CH211425A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH211425A
CH211425A CH211425DA CH211425A CH 211425 A CH211425 A CH 211425A CH 211425D A CH211425D A CH 211425DA CH 211425 A CH211425 A CH 211425A
Authority
CH
Switzerland
Prior art keywords
production
mol
chrysene derivative
amino
acid
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH211425A publication Critical patent/CH211425A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/76—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen 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
    • C09B56/00—Azo dyes containing other chromophoric systems
    • C09B56/12—Anthraquinone-azo dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/48—Chrysenes; Hydrogenated chrysenes

Description

  

  Verfahren zur Herstellung eines     Chrysenderivates.       Es wurde gefunden, dass ein     Chrysen-          derivat    hergestellt werden kann, wenn man  1     Mol        2,8-Dihalogenchrysen    mit 2     llol        1-          Amino    - 5 -     acetylaminoanthrachinon    umsetzt.  



  Das so in sehr guter Ausbeute erhältliche  Umsetzungsprodukt bildet     braunolive        Nädel-          chen,    die sich in konzentrierter Schwefelsäure  mit roter Farbe lösen und einen über 4601  liegenden Schmelzpunkt besitzen. Es stellt  ein     wertvolles    Zwischenprodukt dar, das ins  besondere zur Herstellung von Farbstoffen  verwendet werden kann.  



  Die Umsetzung der     2,8-Dihalogenchrysene     mit     1-Amino-5-acetylaminoantbrachinon    wird  vorteilhaft durch Erhitzen ihrer Komponen  ten in     Lösungs-    oder Verdünnungsmitteln,  wie z. B. Nitrobenzol, Chlornaphthalin oder       Amylalkohol    und zweckmässig in Gegenwart  von Verbindungen, die die Abspaltung von       Halogenwasserstoff    erleichtern, wie Kupfer  oder Kupferverbindungen, sowie von säure  bindenden Mitteln, wie     Alkalikarbonaten          und/oder    entwässertem     Natriumacetat    durch  geführt.

      <I>Beispiel:</I>  3 Teile entwässertes     Natriumacetat    und  3 Teile     kalz.    Soda werden mit 96 Teilen  Nitrobenzol so lange im Sieden gehalten, bis  12 Teile Nitrobenzol     abdestilliert    sind. Nach  dem Abkühlen auf 193 bis 203 0     (Ölbadtem-          peratur)    werden 3,9 Teile     2,8-Dibromchrysen,     5,8 Teile     1-Amino-5-acetylaminoanthrachinon     und 0,26 Teile     Kupferchlorür    zugefügt und  18 Stunden bei dieser Temperatur gerührt.

    Nun wird heiss filtriert, der Rückstand mit  Nitrobenzol, Benzol und Alkohol gewaschen  und zur Reinigung mit verdünnter Salzsäure  ausgekocht, filtriert, der Rückstand aus  gewaschen und getrocknet.



  Process for the production of a chrysene derivative. It has been found that a chrysene derivative can be produced if 1 mol of 2,8-dihalochrysenic is reacted with 2 mol 1-amino-5-acetylaminoanthraquinone.



  The reaction product, obtainable in this way in very good yield, forms brown-olive needles which dissolve in concentrated sulfuric acid with a red color and have a melting point above 4601. It is a valuable intermediate product that can be used in particular in the manufacture of dyes.



  The implementation of the 2,8-dihalochrysenes with 1-amino-5-acetylaminoantbrachinon is advantageous th by heating their components in solvents or diluents, such as. B. nitrobenzene, chloronaphthalene or amyl alcohol and conveniently performed in the presence of compounds that facilitate the elimination of hydrogen halide, such as copper or copper compounds, and acid-binding agents such as alkali carbonates and / or dehydrated sodium acetate.

      <I> Example: </I> 3 parts dehydrated sodium acetate and 3 parts lime. Soda is kept at the boil with 96 parts of nitrobenzene until 12 parts of nitrobenzene have distilled off. After cooling to 193-203 0 (oil bath temperature) 3.9 parts of 2,8-dibromochrysenic, 5.8 parts of 1-amino-5-acetylaminoanthraquinone and 0.26 part of copper chloride are added and the mixture is stirred at this temperature for 18 hours.

    It is then filtered hot, the residue is washed with nitrobenzene, benzene and alcohol and, for cleaning, boiled with dilute hydrochloric acid, filtered, the residue is washed out and dried.

Claims (1)

PATENTAI@ISPRUCH Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1 Mol 2,8-Dihalogenchrysen mit 2 Mo1 1- Amino-5-acetylaminoanthrachinon umsetzt. Das so erhaltene Umsetzungsprodukt bil det braunolive Nädelchen, die sich in kon zentrierter Schwefelsäure mit roter Farbe lösen und einen über 460 liegenden Schmelz punkt besitzen. Es stellt ein wertvolles Zwi schenprodukt dar, das insbesondere zur Her stellung von Farbstoffen verwendet werden kann. PATENTAI @ ISPRUCH Process for the production of a chrysene derivative, characterized in that 1 mol of 2,8-dihalochrysene is reacted with 2 mol of 1-amino-5-acetylaminoanthraquinone. The reaction product thus obtained forms brown olive needles which dissolve in concentrated sulfuric acid with a red color and have a melting point above 460. It is a valuable intermediate product that can be used in particular for the manufacture of dyes. UNTERAISPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Umsetzung in Ge- genwart von Verbindungen, die die Abspal tung von Halogenwasserstoff erleichtern, so wie von säurebindenden Mitteln durchgeführt wird. SUBJECT CLAIM: Process according to patent claim, characterized in that the reaction is carried out in the presence of compounds which facilitate the splitting off of hydrogen halide, as well as acid-binding agents.
CH211425D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211425A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204241T 1937-06-21
CH211425T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211425A true CH211425A (en) 1940-09-15

Family

ID=25724024

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211425D CH211425A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211425A (en)

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