CH211430A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH211430A
CH211430A CH211430DA CH211430A CH 211430 A CH211430 A CH 211430A CH 211430D A CH211430D A CH 211430DA CH 211430 A CH211430 A CH 211430A
Authority
CH
Switzerland
Prior art keywords
production
chrysene derivative
mol
acid
aminoanthraquinone
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 CH211430A publication Critical patent/CH211430A/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
    • 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
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/325—Dyes with no other substituents than the amino groups
    • 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

  

  Zusatzpatent zum     Hauptpatent    Nr. 204241.    Verfahren zur Herstellung eines     Chrysenderivates.       Es wurde gefunden, dass ein     Chrysen-          derivat    hergestellt werden kann, wenn man  1     Mol        2,8-Dihalogenchrysen    mit     2Mol    1  Aminoanthrachinon umsetzt.  



  Das so in sehr guter Ausbeute erhältliche  Umsetzungsprodukt bildet braunviolette     Nä-          delchen,    die aus     a-Chlornaphthalin    umkristal  lisiert werden können. Sie lösen sich in kon  zentrierter Schwefelsäure mit brauner Farbe  und besitzen einen Schmelzpunkt über 400".  Auf Grund der Analyse liegt das     Di-(1'-an-          thrachinonyl)    -     2,8-diaminochrysen    vor. Es  stellt ein wertvolles Zwischenprodukt dar,  das insbesondere zur Herstellung von Farb  stoffen verwendet werden kann.  



  Die Umsetzung der     2,8-Dihalogenchrysene     mit     1-Aminoanthrachinon    wird vorteilhaft  durch Erhitzen ihrer Komponenten in Lösungs  oder Verdünnungsmitteln, wie z. B.     Nitro-          benzol,    Chlornaphthalin oder     Amylalkohol     und zweckmässig in Gegenwart von Verbin  dungen, die die Abspaltung von     Halogen-          wasserstoff    erleichtern, wie Kupfer oder    Kupferverbindungen, sowie säurebindenden  Mitteln, wie     Alkalikarbonaten    und/oder ent  wässertem     Natriumacetat    durchgeführt.

      <I>Beispiel:</I>  46,8 Teile     2,8-Dibromchrysen,    erhalten  durch     Dibromieren    von     Chrysen    in Eisessig  nach     Ber.    60, S. 145 oder nach     J.        pr.        Ch.    (2),  9, 275, 56 Teile     1-Aminoanthrachinon,    9,6  Teile     Kupferchlorür    und 54 Teile entwässer  tes     Natriumacetat    werden mit 720 Teilen  Nitrobenzol während 16 Stunden bei einer  Temperatur von     190-2001    verrührt.

   Dabei  scheidet sich das Umsetzungsprodukt ab und  kann durch Filtration, Waschen mit     Nitro-          benzol,    Alkohol und Wasser abgetrennt wer  den.Zur Entfernung der Kupferverbindungen  wird mit verdünnter Salzsäure ausgekocht,  hierauf filtriert, mit Wasser säurefrei gewa  schen und getrocknet.



  Additional patent to main patent no. 204241. Process for the production of a chrysene derivative. It has been found that a chrysene derivative can be produced if 1 mole of 2,8-dihalochrysene is reacted with 2 moles of 1 aminoanthraquinone.



  The reaction product obtainable in this way in very good yield forms brown-violet needles which can be recrystallized from α-chloronaphthalene. They dissolve in concentrated sulfuric acid with a brown color and have a melting point above 400 ". Based on the analysis, the di- (1'-anthrachinonyl) - 2,8-diaminochrysenic is present. It is a valuable intermediate product can be used in particular for the production of dyes.



  The implementation of the 2,8-dihalochrysenes with 1-aminoanthraquinone is advantageous by heating their 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 splitting off of hydrogen halide, such as copper or copper compounds, and acid-binding agents such as alkali carbonates and / or ent watered sodium acetate.

      <I> Example: </I> 46.8 parts of 2,8-dibromochrysenic, obtained by dibrominating chrysene in glacial acetic acid according to Ber. 60, p. 145 or after J. pr. Ch. (2), 9, 275, 56 parts of 1-aminoanthraquinone, 9.6 parts of copper chloride and 54 parts of dehydrated sodium acetate are stirred with 720 parts of nitrobenzene for 16 hours at a temperature of 190-2001.

   The reaction product separates out and can be separated off by filtration, washing with nitrobenzene, alcohol and water. To remove the copper compounds, boil with dilute hydrochloric acid, then filter, wash acid-free with water and dry.

Claims (1)

PATENTANSPRÜCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1 Mol 2,8-Dihalogencbrysen mit 2 Mol 1- Aminoanthrachinon umsetzt. Das so erhaltene Umsetzungsprodukt bil det braunviolette Nädelchen, die aus a-Chlor- naphthalin umkristallisiert werden können. PATENT CLAIM: Process for the production of a chrysene derivative, characterized in that 1 mol of 2,8-dihalogenous bisque is reacted with 2 mol of 1-aminoanthraquinone. The reaction product obtained in this way forms brown-violet needles which can be recrystallized from α-chloronaphthalene. Sie lösen sich in konzentrierter Schwefel säure mit brauner Farbe und besitzen einen Schmelzpunkt über 4001. Auf Grund der Analyse liegt das Di.(1'-aritbrachinonyl)-2,8- diaminochrysen vor. Es stellt ein wertvolles Zwischenprodukt dar, das insbesondere zur Herstellung von Farbstoffen verwendet werden kann. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Gmsetzun g in<I>Gegen-</I> wart von Verbindungen, die die Abspaltung von Halogenwasserstoff erleichtern, sowie von säurebindenden Mitteln durchgeführt wird. They dissolve in concentrated sulfuric acid with a brown color and have a melting point above 4001. Based on the analysis, the di. (1'-aritbrachinonyl) -2,8-diaminochrysen is present. It is a valuable intermediate that can be used in particular for the production of 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 and of acid-binding agents.
CH211430D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211430A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211430T 1937-06-21
CH204241T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211430A true CH211430A (en) 1940-09-15

Family

ID=25724028

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211430D CH211430A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211430A (en)

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