DE165226C - - Google Patents
Info
- Publication number
- DE165226C DE165226C DENDAT165226D DE165226DA DE165226C DE 165226 C DE165226 C DE 165226C DE NDAT165226 D DENDAT165226 D DE NDAT165226D DE 165226D A DE165226D A DE 165226DA DE 165226 C DE165226 C DE 165226C
- Authority
- DE
- Germany
- Prior art keywords
- naphthylamine
- dinaphtazine
- ber
- alkalis
- preparation
- 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.)
- Active
Links
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 241000490025 Schefflera digitata Species 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- 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
- C09B17/00—Azine dyes
- C09B17/04—Azine dyes of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Nach A. Wohl und W. Aue (Ber. 34, 2443) entsteht beim Erhitzen von ß-Naphtylamin mit Nitrobenzol und Alkali keine Spur Naphtazin, sondern nur α · ß-Naphtophenazin. Auffallenderweise wird dagegen asymmetrisches α · ß-Dinaphtazin in glatter Reaktion gebildet, wenn man schmelzende Alkalien mit oder ohne Beihilfe von Oxydationsmitteln auf ß-Naphtylamin einwirken läßt. Das Verfahren ist einfacher und billiger als das im Patent 78748 beschriebene, das darin besteht, ß-Naphtylamin in wässeriger Suspension mit einer Chlorkalklösung zu behandeln. Zudem liefert es ein reineres Produkt, da bei Anwendung von Chlorkalk die Bildung von chlorhaltigen Derivaten kaum zu vermeiden ist (vergl. W. M eigen und W. Normann, Ber. 33, 2711).According to A. Wohl and W. Aue (Ber. 34, 2443), β-naphthylamine is formed when heated with nitrobenzene and alkali no trace of naphtazine, only α · ß-naphtophenazine. Strikingly, on the other hand, asymmetric α · ß-dinaphtazine reacts smoothly formed when melting alkalis with or without the aid of oxidizing agents lets act on ß-naphthylamine. The process is simpler and cheaper than the im Patent 78748, which consists of β-naphthylamine in aqueous suspension to be treated with a chlorinated lime solution. In addition, it provides a purer product, since it is formed when chlorinated lime is used of chlorine-containing derivatives can hardly be avoided (cf. W. M Eigen and W. Normann, Ber. 33, 2711).
In 500 kg geschmolzenes Ätzkali werdenBe in 500 kg of molten caustic potash
IOO kg ß-Naphtylamin eingetragen und dieIOO kg of ß-naphthylamine entered and the
- Schmelze 1 bis 2 Stunden auf 190 bis 200° erhitzt. Nach beendeter Operation wird aus- Melt for 1 to 2 hours at 190 to 200 ° heated. When the operation is finished, turns off
der abgekühlten Schmelze das Ätzkali durch Wasser ausgelaugt und der Rückstand zunächst mit verdünnter Salzsäure und dann mit Alkohol ausgekocht. Das asymmetrische α · ß-Dinaphtazin bleibt in gelben Nadeln vom Fp. 2790 zurück. Es ist deshalb besonders wertvoll, weil es beim Nitrieren und nachfolgenden Reduzieren Aminoverbindungen liefert, deren Diazoderivate zur Darstellung von Azofarbstoffen geeignet sind. Schon die Kombination mit R-SaIz hat die Eigenschaft, ungeheizte Baumwolle leicht zu färben. Andererseits läßt sich das Dinaphtazin durch Sulfurieren und Abschmelzen mit Alkalien in ein gut charakterisiertes Oxynaphtazin überführen, das ebenfalls als Ausgangsmaterial zur Darstellung von Farbstoffen großen technischen Wert besitzt.The caustic potash is leached out of the cooled melt by water and the residue is first boiled with dilute hydrochloric acid and then with alcohol. The asymmetrical α · ß-Dinaphtazin remains in yellow needles, mp. 279 0. It is particularly valuable because, on nitration and subsequent reduction, it yields amino compounds whose diazo derivatives are suitable for the preparation of azo dyes. The combination with R-SaIz already has the property of easily dyeing unheated cotton. On the other hand, the dinaphtazine can be converted into a well-characterized oxynaphtazine by sulfurizing and melting with alkalis, which is also of great technical value as a starting material for the preparation of dyes.
Dasselbe asymmetrische α · ß-Dinaphtazin entsteht auch bei der Kalischmelze des bekannten β · ß-Azonaphthalins (vergl. Meisenheimer und Witte, Ber. 36, 4154).The same asymmetrical α · ß-dinaphtazine is also produced when the known potash is melted β · β-azonaphthalene (see Meisenheimer and Witte, Ber. 36, 4154).
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE165226C true DE165226C (en) |
Family
ID=430751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT165226D Active DE165226C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE165226C (en) |
-
0
- DE DENDAT165226D patent/DE165226C/de active Active
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