CH211037A - Process for the preparation of a phenanthrene derivative. - Google Patents

Process for the preparation of a phenanthrene derivative.

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Publication number
CH211037A
CH211037A CH211037DA CH211037A CH 211037 A CH211037 A CH 211037A CH 211037D A CH211037D A CH 211037DA CH 211037 A CH211037 A CH 211037A
Authority
CH
Switzerland
Prior art keywords
phenanthrene derivative
preparation
parts
condensing agents
benzacridone
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 CH211037A publication Critical patent/CH211037A/en

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Classifications

    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/26—Carbazoles of the anthracene series

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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     Phenanthrenderivates.       Es wurde gefunden, dass ein     Phenanthren-          derivat    hergestellt werden kann, wenn man  das Umsetzungsprodukt aus 2     Mol        4-Amino-          anthrachinon-2,1(N)-benzacridon    und 1     Mol          6,10-Dihalogenphenanthren    mit kondensieren  den Mitteln behandelt.  



  Das neue     Phenanthrenderivat    stellt ein  schwarzes Pulver dar, das Baumwolle aus       brauner        Iiüpe    in     olivgrauen    Tönen färbt.  



  Für die Behandlung mit kondensierenden  Mitteln kommen insbesondere saure konden  sierende Mittel, zum Beispiel Aluminium  chlorid, konzentrierte Schwefelsäure und       Chlorsulfonsäure    in Betracht. Die Behand  lung kann bei tiefer, mittlerer oder erhöhter  Temperatur vorgenommen werden.

   Es ist von  Vorteil, der Behandlung mit kondensierenden       Mitteln    eine     oxydierende    Behandlung folgen  zu lassen, beispielsweise mit     Natriumnitrit,          -perborat    oder     -hypochlorit    in saurem     M-e-          dium.    Das erhaltene Produkt kann weiterhin  durch Umfällen,     Umküpen    oder     Umkristalli-          sieren        gereinigt    werden.

      Das als Ausgangsmaterial     verwendete     Umsetzungsprodukt kann wie folgt herge  stellt werden:  3,36     Teile        6,10-Dibromplienanthren,    6,8  Teile     4-Aminoanthrachinon-1(N),2-benzacri-          don,    3 Teile     wasserfreies        Natriumcarbonat,     3     Teile        entwässertes        Natriumacetat    und 0,

  3  Teile     gupferchlorür    werden in 70 Teilen     Ni-          trobenzol    verteilt und     unter        Rühren    zum Sie  den erhitzt. Nach beendigter     Reaktion    wird  heiss     filtriert    und der Rückstand durch  Waschen mit Nitrobenzol und     Alkohol    und  Auskochen mit     verdünnter    Salzsäure gerei  nigt.

   Das in ausgezeichneter Ausbeute er  haltene Produkt     stellt        einblaugrünes,    kristal  lines Pulver dar, das sich in     konzentrierter     Schwefelsäure mit schwarzvioletter Farbe  löst und Baumwolle aus rotbrauner     güpe     grün färbt.  



  <I>Beispiel:</I>  1 Teil .des     Umsetzungsproduktes    aus 1  Mal     6,10-Dibromphenanthren    und 2     Mol        4-          Aminoanthrachino,n-1(N),2-benzacridon    wird      bei 120' in eine Schmelze von 24 Teilen Alu  miniumchlorid und 6 Teilen     Natriumchlorid          eingetragen.    Nach zweistündigem Rühren     bei     120-125 " wird die Schmelze in Eis ausge  tragen, mit verdünnter Salzsäure aufgekocht  und der ausgefallene     Farbstoff    filtriert und  gewaschen.



  Process for the preparation of a phenanthrene derivative. It has been found that a phenanthrene derivative can be prepared if the reaction product of 2 moles of 4-aminoanthraquinone-2,1 (N) -benzacridone and 1 mole of 6,10-dihalophenanthrene is treated with condensing agents.



  The new phenanthrene derivative is a black powder that dyes brown cotton in olive-gray tones.



  For the treatment with condensing agents, acidic condensing agents, for example aluminum chloride, concentrated sulfuric acid and chlorosulfonic acid, are particularly suitable. The treatment can be carried out at low, medium or high temperatures.

   It is advantageous to allow treatment with condensing agents to be followed by an oxidizing treatment, for example with sodium nitrite, perborate or hypochlorite in acidic M-edium. The product obtained can furthermore be purified by reprecipitation, recirculation or recrystallization.

      The reaction product used as starting material can be prepared as follows: 3.36 parts 6,10-dibromoplienanthrene, 6.8 parts 4-aminoanthraquinone-1 (N), 2-benzacridone, 3 parts anhydrous sodium carbonate, 3 parts dehydrated sodium acetate and 0,

  3 parts of gupferchlorur are distributed in 70 parts of nitrobenzene and heated to you while stirring. When the reaction has ended, the mixture is filtered hot and the residue is purified by washing with nitrobenzene and alcohol and boiling with dilute hydrochloric acid.

   The product, which is obtained in excellent yield, is a blue-green, crystalline powder that dissolves in concentrated sulfuric acid with a black-violet color and dyes cotton from red-brown güpe green.



  <I> Example: </I> 1 part of the reaction product of 1 time 6,10-dibromophenanthrene and 2 mol of 4-aminoanthraquinone, n-1 (N), 2-benzacridone is converted into a melt of 24 parts of aluminum at 120 ' Minium chloride and 6 parts of sodium chloride entered. After two hours of stirring at 120-125 ", the melt is carried out in ice, boiled with dilute hydrochloric acid and the precipitated dye is filtered and washed.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Phen- anthrenderivates, dadurch gekennzeiebnet, da.B man das Umsetzungsprodukt aus 2 Mol 4 - Aminoanthrachinon - 2,1(N) - benzacridon und 1 Mal 6,10-Dihalogenphenanthren mit kondensierenden Mitteln behandelt. Das neue Phenanthrenderivat stellt ein schwarzes Pulver dar, das Baumwolle aus brauner Küpe in olivgrauen Tönen färbt. PATENT CLAIM: Process for the production of a phenanthrene derivative, characterized by the fact that the reaction product of 2 moles of 4 - aminoanthraquinone - 2,1 (N) - benzacridone and 1 time 6,10-dihalophenanthrene is treated with condensing agents. The new phenanthrene derivative is a black powder that dyes cotton from a brown vat in olive-gray tones.
CH211037D 1938-03-02 1938-03-02 Process for the preparation of a phenanthrene derivative. CH211037A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH208542T 1938-03-02
CH211037T 1938-03-02

Publications (1)

Publication Number Publication Date
CH211037A true CH211037A (en) 1940-08-15

Family

ID=25724550

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211037D CH211037A (en) 1938-03-02 1938-03-02 Process for the preparation of a phenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH211037A (en)

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