JPH0518825B2 - - Google Patents
Info
- Publication number
- JPH0518825B2 JPH0518825B2 JP30587686A JP30587686A JPH0518825B2 JP H0518825 B2 JPH0518825 B2 JP H0518825B2 JP 30587686 A JP30587686 A JP 30587686A JP 30587686 A JP30587686 A JP 30587686A JP H0518825 B2 JPH0518825 B2 JP H0518825B2
- Authority
- JP
- Japan
- Prior art keywords
- indole
- oligomer
- salt
- separated
- hydrogen halide
- 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 - Lifetime
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 248
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 125
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 125
- 150000003839 salts Chemical class 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 23
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 229910000039 hydrogen halide Inorganic materials 0.000 description 28
- 239000012433 hydrogen halide Substances 0.000 description 28
- 239000003921 oil Substances 0.000 description 20
- 239000011280 coal tar Substances 0.000 description 13
- 238000011084 recovery Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005979 thermal decomposition reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- -1 indole alkali salt Chemical class 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 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
- 150000004996 alkyl benzenes Chemical class 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
- 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
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum 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
- 230000036632 reaction speed Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30587686A JPS63156770A (ja) | 1986-12-22 | 1986-12-22 | インド−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30587686A JPS63156770A (ja) | 1986-12-22 | 1986-12-22 | インド−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63156770A JPS63156770A (ja) | 1988-06-29 |
| JPH0518825B2 true JPH0518825B2 (enrdf_load_stackoverflow) | 1993-03-15 |
Family
ID=17950401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30587686A Granted JPS63156770A (ja) | 1986-12-22 | 1986-12-22 | インド−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63156770A (enrdf_load_stackoverflow) |
-
1986
- 1986-12-22 JP JP30587686A patent/JPS63156770A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63156770A (ja) | 1988-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0120145B2 (enrdf_load_stackoverflow) | ||
| JPH0518825B2 (enrdf_load_stackoverflow) | ||
| JPH0427228B2 (enrdf_load_stackoverflow) | ||
| JPS6210491B2 (enrdf_load_stackoverflow) | ||
| US3679751A (en) | Boric acid recovery | |
| JPS63156769A (ja) | インド−ルの製造方法 | |
| JPH0427229B2 (enrdf_load_stackoverflow) | ||
| US5059742A (en) | Process for separating 2,6-dimethylnaphthalene | |
| JPH0427230B2 (enrdf_load_stackoverflow) | ||
| US4510099A (en) | Process for preparing pure diacetonitrile | |
| JPS6183142A (ja) | スクアル酸を単離する方法 | |
| US4940832A (en) | Process for separating 2,6-dimethylnaphthalene | |
| JP3657635B2 (ja) | メチルナフタレンの製造方法 | |
| JPH02149558A (ja) | インドールの回収方法 | |
| JPH02142769A (ja) | インドールの回収方法 | |
| JPS6150942B2 (enrdf_load_stackoverflow) | ||
| JPH1077265A (ja) | インドールの精製方法 | |
| JP2537099B2 (ja) | ６―メチルアミノピリジン誘導体の製造方法 | |
| JPH0334970A (ja) | イソキノリンの精製方法 | |
| JPH04312574A (ja) | ２，６−ルチジンの分離精製方法 | |
| JPH02204419A (ja) | ２，６―ジイソプロピルナフタレンの回収方法 | |
| JP2721247B2 (ja) | 精製インドールの製造方法 | |
| JPS61129144A (ja) | ｍ−クレゾ−ルの分離法 | |
| JPS58188854A (ja) | ベンゼンチオ−ル類の改良製法 | |
| JPH0124770B2 (enrdf_load_stackoverflow) |