AT69808B - Process for the preparation of carbazole monosulfonic acids. - Google Patents
Process for the preparation of carbazole monosulfonic acids.Info
- Publication number
- AT69808B AT69808B AT69808DA AT69808B AT 69808 B AT69808 B AT 69808B AT 69808D A AT69808D A AT 69808DA AT 69808 B AT69808 B AT 69808B
- Authority
- AT
- Austria
- Prior art keywords
- carbazole
- preparation
- monosulfonic acids
- acids
- monosulfonic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- WTZQJWITZKKMAB-UHFFFAOYSA-N 9h-carbazole-1-sulfonic acid Chemical class C12=CC=CC=C2NC2=C1C=CC=C2S(=O)(=O)O WTZQJWITZKKMAB-UHFFFAOYSA-N 0.000 title claims 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- SDFLTYHTFPTIGX-UHFFFAOYSA-N 9-methylcarbazole Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C2=C1 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von Karbazolmonosulfoaäuren.
Von den Su1fosäuren des Karbazols und seiner Derivate sind bisher nur Polysulfosäuren bekannt. Eine Monosulfosäure herzustellen, ist bisher nicht gelungen. Nach den Angaben der Literatur (vgl. Schwalbe und Wolff, Ber., 44, S. 234 und 236 ; Schultz & Hauenstein, J. pr. [2], 76 [1907], S. 336) lässt sich Karbazol durch Behandeln mit Schwefelsäure nach den üblichen Methoden zwar sulfieren, doch werden hiebei nur Polysulfosäuren erhalten.
Es hat sich nun gezeigt, dass man Monosulfosäuren herstellen kann, wenn man Karbazol bzw. seine N-substituierten Derivate in indifferenten Lösungsmitteln, wie z. B. Nitrobenzol, löst oder fein verteilt und darauf Schwefelsäure oder Chlorsulfonsäure allmählich einwirken lässt.
Die Monosulfosäuren des Karbazols und seiner Derivate bilden wertvolle Ausgangsmaterialien für die Herstellung von Farbstoffen.
Beispiel : 18-1 kg N-Methylkarbazol werden in 180 kg Nitrobenzol gelöst und unter Kühlung langsam mit 11#7 kg Chlorsulfonsäure versetzt. Das Gemisch wird bei etwas höherer Temperatur noch einige Stunden nachgerührt, darauf wird das Nitrobenzol mit Wasser aus-
EMI1.1
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of carbazole monosulfoacids.
Of the sulfonic acids of carbazole and its derivatives, only polysulfonic acids are known to date. It has not yet been possible to produce a monosulfonic acid. According to the information in the literature (cf. Schwalbe and Wolff, Ber., 44, pp. 234 and 236; Schultz & Hauenstein, J. pr. [2], 76 [1907], p. 336), carbazole can be treated with Sulfuric acid is sulfated by the usual methods, but only polysulfonic acids are obtained.
It has now been shown that you can produce monosulfonic acids if you carbazole or its N-substituted derivatives in inert solvents, such as. B. nitrobenzene, dissolves or finely divided and then gradually allows sulfuric acid or chlorosulfonic acid to act.
The monosulfonic acids of carbazole and its derivatives are valuable starting materials for the production of dyes.
Example: 18-1 kg of N-methylcarbazole are dissolved in 180 kg of nitrobenzene and 11 ~ 7 kg of chlorosulfonic acid are slowly added while cooling. The mixture is stirred for a few hours at a slightly higher temperature, then the nitrobenzene is extracted with water.
EMI1.1
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69808X | 1912-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT69808B true AT69808B (en) | 1915-09-10 |
Family
ID=5635179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT69808D AT69808B (en) | 1912-04-27 | 1913-04-25 | Process for the preparation of carbazole monosulfonic acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT69808B (en) |
-
1913
- 1913-04-25 AT AT69808D patent/AT69808B/en active
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