CH230216A - Process for the preparation of a derivative of the anthraquinone series. - Google Patents

Process for the preparation of a derivative of the anthraquinone series.

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Publication number
CH230216A
CH230216A CH230216DA CH230216A CH 230216 A CH230216 A CH 230216A CH 230216D A CH230216D A CH 230216DA CH 230216 A CH230216 A CH 230216A
Authority
CH
Switzerland
Prior art keywords
derivative
preparation
anthraquinone series
mole
carried out
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 CH230216A publication Critical patent/CH230216A/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
    • 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

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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. 227585.    Verfahren zur Herstellung eines Derivates der     Anthraehinonreihe.       Es wurde gefunden, dass ein Derivat der       Anthrachinonreihe    hergestellt werden kann,  wenn man 1     Mol        1-Anilido-4,5,8-triamino-          anthrachinon    mit 1     Mol        Bernsteinsäureanhydrid          acyliert.     



  Das neue Produkt ist ein dunkler Farb  stoff, der sich in Wasser mit blaugrüner Farbe  löst und     Acetatkunstseide    in     kräftigen    blau  grünen Tönen färbt.  



  Die     Acylierung    gemäss vorliegendem Ver  fahren wird vorteilhaft in     indifferenten        Lösungs-          bezw.    Verteilungsmitteln durchgeführt, z. B. in  tertiären Basen     (Pyridin,        Dimethylanilin)    oder  in Benzol oder dessen     Substitutionsprodukten,     z. B. in     Dichlorbenzol,    Nitrobenzol oder in       Solventnaphtha.    Es genügt hierbei schon eine  mässige     Erwärmung,    z. B. auf 30-70o C.  



  Das vorliegende Verfahren erlaubt, in ein  facher Weise nur eine der im Ausgangsstoff  enthaltenen     Aminogruppen    zu     acylieren.    Das  Gelingen der Reaktion erkennt man daran,  dass die Gesamtmenge des     wasserunlöslichen            Ausgangsstoffes    bei Verwendung der theo  retischen Menge     bezw.    eines nur geringen,       etwa        5-10        %        betragenden        Überschusses        an          Acylierungsmittel    in ein Produkt übergeführt  wird,

   das     infolge    der     entstehenden    freien       Carbogylgruppe    mit wässerigen     Alkalien     wasserlösliche     Salze    bildet.    <I>Beispiel:

  </I>  9,1 Teile     1-Azilido-4,5,8-triaminoanthra-          chinon    werden in 50 Teilen     Dimethylanilin     mit 2,7 Teilen     Bernsteinsäureanhydrid    1-2  Stunden auf<B>601</B>     erwärmt.    Man giesst hierauf  die Mischung in 150 Teile 11     o/oige    Salzsäure,  filtriert den Niederschlag ab, wäscht ihn neutral,  vermischt ihn mit der     zur    Überführung in das       Natriumsalz    erforderlichen Menge Natronlauge  und dampft im Vakuum zur     Trockne    ein.



      Additional patent to main patent no. 227585. Process for the production of a derivative of the anthraehinone series. It has been found that a derivative of the anthraquinone series can be prepared if 1 mole of 1-anilido-4,5,8-triaminoanthraquinone is acylated with 1 mole of succinic anhydride.



  The new product is a dark dye that dissolves in water with a blue-green color and dyes acetate artificial silk in strong blue-green tones.



  The acylation according to the present process is advantageously carried out in inert solutions, respectively. Distribution means carried out, e.g. B. in tertiary bases (pyridine, dimethylaniline) or in benzene or its substitution products, e.g. B. in dichlorobenzene, nitrobenzene or in solvent naphtha. Moderate warming is sufficient here, e.g. B. to 30-70o C.



  The present process allows only one of the amino groups contained in the starting material to be acylated in a number of ways. The success of the reaction can be seen from the fact that the total amount of the water-insoluble starting material when using the theoretical amount BEZW. only a small, about 5-10% excess of acylating agent is converted into a product,

   which forms water-soluble salts with aqueous alkalis as a result of the resulting free carbogyl group. <I> example:

  9.1 parts of 1-azilido-4,5,8-triaminoanthraquinone in 50 parts of dimethylaniline with 2.7 parts of succinic anhydride are heated to <B> 601 </B> for 1-2 hours. The mixture is then poured into 150 parts of 11% hydrochloric acid, the precipitate is filtered off, washed neutral, mixed with the amount of sodium hydroxide solution required to convert it into the sodium salt and evaporated to dryness in vacuo.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Derivates der Anthrachinonreihe, dadurch gekennzeichnet, dass man 1 Mol 1-Anilido-4, 5, 8-triaminoanthra- chinon mit 1 Mol Bernsteinsäureanhydrid acyliert. Das neue Produkt ist ein dunkler Farb stoff, der sich in Wasser mit blaugrüner Farbe löst und Acetatkunstseide in kräftigen blau grünen Tönen färbt. UNTERANSPRüCHE: 1. Claim: Process for the preparation of a derivative of the anthraquinone series, characterized in that 1 mole of 1-anilido-4, 5, 8-triaminoanthraquinone is acylated with 1 mole of succinic anhydride. The new product is a dark dye that dissolves in water with a blue-green color and dyes acetate artificial silk in strong blue-green tones. SUBCLAIMS: 1. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Vornahme der Acylie- rung in einem indifferenten Verteilungsmittel. 2. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Vornahme der Acylie- rung in einer tertiären Base. Process according to the patent claim, characterized by the acylation being carried out in an indifferent distribution medium. 2. Process according to claim, characterized by acylation being carried out in a tertiary base.
CH230216D 1941-10-15 1941-10-15 Process for the preparation of a derivative of the anthraquinone series. CH230216A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH230216T 1941-10-15
CH227585T 1943-06-30

Publications (1)

Publication Number Publication Date
CH230216A true CH230216A (en) 1943-12-15

Family

ID=25727126

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230216D CH230216A (en) 1941-10-15 1941-10-15 Process for the preparation of a derivative of the anthraquinone series.

Country Status (1)

Country Link
CH (1) CH230216A (en)

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