CH204241A - Process for the production of a chrysene derivative. - Google Patents

Process for the production of a chrysene derivative.

Info

Publication number
CH204241A
CH204241A CH204241DA CH204241A CH 204241 A CH204241 A CH 204241A CH 204241D A CH204241D A CH 204241DA CH 204241 A CH204241 A CH 204241A
Authority
CH
Switzerland
Prior art keywords
production
mol
chrysene derivative
acid
amino
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 CH204241A publication Critical patent/CH204241A/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
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
    • 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        Ührysenderfvates.       Es wurde gefunden, dass ein     Ohrysenderi-          vat    hergestellt werden kann, wenn man 1     Mol          2,8-Dihalogenohrysen    mit 2     Mol        1-Amino-5-          benzoylaminoanthrachinori    umsetzt.  



  Das so in sehr guter Ausbeute erhältliche  Umsetzungsprodukt bildet braunoliv gefärbte       Nädelchen,    die sich in konzentrierter Schwe  felsäure mit rotbrauner Farbe lösen. Deren       Schmelzpunkt    liegt über 460  . Auf Grund  der Analyse liegt das     Di-(5'-benzoylamirio-1'-          anthrachirionyl)    - 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-Dihalogerichrysene     mit 1-     Amino    - 5 -     berizoylamirioarithraehinon     wird vorteilhaft durch Erhitzen ihrer     Kom-          poneriten    in     Lösungs-    oder Verdünnungsmit  teln, wie z. B.

   Nitrobenzol, Chlornaphthalin  oder     Amylalkohol    und zweckmässig in Gegen  wart von Verbindungen, die die Abspaltung  von     Halogenwasserstoff    erleichtern, wie Kup  fer oder Kupferverbindungen, sowie von säure-    bindenden Mitteln, wie     Alkalikarbonaten    und  oder entwässertem     Natriumacetatdurchgeführt.       <I>Beispiel:</I>    4,5 Teile entwässertes     Natriumacetat    und  4,5 Teile     calcinierte    Soda werden mit 138 Tei  len Nitrobenzol so lange im Sieden gehalten,  bis 18 Teile Nitrobenzol     abdestilliert    sind.

    Nach dem Abkühlen auf     190-2001    (Öltempe  ratur) werden 5,8 Teile     2,8-Dibrornchrysen,     erhalten durch     Dibromieren    von     Chrysen    in  Nitrobenzol, 10,5 Teile     1-Amino-5-berizoyl-          aminoanthrachinon    und 0,4 Teile     gupferchlorür     zugefügt und 16 Stunden bei dieser Tempe  ratur gerührt.

   Nun wird heiss filtriert, der  Rückstand mit Nitrobenzol gewaschen, dann  das     Nitrobenzol    mit Wasserdampf     abdestil-          liert    und der Rückstand zur weiteren Reini  gung mit verdünnter Salzsäure ausgekocht,       abfiltriert,    ausgewaschen und getrocknet.  



  Zu demselben Produkte gelangt man, wenn  das     2,8-Dibromchrysen    durch eine äquivalente  Menge     2,8-Dichlorchrysen    ersetzt wird.



  Process for the production of a Ührysenderfvates. It has been found that an Ohrysene derivative can be produced if 1 mole of 2,8-dihalo-ohrysene is reacted with 2 moles of 1-amino-5-benzoylaminoanthraquinori.



  The reaction product, which can be obtained in this way in very good yield, forms needles which are colored brown-olive and dissolve in concentrated sulfuric acid with a red-brown color. Their melting point is above 460. Based on the analysis, the di- (5'-benzoylamirio-1'-anthrachirionyl) - 2,8 - diaminochrysen is available. It is a valuable intermediate product that can be used in particular in the manufacture of dyes.



  The implementation of the 2,8-dihalogerichrysene with 1-amino - 5 - berizoylamirioarithraehinon 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 dehydrated sodium acetate. <I> Example: </I> 4.5 parts of dehydrated sodium acetate and 4.5 parts of calcined soda are kept at the boil with 138 parts of nitrobenzene until 18 parts of nitrobenzene have distilled off.

    After cooling to 190-2001 (oil temperature), 5.8 parts of 2,8-dibrornchrysene, obtained by dibrominating chrysene in nitrobenzene, 10.5 parts of 1-amino-5-berizoyl-aminoanthraquinone and 0.4 part of gupferchlorur are added and stirred at this temperature for 16 hours.

   It is then filtered while hot, the residue is washed with nitrobenzene, then the nitrobenzene is distilled off with steam and the residue is boiled with dilute hydrochloric acid for further cleaning, filtered off, washed out and dried.



  The same product is obtained if the 2,8-dibromochrysenic is replaced by an equivalent amount of 2,8-dichlorochrysenic.

Claims (1)

hATENTAXSPRUCH: Verfahren zur Herstellung eines Chrysen- derivates, dadurch gekennzeichnet, dass man 1 Mo1 2,8-Dihalogencbrysen mit 2 Mol 1- Amino-5-benzoylarninoanthr,aehirion umsetzt. Das so erhaltene Umsetzungsprodukt bil det braunoliv gefärbte Nädeleben; die sich in konzentrierter Schwefelsäure mit rotbrauner Farbe lösen. Deren Schmelzpunkt liegt über 460 . HATENTAXSPRUCH: A process for the production of a chrysene derivative, characterized in that 1 mol of 2,8-dihalogen biscuits are reacted with 2 mol of 1-amino-5-benzoylarninoanthral aehirion. The reaction product thus obtained forms olive-brown colored needle life; which dissolve in concentrated sulfuric acid with a red-brown color. Their melting point is above 460. Auf Grund der Analyse liegt das Di- (5'- benzoylamino -1'- anthrachi nonyl) - 2,8 - di - aminochrysen vor. Es stellt ein wertvolles Zwischenprodukt dar, das insbesondere zur Herstellung von Farbstoffen verwendet wer den 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. On the basis of the analysis, the di- (5'-benzoylamino -1'-anthrachi nonyl) - 2,8 - di - aminochrysen is present. It is a valuable intermediate product that can be used in particular in the manufacture of dyes. SUBClaim: Method according to claim, characterized; that the reaction is carried out in the presence of compounds that facilitate the splitting off of hydrogen halide and acid-binding agents.
CH204241D 1937-06-21 1937-06-21 Process for the production of a chrysene derivative. CH204241A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH204241A true CH204241A (en) 1939-04-30

Family

ID=4444061

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204241D CH204241A (en) 1937-06-21 1937-06-21 Process for the production of a chrysene derivative.

Country Status (1)

Country Link
CH (1) CH204241A (en)

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