CH211036A - Process for the preparation of a phenanthrene derivative. - Google Patents

Process for the preparation of a phenanthrene derivative.

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Publication number
CH211036A
CH211036A CH211036DA CH211036A CH 211036 A CH211036 A CH 211036A CH 211036D A CH211036D A CH 211036DA CH 211036 A CH211036 A CH 211036A
Authority
CH
Switzerland
Prior art keywords
phenanthrene derivative
parts
preparation
condensing agents
brown
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 CH211036A publication Critical patent/CH211036A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24Dyes 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
    • C09B5/26Carbazoles 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

  

  Zusatzpatent     #zum    Hauptpatent     Nr.    208542.    Verfahren zur Herstellung eines     Phenanthrenderivates.       Es wurde gefunden,     dass    ein     Phenanthren-          derivat    hergestellt werden kann, wenn man       Di   <B>-</B>     (Y-        anthrachinonyl)-   <B>6,10 -</B>     diamiriophenan-          thren    mit kondensierenden Mitteln behandelt.  



  Das neue     Phenanthrenderivat    stellt ein  braunes Pulver dar, das Baumwolle aus  blauroter     Küpe    in     rotstichigbraunen    Tönen  <B>f</B>     ärbt.     



  Für die Behandlung mit kondensierenden  Mitteln kommen insbesondere saure konden  sierende Mittel, z. B.     Aluminiumehlorid,    kon  zentrierte Schwefelsäure und     Ohlorsulfonsäure,     in Betracht. Die Behandlung kann bei tiefer,  mittlerer oder erhöhter Temperatur vorgenom  men werden. Es ist von Vorteil, der     Bebancl-          lung    mit kondensierenden Mitteln eine oxy  dierende Behandlung folgen zu lassen, bei  spielsweise mit     Natriumnitrit,        -perborat    oder       -hypochlorit    in     saurern    Medium.

   Das     erhal-          tene'Produkt    kann weiterhin durch Umfällen,       Umküpen    oder     Umkristallisieren    gereinigt  werden.    Das als Ausgangsmaterial verwendete     Di-          (V-        anthrachinonyl)-6,10   <B>-</B>     diaminophenanthren     kann wie folgt hergestellt werden:

    <B>5</B> Teile<B>6,10</B>     -Dibromphenanthren,        Smp.     145-146<B>0,</B> hergestellt durch     Bromieren    von       10-Bromphenanthren    in     Schwef61kohlenstoff     nach Annalen der Chemie, Band 321, Seite  248, oder durch     Bromieren    von     10-Brom-          phenanthren    in     Tetrachlorkohlenstoff,    4,5 Teile  wasserfreies     Natriumearbonat,    4,5<B>,</B> Teile  entwässertes     Natriumacetat,   <B>6,7</B> Teile     1-          Aminoanthrachinori    und 0,

  4 Teile     Kupfer-          chlorür    werden in 84 Teilen getrocknetem  Nitrobenzol verteilt und<B>16</B> Stunden unter       Rückfluss    trocken gerührt. Das Reaktions  gemisch wird heiss filtriert, der Rückstand  mit Nitrobenzol sowie mit     Befizol    und     Alkoh61     ausgewaschen und zur Reinigung zuerst mit  verdünnter Salzsäure, dann mit Alkohol aus  gekocht.

   Man erhält in guter Ausbeute das       Di   <B>-</B>     (Y-        anthrachinonyl)-   <B>6, 10 -</B>     diaminophenan-          thren    als ein schwarzbraunes, kristallines      Pulver, das konzentrierte Schwefelsäure     olive     färbt, bei<B>375-3800</B> schmilzt und nicht     ver-          küpt.     



  <I>Beispiel:</I>  24 Teile wasserfreies     Aluminiumehlorid     werden mit<B>6</B> Teilen Kochsalz vermischt und  unter Rühren bei 1200 verschmolzen. Nun  gibt man<B>1</B> Teil     Di.-(1'-anthrachinoiiyl)-6,10-          diaminopdttrianth   <B>'</B>     ren   <B>-- '</B> zu und rührt während  2 Stunden bei 120-125     '.    Schliesslich trägt  man die Schmelze in Eis aus, kocht mit ver  dünnter Salzsäure auf und filtriert den er  haltenen Farbstoff ab.



  Additional patent # to main patent no. 208542. Process for the production of a phenanthrene derivative. It has been found that a phenanthrene derivative can be produced if di (y-anthraquinonyl) - 6,10 - diamiriophenanthrene is treated with condensing agents.



  The new phenanthrene derivative is a brown powder that grains cotton from a blue-red vat in reddish brown tones <B> f </B>.



  For treatment with condensing agents, in particular, acidic condensing agents such. B. aluminum chloride, concentrated sulfuric acid and chlorosulfonic acid into consideration. The treatment can be carried out at low, medium or high temperatures. It is advantageous to have the balancing with condensing agents followed by an oxidizing treatment, for example with sodium nitrite, perborate or hypochlorite in an acidic medium.

   The product obtained can also be purified by reprecipitation, recirculation or recrystallization. The di- (V- anthraquinonyl) -6,10 <B> - </B> diaminophenanthrene used as starting material can be produced as follows:

    <B> 5 </B> parts <B> 6,10 </B> -dibromophenanthrene, melting point 145-146 <B> 0, </B> produced by brominating 10-bromophenanthrene in carbon sulfur according to Annalen der Chemie, Volume 321, page 248, or by brominating 10-bromophenanthrene in carbon tetrachloride, 4.5 parts of anhydrous sodium carbonate, 4.5 parts, dehydrated sodium acetate, 6.7 parts Parts 1- Aminoanthraquinori and 0,

  4 parts of copper chloride are distributed in 84 parts of dried nitrobenzene and the mixture is stirred under reflux for <B> 16 </B> hours until dry. The reaction mixture is filtered hot, the residue is washed out with nitrobenzene and with Befizol and alcohol and, for cleaning, first boiled with dilute hydrochloric acid and then with alcohol.

   The di (Y-anthraquinonyl) - 6, 10 - diaminophenanthene is obtained in good yield as a blackish-brown, crystalline powder which gives concentrated sulfuric acid an olive color at < B> 375-3800 </B> melts and does not cap.



  <I> Example: </I> 24 parts of anhydrous aluminum chloride are mixed with <B> 6 </B> parts of table salt and melted while stirring at 1200. Now add <B> 1 </B> part of di .- (1'-anthrachinoiiyl) -6,10-diaminopdttrianth <B> '</B> ren <B> -' </B> and stir during 2 hours at 120-125 '. Finally, the melt is poured out in ice, boiled with dilute hydrochloric acid and the dye obtained is filtered off.

 

Claims (1)

PATENTANSPRUCII: Verfahren zur Herstellung eines Phen- anthrenderivates, dadurch gekennzeichnet, dass man Di-(1'-antbrachinonyl)-6,10-diaminophen- anthren mit kondensierenden Mitteln be handelt. Das neue Phenanthrenderivat stellt ein braunes Pulver dar, das Baumwolle aus blau roter Küpe in rotstichigbraunen Tönen färbt. PATENT CLAIM: Process for the production of a phenanthrene derivative, characterized in that di- (1'-antbrachinonyl) -6,10-diaminophenanthrene is treated with condensing agents. The new phenanthrene derivative is a brown powder that dyes cotton from a blue-red vat in reddish-brown tones.
CH211036D 1938-03-02 1938-03-02 Process for the preparation of a phenanthrene derivative. CH211036A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211036T 1938-03-02
CH208542T 1938-03-02

Publications (1)

Publication Number Publication Date
CH211036A true CH211036A (en) 1940-08-15

Family

ID=25724549

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211036D CH211036A (en) 1938-03-02 1938-03-02 Process for the preparation of a phenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH211036A (en)

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