CH137740A - Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone. - Google Patents

Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone.

Info

Publication number
CH137740A
CH137740A CH137740DA CH137740A CH 137740 A CH137740 A CH 137740A CH 137740D A CH137740D A CH 137740DA CH 137740 A CH137740 A CH 137740A
Authority
CH
Switzerland
Prior art keywords
preparation
thiophanthrenequinone
benzo
dioxy
weight
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH137740A publication Critical patent/CH137740A/en

Links

Description

  

  Verfahren zur Darstellung von     1.4-Diogy-benzo-thiophanthrenehinon.       Es wurde gefunden, dass man     hydroxy-          lierte        Thiophantrenchinone    erhält,     wenn    man       Thiophen-2.8-dicarbonsäuren    oder deren An-         hydride    mit     Plrenolen    der     Einwirkung    saurer  Kondensationsmittel bei höherer Temperatur  unterwirft.

   Die Reaktion vollzieht sich zum  Beispiel nach folgender Gleichung:  
EMI0001.0010     
    Überraschend ist, dass man in einem Arbeits  gang ohne wesentliche     Zersetzung    der     lretero-          cyklischen        o-Dicarbonsäuren    direkt zu den       Chinonkörpern    gelangt. Die neuen Verbin  dungen sind wertvoll als Ausgangsmate  rialien für die Herstellung von Farbstoffen.  



  Gegenstand dieses Patentes ist ein Ver  fahren zur Darstellung von     1.4-Dioxybenzo-          thiophanthrerrchinon    der folgenden Formel:  
EMI0001.0018     
    dadurch gekennzeichnet, dass man     Thionapthen-          2.        3-dicarbonsäureanhydrid    mit     Hydrochinon    in  Gegenwart eines sauren Kondensationsmittels  umsetzt.

   Die erhaltene Verbindung soll zur  Herstellung von     Farbstoffen    Verwendung       finden.            Beispiel:       Ein Gemisch von 10 Gewichtsteilen     Thio-          naphten-2.3-dicarbonsäureanhydrid    und 6  Gewichtsteilen     Hydrochinon    wird bei 180  in  eine Schmelze von 10 Gewichtsteilen Koch  salz und 50 Gewichtsteilen Aluminiumchlorid  unter Rühren eingetragen, die Temperatur      auf 190  gesteigert und während 5 Stunden  gehalten. Dann wird mit Eis und Salzsäure  zersetzt und aufgearbeitet.

   Das entstandene  1.     4-Dioxy-benzo-thiopharithrenchinon     
EMI0002.0002     
    kann über die     Diacetylverbindung    oder durch       Umkristallisieren    aus     Pyridin    gereinigt werden.  Es bildet rote Blättchen vom Schmelzpunkt       253-2540.  



  Process for the preparation of 1,4-diogy-benzo-thiophanthrenehinone. It has been found that hydroxylated thiophantrenequinones are obtained if thiophene-2,8-dicarboxylic acids or their anhydrides with plrenols are subjected to the action of acidic condensing agents at a higher temperature.

   The reaction takes place, for example, according to the following equation:
EMI0001.0010
    It is surprising that the quinone bodies can be obtained directly in one operation without substantial decomposition of the heterocyclic o-dicarboxylic acids. The new compounds are valuable as starting materials for the production of dyes.



  The subject of this patent is a process for the preparation of 1,4-Dioxybenzo- thiophanthrerrquinone of the following formula:
EMI0001.0018
    characterized in that thionapthene-2. 3-dicarboxylic anhydride is reacted with hydroquinone in the presence of an acidic condensing agent.

   The compound obtained is said to be used for the production of dyes. Example: A mixture of 10 parts by weight of thionaphthene-2,3-dicarboxylic anhydride and 6 parts by weight of hydroquinone is added at 180 to a melt of 10 parts by weight of common salt and 50 parts by weight of aluminum chloride with stirring, the temperature is increased to 190 and held for 5 hours. Then it is decomposed and worked up with ice and hydrochloric acid.

   The resulting 1,4-dioxy-benzo-thiopharithrenequinone
EMI0002.0002
    can be purified via the diacetyl compound or by recrystallization from pyridine. It forms red leaflets with a melting point of 253-2540.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 1.4-Dioxy- benzo-thiophanthrenchinon der folgenden For mel EMI0002.0009 dadurch gekennzeichnet, dass man Thionaph- ten - 2 . 3 - dicarbonsäureanhydrid mit Hydro- chinon bei Gegenwart eines sauren Konden sationsmittels kondensiert. Die Verbindung bildet rote Blättchen vom Schmelzpunkt 253-254 und soll zur Herstellung von Farb stoffen Verwendung finden. PATENT CLAIM: Process for the preparation of 1,4-dioxybenzo-thiophanthrenequinone of the following formula EMI0002.0009 characterized in that one thionaphthens - 2. 3 - dicarboxylic anhydride condensed with hydroquinone in the presence of an acidic condensation agent. The compound forms red flakes with a melting point of 253-254 and is said to be used for the production of dyes.
CH137740D 1927-09-07 1928-08-16 Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone. CH137740A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE137740X 1927-09-07

Publications (1)

Publication Number Publication Date
CH137740A true CH137740A (en) 1930-01-31

Family

ID=5666972

Family Applications (1)

Application Number Title Priority Date Filing Date
CH137740D CH137740A (en) 1927-09-07 1928-08-16 Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone.

Country Status (1)

Country Link
CH (1) CH137740A (en)

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