CH211429A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

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Publication number
CH211429A
CH211429A CH211429DA CH211429A CH 211429 A CH211429 A CH 211429A CH 211429D A CH211429D A CH 211429DA CH 211429 A CH211429 A CH 211429A
Authority
CH
Switzerland
Prior art keywords
production
mol
parts
olive
amino
Prior art date
Application number
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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.)
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Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH211429A publication Critical patent/CH211429A/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)

Description

  

  Verfahren zur Herstellung eines     Chrysenderivates.       Es wurde gefunden, dass ein     Chrysen-          derivat    hergestellt werden kann, wenn man  1     Mol        2,8-Dihalogenchrysen,    1     Mol        1-Amino-          4-benzoylaminoanthrachinon    sowie 1     1M1    4  Amino-2-(N)-1-benzanthrachinonakridon auf  einander einwirken lässt.  



  Das so in sehr guter Ausbeute erhält  liche Umsetzungsprodukt bildet ein blaues  Pulver, das sich in konzentrierter Schwefel  .     säure    zuerst mit rotbrauner, dann mit olive  brauner Farbe löst, einen Schmelzpunkt über       46W1    besitzt und Baumwolle aus oliver     Küpe     in grünen Tönen färbt. Es stellt ein wert  volles Zwischenprodukt dar, das insbesondere  zur Herstellung von Farbstoffen verwendet  werden kann.  



  Die Umsetzung der     2,8-Dihalogenchrysene     mit     1-Amino-4-benzoylaminoanthrachinon    so  wie mit 1     142o1        4-Amino-2-(N)-1-benzantbra-          chinonakridon    wird vorteilhaft durch Erhitzen  ihrer Komponenten in     Lösungs-    oder Ver  dünnungsmitteln, wie z.

   B.     Nitrobenzol,    Chlor  naphthalin oder     Amylalkohol    und zweck-    mässig in Gegenwart von Verbindungen, die  die Abspaltung von Halogenwasserstoff er  leichtern, wie Kupfer oder     Kupferverbindun-          gen,    sowie von säurebindenden Mitteln, wie'       Alkalikarbonaten    und/oder entwässertem Na  triumacetat durchgeführt.  



  <I>Beispiel:</I>  9 Teile entwässertes     Natriumacetat    und  9 Teile     kalz.    Soda werden mit 480 Teilen  Nitrobenzol so lange im Sieden gehalten, bis  48 Teile Nitrobenzol     abdestilliert    sind. Nach  dem Abkühlen. auf     160-1650    werden 23,2  Teile     2,8-Dibromchrysen,    erhalten durch     Di-          bromieren    von     Ohrysen    in     Nitrobenzol,    21  Teile     1-Amino-4-benzoylaminoanthrachinon     und 0,75 Teile     Kupferchlorür    zugefügt und  16 Stunden bei<B>160-1650</B> gerührt.

   Nun  wird heiss filtriert, der Rückstand mit     Nitro-          benzol,    Benzol und Alkohol gewaschen und  zur Reinigung mit verdünnter Salzsäure     äus-          gekocht,        abfiltriert,    ausgewaschen und noch  mals mit Alkohol ausgezogen.

        3,25 Teile des nach dein ersten Absatz  erhaltenen     (4'Benzoylaminoanthrachirronyl)-          1',2-amino-8-bi-omchrysens,    1,8 Teile     4-Amirio-          2-(N)-1-berrzarrthrachirrorrakr#idorr,    je 1,5 Teile       kalzinierte    Soda und<B>1,5</B> Teile entwässertes       Natriumacetat,    sowie<B>0,15</B> Teile Kupfer  chlorür werden in 70 Teilen getrocknetem  Nitrobenzol verteilt und 24 Stunden bei einer  Temperatur von     196-206"    gehalten. Das  Reaktionsgemisch wird heiss filtriert, der  Rückstand mit     Nitrobenzol,    Benzol und Al  kohol gewaschen und zur Reinigung mit ver  dünnter Salzsäure ausgekocht.



  Process for the production of a chrysene derivative. It has been found that a chrysene derivative can be prepared if 1 mol of 2,8-dihalochrysenic, 1 mol of 1-amino-4-benzoylaminoanthraquinone and 1 1M1 of 4 amino-2- (N) -1-benzanthraquinone acridone act on one another leaves.



  The reaction product obtained in this way in very good yield forms a blue powder that is concentrated in sulfur. acid dissolves first with red-brown, then with olive-brown color, has a melting point above 46W1 and dyes cotton from olive vat in green tones. 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-4-benzoylaminoanthraquinone as with 1 142o1 4-amino-2- (N) -1-benzantbra- quinonakridon is advantageous by heating their components in solvents or diluents such as z.

   B. nitrobenzene, chlorine naphthalene 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 dehydrated sodium acetate.



  <I> Example: </I> 9 parts dehydrated sodium acetate and 9 parts lime. Soda is kept at the boil with 480 parts of nitrobenzene until 48 parts of nitrobenzene have distilled off. After cooling down. to 160-1650, 23.2 parts of 2,8-dibromochrysene, obtained by dibrominating Ohrysen in nitrobenzene, 21 parts of 1-amino-4-benzoylaminoanthraquinone and 0.75 part of copper chloride are added and 16 hours at <B> 160- Stirred in 1650.

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

        3.25 parts of the (4'Benzoylaminoanthrachirronyl) -1 ', 2-amino-8-bi-omchrysen obtained after the first paragraph, 1.8 parts of 4-Amirio-2- (N) -1-berrzarrthrachirrorrakr # idorr, each 1.5 parts of calcined soda and <B> 1.5 </B> parts of dehydrated sodium acetate, as well as <B> 0.15 </B> parts of chlorine copper are distributed in 70 parts of dried nitrobenzene and kept for 24 hours at a temperature of 196 The reaction mixture is filtered while hot, the residue is washed with nitrobenzene, benzene and alcohol and boiled with dilute hydrochloric acid for purification.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1 Mol 2,8-Dihalogenchryserr, 1 Mol 1-Amirro- 4-benzoylaminoanthrachinon sowie 1 Mol 4 - Amino - 2 - (N) -1- benzanthrachinonakridon aufeinander einwirken lässt. PATENT CLAIM: Process for the production of a chrysene derivative, characterized in that 1 mol of 2,8-dihalochryserr, 1 mol of 1-amirro-4-benzoylaminoanthraquinone and 1 mol of 4-amino-2 - (N) -1-benzanthraquinone acridone act on one another leaves. Das so erhaltene Umsetzungsprodukt bildet ein blaues Pulver, das sich in konzentrierter Schwefelsäure zuerst mit rotbrauner, dann mit olivebrauner Farbe löst, einen Schmelz punkt über 460' besitzt und Baumwolle aus oliver Küpe in grünen Tönen färbt. Es stellt ein wertvolles Zwischenprodukt dar, das insbesondere zur Herstellung von Farbstoffen verwendet werden kann. LTNTERAN <B>SPRUCH:</B> 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. The reaction product thus obtained forms a blue powder which dissolves in concentrated sulfuric acid first with red-brown, then with olive-brown color, has a melting point above 460 'and dyes cotton from an olive vat in green tones. It is a valuable intermediate that can be used in particular for the production of dyes. LTNTERAN <B> PROPOSAL: </B> Process according to patent 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.
CH211429D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH211429A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211429T 1937-06-21
CH204241T 1937-06-21

Publications (1)

Publication Number Publication Date
CH211429A true CH211429A (en) 1940-09-15

Family

ID=25724027

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211429D CH211429A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH211429A (en)

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