DE77329C - Process for the preparation of auramine - Google Patents
Process for the preparation of auramineInfo
- Publication number
- DE77329C DE77329C DENDAT77329D DE77329DA DE77329C DE 77329 C DE77329 C DE 77329C DE NDAT77329 D DENDAT77329 D DE NDAT77329D DE 77329D A DE77329D A DE 77329DA DE 77329 C DE77329 C DE 77329C
- Authority
- DE
- Germany
- Prior art keywords
- auramine
- preparation
- amidobenzamide
- dimethylaniline
- dimethyl
- 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
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 44077 sind als Zwischenproducte zur Darstellung von tetraalkylirten Diamidobenzophenonen eine grofse Anzahl von substituirten Auraminen beschrieben, die durch Einwirkung von Phosphoroxychlorid auf die substituirten Dialkylamidobenzamide und .Alkylaniline entstehen. Das nicht substituirte DimethylamidobenzamidIn the patent specification No. 44077 are as intermediate products for the preparation of tetraalkylated Diamidobenzophenones have described a large number of substituted auramines, those by the action of phosphorus oxychloride on the substituted dialkylamidobenzamides and .Alkylanilines are formed. The unsubstituted dimethylamidobenzamide
(CHJ2N-C6H4-CONH2 (CHJ 2 NC 6 H 4 -CONH 2
liefert nach dem Verfahren des Patentes Nr. 44077 kein Auramin. Letzteres bildet sich indessen beim Erhitzen von Dimethyl-p-Amidobenzamid mit Dimethylanilin bei Gegenwart von Chlorzink. does not provide auramine by the method of Patent No. 44077. The latter, however, forms when heating dimethyl-p-amidobenzamide with dimethylaniline in the presence of zinc chloride.
Die Reaction verläuft im Sinne folgender Formelgleichung:The reaction proceeds in the sense of the following equation:
(C HJ, N C6 Ht C O NH2 + C6 H, N(C HJ2 (C HJ, N C 6 H t CO NH 2 + C 6 H, N (C HJ 2 = (C §>Λ — ^- C6 Η*\ c NH + H 0 = (C §> Λ - ^ - C 6 Η * \ c NH + H 0
Das hierbei als Ausgangsmaterial verwendete Dimethyl-p-Amidobenzamid ist bislang nicht bekannt geworden. Es entsteht aus dem entsprechenden Säurechlorid (welches beispielsweise aus Dimethylanilin und Phosgengas oder aus Dimethylamidobenzoesäure und den Chloriden des Phosphors erhalten wird) durch Behandeln mit Ammoniak. Das Dimethyl-p-amidobenzamid krystallisirt in Nädelchen vom Schmelzpunkt 206 ° und ist in heifsem Wasser und in heifsem Alkohol löslich.The dimethyl-p-amidobenzamide used here as the starting material is not yet known. It arises from the corresponding acid chloride (which for example from dimethylaniline and phosgene gas or from dimethylamidobenzoic acid and the chlorides of phosphorus is obtained) by treating with ammonia. The dimethyl-p-amidobenzamide crystallizes in needles with a melting point of 206 ° and is in hot water and in soluble in hot alcohol.
17 kg Dimethyl - ρ - amidobenzamid werden mit 25 kg salzsaurem Dimethylanilin und 30 kg Chlorzink etwa 5 Stunden lang im Oelbad bei Temperaturen von 160 bis 200° erhitzt. Die Schmelze färbt sich im Verlauf des Processes tief gelb. Sobald keine Zunahme der Intensität dieser Färbung mehr zu beobachten ist, wird die Schmelze mit kaltem Wasser zur Entfernung von Chlorzink und salzsaurem Dimethylanilin ausgezogen und der Rückstand in heifsem Wasser gelöst. Aus der filtrirten Lösung scheidet sich das Auramin auf Zusatz von Kochsalz in krystallinischer Form ab.17 kg of dimethyl - ρ - amidobenzamide with 25 kg of hydrochloric acid dimethylaniline and 30 kg of zinc chloride for about 5 hours in an oil bath Temperatures from 160 to 200 ° heated. The melt changes color in the course of the process deep yellow. As soon as there is no longer any increase in the intensity of this coloration the melt with cold water to remove zinc chloride and hydrochloric acid dimethylaniline pulled out and the residue dissolved in hot water. From the filtered solution the auramine separates in crystalline form on the addition of table salt.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE77329C true DE77329C (en) |
Family
ID=350144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT77329D Expired - Lifetime DE77329C (en) | Process for the preparation of auramine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE77329C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429535A (en) * | 1944-03-21 | 1947-10-21 | Winthrop Chem Co Inc | Alkylaminobenzamides |
-
0
- DE DENDAT77329D patent/DE77329C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429535A (en) * | 1944-03-21 | 1947-10-21 | Winthrop Chem Co Inc | Alkylaminobenzamides |
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