CH211431A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH211431A
CH211431A CH211431DA CH211431A CH 211431 A CH211431 A CH 211431A CH 211431D A CH211431D A CH 211431DA CH 211431 A CH211431 A CH 211431A
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 CH211431A publication Critical patent/CH211431A/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

Description

  

  Zusatzpatent zum     Haupeatent        Nr.    204241.    Verfahren zur Herstellung eines     Chrysenderivates.       Es wurde gefunden,     dass    ein     Chrysen-          derivat    hergestellt werden kann, wenn man  <B>1</B>     Mol        2-Ilalogenehrysen    mit<B>1</B>     Mol        1-Amino-          anthrachinon    umsetzt.  



  Das so in     sehrguterAusbeuteerhältliche     Umsetzungsprodukt bildet rote Nadeln, die  die aus Nitrobenzol umkristallisiert werden  können. Sie weisen einen Schmelzpunkt von  <B>280-285 0</B> auf und lösen sich in konzentrier  ter Schwefelsäure mit brauner Farbe. Auf  Grund der Analyse liegt das     l'-(Anthrachi-          nonyl)-2-aminocliryseii    vor. Es stellt ein  wertvolles Zwischenprodukt dar, das insbe  sondere zur Herstellung von Farbstoffen ver  wendet werden kann.  



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

      <I>Beispiel:</I>  <B>10,3</B> Teile     2-Bromehrysen,    hergestellt durch       Monobromieren    von     Ohrysen    in Nitrobenzol,  <B>6</B> Teile entwässertes     Natriumacetat,   <B>7,5</B> Teile       1-Aminoanthrachinon    und<B>1,6</B> Teile     Kupfer-          ohlorär    werden in 145 Teilen Nitrobenzol  verteilt und während 20 Stunden bei einer  Temperatur von<B>190-2000</B> gehalten.

   Das       Reaktionsgeinisch    wird nach dem Erkalten  filtriert, der Rückstand mit Nitrobenzol sowie  Benzol gewaschen und zur Reinigung mit       etwa   <B>1</B>     %iger        Salzsäure        ausgekocht.        Hierauf     wird filtriert, mit Wasser säurefrei gewaschen  und getrocknet.



  Additional patent to the main patent No. 204241. Process for the production of a chrysene derivative. It has been found that a chrysene derivative can be produced if <B> 1 </B> mole of 2-ilalogenehrysen is reacted with <B> 1 </B> mole of 1-aminoanthraquinone.



  The reaction product, which can be obtained in this way in very good yield, forms red needles which can be recrystallized from nitrobenzene. They have a melting point of <B> 280-285 </B> and dissolve in concentrated sulfuric acid with a brown color. On the basis of the analysis, the l '- (anthraquinoneyl) -2-aminocliryseii is available. It is a valuable intermediate that can be used in particular in the manufacture of dyes.



  The implementation of the 2-Halocbrysene with 1-Aminoanthraquinone is advantageous by heating their components in solvents or diluents, such as. B. nitrobenzene, Ohlorriaphthalin or amyl alcohol and expediently in the presence of connec tions that facilitate the elimination of hydrogen halide, such as copper or copper compounds, and acid-binding agents such as alkali metal carbonates and / or dehydrated sodium acetate.

      <I> Example: </I> <B> 10.3 </B> parts of 2-Bromehrysen, produced by monobromination of Ohrysen in nitrobenzene, <B> 6 </B> parts of dehydrated sodium acetate, <B> 7.5 Parts of 1-aminoanthraquinone and 1.6 parts of copper chloride are distributed in 145 parts of nitrobenzene and kept at a temperature of 190-2000 for 20 hours.

   After cooling, the reaction mixture is filtered, the residue is washed with nitrobenzene and benzene and boiled with about 1% hydrochloric acid for cleaning. It is then filtered, washed acid-free with water and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man <B>1</B> Mol 2-Halogenehrysen mit<B>1</B> Mol 1-Amino- anthrachinon umsetzt. 1)as so erhaltene tImsetzungsprodukt bil det rote Nadeln, die aus Nitroberizol um kristallisiert werden können. PATENT CLAIM: Process for the production of a chrysene derivative, characterized in that <B> 1 </B> mol of 2-halo-erysene is reacted with <B> 1 </B> mol of 1-aminoanthraquinone. 1) The decomposition product obtained in this way forms red needles which can be recrystallized from nitroberizole. Sie weisen einen Schmelzpunkt von 280-285' auf und Iösen sich in konzentrierter Schwefelsäure mit brauner Farbe. Auf Grund der Analyse liegt das l"-(Anthrachinonyl)-2-aminochryseii vor. Es stellt ein wertvolles Zwischenprodukt dar, das insbesondere zur Herstellung von Farb stoffen verwendet werden kann. ÜNTERANSPUtCÜ: 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. They have a melting point of 280-285 'and dissolve in concentrated sulfuric acid with a brown color. Based on the analysis, the l "- (Anthraquinonyl) -2-aminochryseii is available. It is a valuable intermediate product that can be used in particular for the production of dyes. ÜNTERANSPUtCÜ: Process according to patent claim, characterized in that the conversion into Ge presence of compounds that facilitate the elimination of hydrogen halide, such as acid-binding agents.
CH211431D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211431A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204241T 1937-06-21
CH211431T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211431A true CH211431A (en) 1940-09-15

Family

ID=25724029

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211431D CH211431A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211431A (en)

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