CH211423A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH211423A
CH211423A CH211423DA CH211423A CH 211423 A CH211423 A CH 211423A CH 211423D A CH211423D A CH 211423DA CH 211423 A CH211423 A CH 211423A
Authority
CH
Switzerland
Prior art keywords
mol
reaction product
chrysene derivative
production
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 CH211423A publication Critical patent/CH211423A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Chrysenderivates.       Es wurde gefunden, dass ein     Chrysende-          rivat    hergestellt werden kann, wenn man  1     1Mo1        2,8-Dihalogenchrysen    mit 1     Mol        1-          Amino-4-berizoylaminoairthrachinon    umsetzt.  



  Das so in sehr guter Ausbeute erhältliche  Umsetzungsprodukt bildet nach dem     Umkri-          stallisieren    aus     a-Chlornaphthalin    kleine,  blaue     Nädelchen    vom Zersetzungspunkt 380 ,  die sich in konzentrierter Schwefelsäure mit  grüngelber Farbe lösen. Die Lösungsfarbe  schlägt bald nach     braunolive    um. Das neue  Umsetzungsprodukt stellt ein wertvolles Zwi  schenprodukt dar, das insbesondere zur Her  stellung von     Farbstoffen    verwendet werden  kann.  



  Die     Unisetzung    der     2,8-Dihalogenuhi,ysene     mit     1-Amino-4-beiizoylaminoanthrachinon    wird  vorteilhaft durch Erhitzen ihrer Komponenten  in     Lösungs-    oder Verdünnungsmitteln, wie  z. B. Nitrobenzol, Chlornaphthalin oder     Amyl-          alkohol    und zweckmässig in Gegenwart von  Verbindungen, die     die.Abspaltung    von Ha  logenwasserstoff erleichtern, wie Kupfer oder    Kupferverbindungen, sowie von - säurebinden  den Mitteln, wie     Alkalikarbonaten        und/oder     entwässertem     Natriumacetat    durchgeführt.  



       Beispiel:     9 Teile entwässertes     Natriumacetat    und  9 Teile kalt. Soda werden mit 480 Teilen  Nitrobenzol so lange im Sieden gehalten, bis  48 Teile Nitrobenzol     abdestilliert    sind. Nach  dem Abkühlen auf     160-1950    werden 23,2  Teile     2,8-Dibromchrysen,    erhalten durch     Di-          bromieren    von     Chrysen    in Nitrobenzol, 21  Teile     1-Amino-4-benzoylaminoantbrachinon     und 0,75 Teile     Kupferchlorür    zugefügt und  16 Stunden bei 160-165   gerührt.

   Nun wird  heiss filtriert, der Rückstand mit Nitrobenzol,  Benzol und Alkohol gewaschen und zur Rei  nigung mit verdünnter Salzsäure ausgekocht,       abfiltriert,    ausgewaschen und nochmals mit  Alkohol ausgezogen.



  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 1 mol of 1-amino-4-berizoylaminoairthraquinone.



  The reaction product, which can be obtained in this way in very good yield, forms, after recrystallization from α-chloronaphthalene, small, blue needles with a decomposition point of 380, which dissolve in concentrated sulfuric acid with a green-yellow color. The solution color soon changes to brown olive. The new reaction product is a valuable inter mediate product that can be used in particular for the manufacture of dyes.



  The conversion of the 2,8-Dihalogenuhi, ysene with 1-amino-4-beiizoylaminoanthraquinone is advantageous by heating its components in solvents or diluents, such as. B. nitrobenzene, chloronaphthalene or amyl alcohol and expediently carried out in the presence of compounds that facilitate the separation of hydrogen halide, such as copper or copper compounds, and of - acid-binding agents such as alkali carbonates and / or dehydrated sodium acetate.



       Example: 9 parts dehydrated sodium acetate and 9 parts cold. Soda is kept at the boil with 480 parts of nitrobenzene until 48 parts of nitrobenzene have distilled off. After cooling to 160-1950, 23.2 parts of 2,8-dibromochrysene, obtained by dibrominating chrysene in nitrobenzene, 21 parts of 1-amino-4-benzoylaminoantbrachinone and 0.75 part of copper chloride are added and the mixture is heated at 160 ° for 16 hours. 165 stirred.

   The mixture is then filtered hot, the residue is washed with nitrobenzene, benzene and alcohol and boiled with dilute hydrochloric acid for cleaning, filtered off, washed and extracted again with alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1. Mol 9.,8-Dihalogenclir-psen mit 1 Mol 1- Amino-4-benzoylaminoanthraehirion umsetzt. Das so erhaltene Umsetzungsprodukt bil det nach dem Umkristallisieren aus a-Clilor- naplithaliri kleine blaue Nädelchen vom Zer setzungspunkt<B>380,</B> die sich in konzentrierter Schwefelsäure mit grüngelber Farbe lösen. PATENT CLAIM: Process for the preparation of a chrysene derivative, characterized in that 1 mol of 9th, 8-dihalogen chloride is reacted with 1 mol of 1-amino-4-benzoylaminoanthraehirion. After recrystallization from α-clilornaplithaliri, the reaction product obtained in this way forms small blue needles with a decomposition point of <B> 380, </B> which dissolve in concentrated sulfuric acid with a green-yellow color. Die Lösungsfarbe schlägt bald nach Braun olive um. Das neue Umsetzungsprodukt stellt ein wertvolles Zwischenprodukt dar, das ins- besondere zur Herstellung von Farbstoffen verwendet werden kann. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Umsetzung in Gegen wart von Verbindungen, die die Abspaltung von Halogenwasserstoff' erleichtern, sowie von säurebindenden Mitteln durchgeführt wird. The solution color soon changes to brown olive. The new reaction product is a valuable intermediate product that can be used in particular to produce dyes. SUBSTANTIAL 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.
CH211423D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211423A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204241T 1937-06-21
CH211423T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211423A true CH211423A (en) 1940-09-15

Family

ID=25724022

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211423D CH211423A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211423A (en)

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