JPH0427230B2 - - Google Patents
Info
- Publication number
- JPH0427230B2 JPH0427230B2 JP10995586A JP10995586A JPH0427230B2 JP H0427230 B2 JPH0427230 B2 JP H0427230B2 JP 10995586 A JP10995586 A JP 10995586A JP 10995586 A JP10995586 A JP 10995586A JP H0427230 B2 JPH0427230 B2 JP H0427230B2
- Authority
- JP
- Japan
- Prior art keywords
- indole
- oligomer
- salt
- alcohol
- separated
- 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 claims description 247
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 126
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 126
- 150000003839 salts Chemical class 0.000 claims description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 description 25
- 229910000039 hydrogen halide Inorganic materials 0.000 description 17
- 239000012433 hydrogen halide Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 238000011084 recovery Methods 0.000 description 16
- 239000011280 coal tar Substances 0.000 description 13
- 238000005979 thermal decomposition reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- -1 indole alkali salt Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 150000002475 indoles Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10995586A JPS62265261A (ja) | 1986-05-14 | 1986-05-14 | インド−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10995586A JPS62265261A (ja) | 1986-05-14 | 1986-05-14 | インド−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62265261A JPS62265261A (ja) | 1987-11-18 |
| JPH0427230B2 true JPH0427230B2 (enrdf_load_stackoverflow) | 1992-05-11 |
Family
ID=14523367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10995586A Granted JPS62265261A (ja) | 1986-05-14 | 1986-05-14 | インド−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62265261A (enrdf_load_stackoverflow) |
-
1986
- 1986-05-14 JP JP10995586A patent/JPS62265261A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62265261A (ja) | 1987-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4578368A (en) | Catalyst recovery process | |
| JPH0427230B2 (enrdf_load_stackoverflow) | ||
| JP4000721B2 (ja) | ２，２，６，６−テトラメチル−４−オキソピペリジンの製造方法 | |
| US4496760A (en) | Process of decomposition of a complex of ortho-benzoyl benzoic acid, hydrogen fluoride and boron trifluoride | |
| JPS6210491B2 (enrdf_load_stackoverflow) | ||
| JPH0427228B2 (enrdf_load_stackoverflow) | ||
| JPS63156769A (ja) | インド−ルの製造方法 | |
| JPH02149558A (ja) | インドールの回収方法 | |
| JP3001097B1 (ja) | ソルビン酸の製造法 | |
| JPH0518825B2 (enrdf_load_stackoverflow) | ||
| JPS62249968A (ja) | インド−ルの回収方法 | |
| JP3657635B2 (ja) | メチルナフタレンの製造方法 | |
| JP3157724B2 (ja) | インドールの精製方法 | |
| JPH02142769A (ja) | インドールの回収方法 | |
| JPS626537B2 (enrdf_load_stackoverflow) | ||
| JP2874281B2 (ja) | ビフェニル―４，４’―ジオールの分離精製方法 | |
| US3663546A (en) | Process for the preparation of pyridazone derivatives | |
| SU480688A1 (ru) | Способ выделени конденсированных ароматических углеводородов | |
| JPS61167633A (ja) | アリルアルコ−ルの精製方法 | |
| JP3184645B2 (ja) | ４−ハロジフルオロメトキシネオフィル３−フェノキシベンジルエーテル類の改良された精製方法 | |
| JPS5943945B2 (ja) | ε↓−カプロラクタムの精製方法 | |
| JP2571089B2 (ja) | クエン酸とイソクエン酸との分離方法 | |
| JP2537099B2 (ja) | ６―メチルアミノピリジン誘導体の製造方法 | |
| JPS6277365A (ja) | 高純度インド−ルの回収方法 | |
| CN115745768A (zh) | 一种纯化六氯丙酮的方法 |