CH212331A - 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
- CH212331A CH212331A CH212331DA CH212331A CH 212331 A CH212331 A CH 212331A CH 212331D A CH212331D A CH 212331DA CH 212331 A CH212331 A CH 212331A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- nitrogen
- naphthalene derivative
- containing naphthalene
- parts
- 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 wer den kann, wenn man 1 Mol 2,6-Dihalogen- naphthalin mit 2 Mol 1-Amino-4-benzoyl- aminoanthrachinon umsetzt.
Das neue Produkt ist ein bräunlich schwarzes, kristallines Pulver, das sich in konzentrierter Schwefelsäure mit olivgrüner Farbe löst, nicht verküpt und einen Schmelz punkt über<B>350'</B> besitzt. Das erhaltene Di- (4'-benzoylamino-1'-anthrachinonyl) -2,6 -di- a.minonaphthalin stellt ein wertvolles Zwi schenprodukt für die Herstellung von Küpen- farbstoffen 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> 15 Teile wasserfreies Natriumcarbonat und 15 Teile entwässertes Natriumacetat werden in 500 Teilen Nitrobenzol so lange im Sieden gehalten, bis 50 Teile Nitrobenzol ab destilliert sind.
Nach dem Abkühlen auf 200' werden 14,3 Teile 2,6 - Dibromnaphthalin, 35,2 Teile 1-Amino-4-benzoylaminoanthra- chinon und 1,3 Teile Kupferchlorür zuge setzt und die Reaktionsmischung 24 Stunden bei 195 bis 205 gerührt. Nun wird heiss filtriert, mit Nitrobenzol sowie mit Benzol und Alkohol gewaschen, und das erhaltene Produkt zur weiteren Reinigung mit verdünn ter Salzsäure ausgekocht, abfiltriert, ge waschen 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 by reacting 1 mole of 2,6-dihalonaphthalene with 2 moles of 1-amino-4-benzoylaminoanthraquinone.
The new product is a brownish black, crystalline powder that dissolves in concentrated sulfuric acid with an olive green color, does not condense and has a melting point of over <B> 350 '</B>. The di- (4'-benzoylamino-1'-anthraquinonyl) -2,6-di-a.minonaphthalene obtained is a valuable intermediate product for the production 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, and acid-binding agents. <I> Example: </I> 15 parts of anhydrous sodium carbonate and 15 parts of dehydrated sodium acetate are boiled in 500 parts of nitrobenzene until 50 parts of nitrobenzene have distilled off.
After cooling to 200 ', 14.3 parts of 2,6-dibromonaphthalene, 35.2 parts of 1-amino-4-benzoylaminoanthraquinone and 1.3 parts of copper chloride are added and the reaction mixture is stirred at 195-205 for 24 hours. It is then filtered hot, washed with nitrobenzene and with benzene and alcohol, and the product obtained is boiled for further purification with dilute hydrochloric acid, filtered off, washed and dried.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH212331T | 1937-12-20 | ||
CH206427T | 1937-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH212331A true CH212331A (en) | 1940-11-15 |
Family
ID=25724303
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH212331D CH212331A (en) | 1937-12-20 | 1937-12-20 | Process for the production of a nitrogen-containing naphthalene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH212331A (en) |
-
1937
- 1937-12-20 CH CH212331D patent/CH212331A/en unknown
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