CH212334A - Process for the production of a nitrogen-containing naphthalene derivative. - Google Patents
Process for the production of a nitrogen-containing naphthalene derivative.Info
- Publication number
- CH212334A CH212334A CH212334DA CH212334A CH 212334 A CH212334 A CH 212334A CH 212334D A CH212334D A CH 212334DA CH 212334 A CH212334 A CH 212334A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrogen
- mol
- naphthalene derivative
- production
- containing naphthalene
- Prior art date
Links
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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/36—Amino acridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen Naphthalinderivates. Es wurde gefunden, dass ein stickstoff haltiges Naphthalinderivat hergestellt werden kann, wenn man 1 Mol 2,6-Dihalogennaph- thalin gleichzeitig mit 1 Mol 1-Amino-5-ben- zoylaminoanthrachinon und mit 1 Mol 1- Amino-4-benzoylaminoanthrachinon umsetzt.
Das neue Produkt ist ein braunschwarzes, kristallines Pulver, das bei<B>300'</B> noch nicht schmilzt, sich in konzentrierter Schwefelsäure mit grüner Farbe löst und nicht verküpt. Es stellt ein wertvolles Zwischenprodukt für die Herstellung von Küpenfarbstoffen dar.
Als 2,6-Dihalogennaphthalin kann bei spielsweise 2,6-Dibromnaphthalin verwendet werden.
Die Umsetzung wird vorteilhaft durch Erhitzen der Komponenten in Lösungs- oder Verdünnungsmitteln, wie z. B. Amylalkohol, Nitrobenzol oder Naphthalin, und zweck mässig in Anwesenheit von Katalysatoren, wie Kupfer oder Kupferverbindungen, sowie von säurebindenden Mitteln, durchgeführt. <I>Beispiel:
</I> 4,3 Teile 2,6-Dibromnaphthalin werden mit 5,3 Teilen 1 - Amino - 5 - benzoylamino- anthrachinon, 5,3 Teilen 1-Amino-4-benzoyl- aminoanthrachinon, 0,4 Teilen Kupferchlorür, 4,5 Teilen wasserfreiem Natriumcarbonat und 4,5 Teilen entwässertem Natriumacetat in 90 Teilen trockenem Nitrobenzol unter Rühren zum Sieden erhitzt.
Nach beendigter Reak tion wird heiss filtriert, der Rückstand mit Nitrobenzol, Benzol und Alkohol gewaschen, mit verdünnter Salzsäure ausgekocht, fil triert, gewaschen und getrocknet.
Process for the production of a nitrogen-containing naphthalene derivative. It has been found that a nitrogen-containing naphthalene derivative can be produced if 1 mol of 2,6-dihalogenaphthalene is reacted simultaneously with 1 mol of 1-amino-5-benzoylaminoanthraquinone and with 1 mol of 1-amino-4-benzoylaminoanthraquinone.
The new product is a brown-black, crystalline powder that does not melt at <B> 300 '</B>, dissolves in concentrated sulfuric acid with a green color and does not condense. It is a valuable intermediate for the manufacture of vat dyes.
2,6-Dibromonaphthalene, for example, can be used as 2,6-dihalonaphthalene.
The reaction is advantageously carried out by heating the components in solvents or diluents, such as. B. amyl alcohol, nitrobenzene or naphthalene, and conveniently carried out in the presence of catalysts such as copper or copper compounds, as well as acid-binding agents. <I> example:
4.3 parts of 2,6-dibromonaphthalene are mixed with 5.3 parts of 1-amino-5-benzoylamino-anthraquinone, 5.3 parts of 1-amino-4-benzoyl-aminoanthraquinone, 0.4 parts of copper chloride, 4 , 5 parts of anhydrous sodium carbonate and 4.5 parts of dehydrated sodium acetate in 90 parts of dry nitrobenzene heated to the boil with stirring.
After the reaction has ended, the mixture is filtered hot, the residue is washed with nitrobenzene, benzene and alcohol, boiled with dilute hydrochloric acid, filtered, washed and dried.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH212334T | 1937-12-20 | ||
CH206427T | 1937-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH212334A true CH212334A (en) | 1940-11-15 |
Family
ID=25724306
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH212334D CH212334A (en) | 1937-12-20 | 1937-12-20 | Process for the production of a nitrogen-containing naphthalene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH212334A (en) |
-
1937
- 1937-12-20 CH CH212334D patent/CH212334A/en unknown
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