CH211426A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH211426A
CH211426A CH211426DA CH211426A CH 211426 A CH211426 A CH 211426A CH 211426D A CH211426D A CH 211426DA CH 211426 A CH211426 A CH 211426A
Authority
CH
Switzerland
Prior art keywords
production
chrysene derivative
mol
parts
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 CH211426A publication Critical patent/CH211426A/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

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

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     Mol    1  Amirro-5-cinnamoylaminoanthrachinon um  setzt.  



  Das so in guter Ausbeute erhältliche Um  setzungsprodukt bildet ein braunes Pulver,  das sich in konzentrierter Schwefelsäure mit  brauner Farbe löst. Es stellt ein wertvolles  Zwischenprodukt dar, das insbesondere zur  Herstellung von Farbstoffen verwendet wer  den kann.  



  Die Umsetzung der     2,8-Dihalogenchrysene     mit     1-Amino-5-cinnamoylaminoanthrachinon     wird vorteilhaft durch Erhitzen ihrer Kom  ponenten in     Lösungs-    oder Verdünnungs  mitteln, wie z. B. Nitrobenzol, Chlornaphthalin  oder     Amylalkohol    und zweckmässig in Ge  genwart von Verbindungen, die die Abspal  tung von     Halogenwasserstoff    erleichtern, wie  Kupfer oder Kupferverbindungen, sowie von  säurebindenden Mitteln, wie     Alkalikarbonaten       und/oder entwässertem     Natriumacetat    durch  geführt.  



  <I>Beispiel:</I>  3 Teile     calzinierte    Soda und 3 Teile ent  wässertes     Natriumacetat    werden mit 108 Tei  len Nitrobenzol so lange im Sieden gehalten,  bis 12 Teile Nitrobenzol     abdestilliert    sind.  Nach dem Abkühlen auf 193 bis 203   wer  den 3,86 Teile     2,8-Dibromchrysen,    7,6 Teile     1-          Amino-5-cirrnamoylaminoanthrachinon    sowie  0,3 Teile     Kupferchlorür    zugefügt und 24 Stun  den bei dieser Temperatur gerührt.

   Nun wird  heiss     abgenutscht,        derRückstandausgewaschen     und zur Reinigung mit verdünnter Salzsäure  ausgekocht,     abfiltriert,    gewaschen und noch  mals mit Alkohol ausgekocht.



      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 of 1 amirro-5-cinnamoylaminoanthraquinone.



  The reaction product obtainable in this way in good yield forms a brown powder which dissolves in concentrated sulfuric acid with a brown color. It is a valuable intermediate product that can be used in particular in the manufacture of dyes.



  The implementation of the 2,8-dihalochrysene with 1-amino-5-cinnamoylaminoanthraquinone is advantageous by heating their components in solvents or diluents, such as. B. nitrobenzene, chloronaphthalene or amyl alcohol and expedient in Ge 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 of calcined soda and 3 parts of dehydrated sodium acetate are kept at the boil with 108 parts of nitrobenzene until 12 parts of nitrobenzene have distilled off. After cooling to 193-203 who added 3.86 parts of 2,8-dibromochrysenic, 7.6 parts of 1-amino-5-cirrnamoylaminoanthraquinone and 0.3 part of copper chloride and stirred for 24 hours at this temperature.

   Now it is sucked off while hot, the residue is washed out and, for cleaning, boiled with dilute hydrochloric acid, filtered off, washed and boiled again with alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1 Mol 2,8-Dihalogenchrysen mit 2 Mol 1- Amino - 5 - ciniramoylaminoarrthr-acirinon um setzt. Das so erhaltene Umsetzungsprodukt bil det ein braunes Pulver, das sich in konzen trierter Schwefelsäure mit brauner Farbe löst. Es stellt ein wertvolles Zwischenpro dukt dar, das insbesondere zur Herstellung von Farbstoffen verwendet werden kann. PATENT CLAIM: Process for the production of a chrysene derivative, characterized in that 1 mol of 2,8-dihalochrysene is converted with 2 mol of 1-amino-5-ciniramoylaminoarrthr-acirinone. The resulting reaction product forms a brown powder which dissolves in concentrated sulfuric acid with a brown color. It is a valuable intermediate product that can be used in particular for the production of dyes. UNTERANSPRUCH: 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. SUBCLAIM: Process according to claim, characterized in that the reaction is carried out in the presence of compounds which facilitate the elimination of hydrogen halide, as well as acid-binding agents.
CH211426D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211426A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211426T 1937-06-21
CH204241T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211426A true CH211426A (en) 1940-09-15

Family

ID=25724025

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211426D CH211426A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211426A (en)

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