636451A (en) * | 1979-09-04 | 1981-04-09 | Ube Ind Ltd | Production of indole |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829762A (en) * | 1981-08-18 | 1983-02-22 | Mitsui Toatsu Chem Inc | Preparation of indole |
| JPH0432065B2 (en) * | 1981-08-18 | 1992-05-28 | ||
| WO1983000691A1 (en) * | 1981-08-25 | 1983-03-03 | Honda, Tadatoshi | Improved process for preparing indole |
| US4443615A (en) * | 1981-11-10 | 1984-04-17 | Tanabe Seiyaku Co., Ltd. | Process for preparing indoles |
| JPS58225061A (en) * | 1982-06-24 | 1983-12-27 | Mitsui Toatsu Chem Inc | Preparation of indole compound |
| US4937353A (en) * | 1982-06-24 | 1990-06-26 | Mitsui Toatsu Chemicals, Incorporated | Preparation process for indoles |
| JPH0359064B2 (en) * | 1982-06-24 | 1991-09-09 | Mitsui Toatsu Chemicals | |
| JPS5955869A (en) * | 1982-09-22 | 1984-03-31 | Mitsui Toatsu Chem Inc | Preparation of indole compound |
| JPH0347263B2 (en) * | 1982-09-22 | 1991-07-18 | Mitsui Toatsu Chemicals | |
| JPH0347264B2 (en) * | 1984-11-12 | 1991-07-18 | Mitsui Toatsu Chemicals | |
| JPS61115066A (en) * | 1984-11-12 | 1986-06-02 | Mitsui Toatsu Chem Inc | Production of indole |
| JPH01121264A (en) * | 1987-11-06 | 1989-05-12 | Mitsui Toatsu Chem Inc | Production of indoles |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6320224B2 (en) | 1988-04-26 |
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