DE2132961C3 - Verfahren zur Herstellung von N-Alkytcarbazolen - Google Patents
Verfahren zur Herstellung von N-AlkytcarbazolenInfo
- Publication number
- DE2132961C3 DE2132961C3 DE19712132961 DE2132961A DE2132961C3 DE 2132961 C3 DE2132961 C3 DE 2132961C3 DE 19712132961 DE19712132961 DE 19712132961 DE 2132961 A DE2132961 A DE 2132961A DE 2132961 C3 DE2132961 C3 DE 2132961C3
- Authority
- DE
- Germany
- Prior art keywords
- carbazole
- potassium
- water
- production
- mol
- 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 12
- 150000001716 carbazoles Chemical class 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 15
- WFTICIXFISZPCW-UHFFFAOYSA-N 9h-carbazole;potassium Chemical compound [K].C1=CC=C2C3=CC=CC=C3NC2=C1 WFTICIXFISZPCW-UHFFFAOYSA-N 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims 5
- 229940008406 diethyl sulfate Drugs 0.000 claims 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- 150000003254 radicals Chemical group 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 230000029936 alkylation Effects 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 3
- 239000000543 intermediate Substances 0.000 claims 3
- -1 nitro, cyano, methoxy Chemical group 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000007717 exclusion Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- WONHLSYSHMRRGO-UHFFFAOYSA-N 9-ethyl-3-nitrocarbazole Chemical compound [O-][N+](=O)C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 WONHLSYSHMRRGO-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229940117389 dichlorobenzene Drugs 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229960003750 ethyl chloride Drugs 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000001256 steam distillation Methods 0.000 claims 1
- 239000002351 wastewater Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712132961 DE2132961C3 (de) | 1971-07-02 | 1971-07-02 | Verfahren zur Herstellung von N-Alkytcarbazolen |
| GB3051672A GB1338885A (en) | 1971-07-02 | 1972-06-29 | Process for the preparation of n-alkyl-carbazoles |
| CH978572A CH574927A5 (cg-RX-API-DMAC7.html) | 1971-07-02 | 1972-06-29 | |
| IT2648372A IT963103B (it) | 1971-07-02 | 1972-06-30 | Procedimento per la preparazione di n alchilcarbazoli |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712132961 DE2132961C3 (de) | 1971-07-02 | 1971-07-02 | Verfahren zur Herstellung von N-Alkytcarbazolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2132961A1 DE2132961A1 (de) | 1973-01-11 |
| DE2132961B2 DE2132961B2 (de) | 1975-03-06 |
| DE2132961C3 true DE2132961C3 (de) | 1975-10-23 |
Family
ID=5812492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712132961 Expired DE2132961C3 (de) | 1971-07-02 | 1971-07-02 | Verfahren zur Herstellung von N-Alkytcarbazolen |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH574927A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2132961C3 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1338885A (cg-RX-API-DMAC7.html) |
| IT (1) | IT963103B (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4324707C1 (de) * | 1993-07-23 | 1994-08-25 | Cassella Ag | Verfahren zur Herstellung von N-Ethylcarbazol |
| JP5754678B2 (ja) | 2009-08-24 | 2015-07-29 | ガルダ，ケキ，ホルムスジ | Ｎ−アルキルカルバゾールとその誘導体を合成する方法 |
| CN115746202B (zh) * | 2022-11-07 | 2023-10-13 | 滁州康华电子材料有限公司 | 一种水处理剂及其制备方法 |
| CN116943662B (zh) * | 2023-06-13 | 2024-02-20 | 北京海望氢能科技有限公司 | 一种非均相催化剂及其制备方法与应用 |
-
1971
- 1971-07-02 DE DE19712132961 patent/DE2132961C3/de not_active Expired
-
1972
- 1972-06-29 GB GB3051672A patent/GB1338885A/en not_active Expired
- 1972-06-29 CH CH978572A patent/CH574927A5/xx not_active IP Right Cessation
- 1972-06-30 IT IT2648372A patent/IT963103B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| CH574927A5 (cg-RX-API-DMAC7.html) | 1976-04-30 |
| DE2132961B2 (de) | 1975-03-06 |
| DE2132961A1 (de) | 1973-01-11 |
| GB1338885A (en) | 1973-11-28 |
| IT963103B (it) | 1974-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2132961C3 (de) | Verfahren zur Herstellung von N-Alkytcarbazolen | |
| EP0026291B1 (de) | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd | |
| DE1129153B (de) | Verfahren zur Herstellung von ª-Cyan-ª-Alkyl-ª-phenylacrylsaeureestern | |
| DE1593865A1 (de) | Verfahren zur Isolierung von 4,4'-Diaminodiphenylmethan aus Polyphenylmethylenpolyamingemischen | |
| DE2258484C3 (de) | Verfahren zum Reinigen von rohem 2-Mercaptobenzothiazol | |
| DE1123662B (de) | Verfahren zur Herstellung von Alkylbenzoldiisocyanaten | |
| DE2316459C2 (de) | Verfahren zur Herstellung von 1- Nitrobenzol-2-carbonsäure-alkylester-5-carbonsäureamiden | |
| DE3104310A1 (de) | Verfahren zur herstellung von 5-chlor-2-nitroanilin | |
| DE2045888B2 (de) | Verfahren zur Herstellung von 7-Hydroxydihydrocitronellal aus Citronellal | |
| DE2814860A1 (de) | Verfahren zur herstellung von aromatischen aminen | |
| DE60025614T2 (de) | Verfahren zur herstellung von n-alkyl-bis(thiazolyl)sulfenimiden | |
| EP0021211B1 (de) | Verfahren zur Herstellung von Dimethylcarbonat | |
| DE1026524B (de) | Verfahren zur Herstellung von Polymerisaten aus Olefinen | |
| DE1668034A1 (de) | Verfahren zur Herstellung von Benzylcyaniden und deren Homologen | |
| DE1124960B (de) | Verfahren zur Herstellung von 3-Acetyl-4-oxycumarin | |
| DE2460821A1 (de) | Verfahren zur herstellung von carbonsaeurefluoriden | |
| DE1954808C3 (cg-RX-API-DMAC7.html) | ||
| DE946986C (de) | Verfahren zur Herstellung von ª‡-Acetotetronsaeuren | |
| DE940528C (de) | Verfahren zur Herstellung von Acrylsaeureamid und ª‡-substituierten Acrylsaeureamiden | |
| DE1251736B (cg-RX-API-DMAC7.html) | ||
| DE1032261B (de) | Verfahren zur Abtrennung sekundaerer Amine aus einer primaeres und sekundaeres Amin enthaltenden Mischung | |
| AT214419B (de) | Verfahren zur Herstellung von farblosen oder fast farblosen höhermolekularen Monocarbonsäureamidhalogenmethylverbindungen | |
| AT156164B (de) | Verfahren zur Herstellung von Halogenalkyl- bzw. Halogenaralkylaminen. | |
| AT233551B (de) | Verfahren zur Herstellung chlorsubstituierter Methylisocyaniddichloride | |
| DE848652C (de) | Verfahren zur Herstellung von 1-dialkylcarbaminyl-substituierten Piperazinen mit substituierter 4-Stellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |