JPH0569105B2 - - Google Patents
Info
- Publication number
- JPH0569105B2 JPH0569105B2 JP60254254A JP25425485A JPH0569105B2 JP H0569105 B2 JPH0569105 B2 JP H0569105B2 JP 60254254 A JP60254254 A JP 60254254A JP 25425485 A JP25425485 A JP 25425485A JP H0569105 B2 JPH0569105 B2 JP H0569105B2
- Authority
- JP
- Japan
- Prior art keywords
- ethanol
- catalyst
- aminophenyl
- reaction
- indoles
- 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
- 239000003054 catalyst Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 17
- 150000002475 indoles Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 13
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- ILDXSRFKXABMHH-UHFFFAOYSA-N 2-(2-aminophenyl)ethanol Chemical compound NC1=CC=CC=C1CCO ILDXSRFKXABMHH-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WBIYLDMSLIXZJK-UHFFFAOYSA-N 1-(2-aminophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1N WBIYLDMSLIXZJK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 150000002476 indolines Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- MVBJKIMHVJZBPW-UHFFFAOYSA-N 1-(2-aminophenyl)-3-methylbutan-2-ol Chemical compound CC(C)C(O)CC1=CC=CC=C1N MVBJKIMHVJZBPW-UHFFFAOYSA-N 0.000 description 1
- XSMIRMRVLNRGDX-UHFFFAOYSA-N 1-(2-aminophenyl)butan-2-ol Chemical compound CCC(O)CC1=CC=CC=C1N XSMIRMRVLNRGDX-UHFFFAOYSA-N 0.000 description 1
- FTQBIKFTBHLHMF-UHFFFAOYSA-N 1-(2-aminophenyl)propan-2-ol Chemical compound CC(O)CC1=CC=CC=C1N FTQBIKFTBHLHMF-UHFFFAOYSA-N 0.000 description 1
- SXDQMIMSGNJPLX-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC(CCO)=C1N SXDQMIMSGNJPLX-UHFFFAOYSA-N 0.000 description 1
- HOCPHZKDNNMZTQ-UHFFFAOYSA-N 2-(2-amino-5-fluorophenyl)ethanol Chemical compound NC1=CC=C(F)C=C1CCO HOCPHZKDNNMZTQ-UHFFFAOYSA-N 0.000 description 1
- KAJZPNVVWSMAEN-UHFFFAOYSA-N 2-(2-amino-5-methoxyphenyl)-1-phenylethanol Chemical compound COC1=CC=C(N)C(CC(O)C=2C=CC=CC=2)=C1 KAJZPNVVWSMAEN-UHFFFAOYSA-N 0.000 description 1
- QENAIVHONFYTNR-UHFFFAOYSA-N 2-(2-amino-5-propan-2-ylphenyl)ethanol Chemical compound CC(C)C1=CC=C(N)C(CCO)=C1 QENAIVHONFYTNR-UHFFFAOYSA-N 0.000 description 1
- UJXDVZGVYQJEPG-UHFFFAOYSA-N 2-(2-amino-5-tert-butylphenyl)ethanol Chemical compound CC(C)(C)C1=CC=C(N)C(CCO)=C1 UJXDVZGVYQJEPG-UHFFFAOYSA-N 0.000 description 1
- QWYTZQOTARHMQU-UHFFFAOYSA-N 2-(2-amino-6-methoxyphenyl)ethanol Chemical compound COC1=CC=CC(N)=C1CCO QWYTZQOTARHMQU-UHFFFAOYSA-N 0.000 description 1
- ZXMUJUDDWIXJRZ-UHFFFAOYSA-N 2-(2-amino-6-phenylmethoxyphenyl)ethanol Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1CCO ZXMUJUDDWIXJRZ-UHFFFAOYSA-N 0.000 description 1
- ISNFKZYQNDRKDK-UHFFFAOYSA-N 2-(2-aminophenyl)-1-cyclohexylethanol Chemical compound NC1=CC=CC=C1CC(O)C1CCCCC1 ISNFKZYQNDRKDK-UHFFFAOYSA-N 0.000 description 1
- DCSDIAAJIWGYBY-UHFFFAOYSA-N 2-(2-aminophenyl)-1-phenylethanol Chemical compound NC1=CC=CC=C1CC(O)C1=CC=CC=C1 DCSDIAAJIWGYBY-UHFFFAOYSA-N 0.000 description 1
- BBHKBHABPOVRMS-UHFFFAOYSA-N 2-(2-aminophenyl)-2-phenylethanol Chemical compound NC1=CC=CC=C1C(CO)C1=CC=CC=C1 BBHKBHABPOVRMS-UHFFFAOYSA-N 0.000 description 1
- WTTUBMVPVATZBZ-UHFFFAOYSA-N 2-(2-aminophenyl)propan-1-ol Chemical compound OCC(C)C1=CC=CC=C1N WTTUBMVPVATZBZ-UHFFFAOYSA-N 0.000 description 1
- OTRBREPTEKIWQV-UHFFFAOYSA-N 4-amino-3-(2-hydroxyethyl)phenol Chemical compound NC1=CC=C(O)C=C1CCO OTRBREPTEKIWQV-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- -1 Cu and Ag Chemical class 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000005001 aminoaryl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Indole Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254254A JPS62114958A (ja) | 1985-11-13 | 1985-11-13 | インド−ル類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254254A JPS62114958A (ja) | 1985-11-13 | 1985-11-13 | インド−ル類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62114958A JPS62114958A (ja) | 1987-05-26 |
| JPH0569105B2 true JPH0569105B2 (enrdf_load_html_response) | 1993-09-30 |
Family
ID=17262425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60254254A Granted JPS62114958A (ja) | 1985-11-13 | 1985-11-13 | インド−ル類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62114958A (enrdf_load_html_response) |
-
1985
- 1985-11-13 JP JP60254254A patent/JPS62114958A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62114958A (ja) | 1987-05-26 |
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