DE2337951C2 - Verfahren zur Herstellung von 4-Amino-2,5-dialkoxybenzonitrilen - Google Patents
Verfahren zur Herstellung von 4-Amino-2,5-dialkoxybenzonitrilenInfo
- Publication number
- DE2337951C2 DE2337951C2 DE2337951A DE2337951A DE2337951C2 DE 2337951 C2 DE2337951 C2 DE 2337951C2 DE 2337951 A DE2337951 A DE 2337951A DE 2337951 A DE2337951 A DE 2337951A DE 2337951 C2 DE2337951 C2 DE 2337951C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- cyanide
- amino
- acylamino
- 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
- 238000000034 method Methods 0.000 title claims 9
- 238000002360 preparation method Methods 0.000 title claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 239000007800 oxidant agent Substances 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 2
- 229910052979 sodium sulfide Inorganic materials 0.000 claims 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 239000002351 wastewater Substances 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims 1
- HWAMEJIMXIXLIH-UHFFFAOYSA-N 2,5-dimethoxybenzonitrile Chemical compound COC1=CC=C(OC)C(C#N)=C1 HWAMEJIMXIXLIH-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000005749 Copper compound Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000005666 Myers alkylation reaction Methods 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 208000000260 Warts Diseases 0.000 claims 1
- IYEFUCDLTRBVCN-UHFFFAOYSA-N [Br].BrC1=CC=CC=C1 Chemical compound [Br].BrC1=CC=CC=C1 IYEFUCDLTRBVCN-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000011260 aqueous acid Substances 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 150000008359 benzonitriles Chemical class 0.000 claims 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001880 copper compounds Chemical class 0.000 claims 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 1
- 238000001784 detoxification Methods 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000012954 diazonium Substances 0.000 claims 1
- 150000001989 diazonium salts Chemical class 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- -1 formamide Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 201000010153 skin papilloma Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FSTPMFASNVISBU-UHFFFAOYSA-N 2-methoxybenzonitrile Chemical compound COC1=CC=CC=C1C#N FSTPMFASNVISBU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2337951A DE2337951C2 (de) | 1973-07-26 | 1973-07-26 | Verfahren zur Herstellung von 4-Amino-2,5-dialkoxybenzonitrilen |
| US05/490,414 US3933887A (en) | 1973-07-26 | 1974-07-22 | Process for preparing 4-amino-2,5-dialkoxybenzonitriles |
| CH1017274A CH605692A5 (cg-RX-API-DMAC7.html) | 1973-07-26 | 1974-07-23 | |
| JP49084682A JPS5069041A (cg-RX-API-DMAC7.html) | 1973-07-26 | 1974-07-25 | |
| FR7426069A FR2245621B1 (cg-RX-API-DMAC7.html) | 1973-07-26 | 1974-07-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2337951A DE2337951C2 (de) | 1973-07-26 | 1973-07-26 | Verfahren zur Herstellung von 4-Amino-2,5-dialkoxybenzonitrilen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2337951A1 DE2337951A1 (de) | 1975-02-13 |
| DE2337951C2 true DE2337951C2 (de) | 1984-07-26 |
Family
ID=5888028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2337951A Expired DE2337951C2 (de) | 1973-07-26 | 1973-07-26 | Verfahren zur Herstellung von 4-Amino-2,5-dialkoxybenzonitrilen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3933887A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5069041A (cg-RX-API-DMAC7.html) |
| CH (1) | CH605692A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2337951C2 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2245621B1 (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3414628C1 (de) * | 1984-04-18 | 1985-06-27 | Dr. Karl Thomae Gmbh, 7950 Biberach | Verfahren zur Herstellung von 3-Cyano-4-aminoacetophenonen |
| US4900859A (en) * | 1987-12-03 | 1990-02-13 | Hoffman-La Roche Inc. | Process for 4-dimethylamino-3,5-dimethoxybenzaldehyde |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH416662A (de) * | 1962-12-21 | 1966-07-15 | Sandoz Ag | Verfahren zur Herstellung von 1-Acylacetylamino-2,5-dialkoxy-4-brombenzolen |
| US3423412A (en) * | 1966-11-21 | 1969-01-21 | Edward C Taylor | Benzopyrroloquinazolinones |
| DE2137719A1 (de) * | 1971-07-28 | 1973-02-08 | Basf Ag | Verfahren zur herstellung von aminobenzonitrilen |
-
1973
- 1973-07-26 DE DE2337951A patent/DE2337951C2/de not_active Expired
-
1974
- 1974-07-22 US US05/490,414 patent/US3933887A/en not_active Expired - Lifetime
- 1974-07-23 CH CH1017274A patent/CH605692A5/xx not_active IP Right Cessation
- 1974-07-25 JP JP49084682A patent/JPS5069041A/ja active Pending
- 1974-07-26 FR FR7426069A patent/FR2245621B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2245621A1 (cg-RX-API-DMAC7.html) | 1975-04-25 |
| FR2245621B1 (cg-RX-API-DMAC7.html) | 1978-01-20 |
| DE2337951A1 (de) | 1975-02-13 |
| JPS5069041A (cg-RX-API-DMAC7.html) | 1975-06-09 |
| CH605692A5 (cg-RX-API-DMAC7.html) | 1978-10-13 |
| US3933887A (en) | 1976-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07C121/80 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |