CH114496A - Process for the preparation of Bz-2'-oxybenzanthrone. - Google Patents

Process for the preparation of Bz-2'-oxybenzanthrone.

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Publication number
CH114496A
CH114496A CH114496DA CH114496A CH 114496 A CH114496 A CH 114496A CH 114496D A CH114496D A CH 114496DA CH 114496 A CH114496 A CH 114496A
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CH
Switzerland
Prior art keywords
alkali
preparation
oxybenzanthrone
yellow
solution
Prior art date
Application number
Other languages
German (de)
Inventor
Farbwerke Vorm Meiste Bruening
Original Assignee
Hoechst 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 Hoechst Ag filed Critical Hoechst Ag
Publication of CH114496A publication Critical patent/CH114496A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung     Fon        Bz-2'-ogybenzantbron.       Von den     Oxyderivaten    des     Benzanthrons     hat das in     2'-Stellung    des     Benzringes        hydroxy-          lierte        Benzanthron    besondere Bedeutung er  langt, da seine     Alkyl-    oder     Aryläther    durch  alkalische Kondensation in echte grüne     Kü-          penfarbstoffe    übergehen     (vergl.    unser     schweiz.     Patent 109,485).  



  Es ist gefunden worden, dass dieses wert  volle und bisher schwer zugängliche     Bz-2'-          oxybenzanthron    entsteht, wenn man     1'-Diazo-          oxybenzanthronanhydrid    mit reduzierenden    Mitteln behandelt.

   Das     1'-Diazooxybenzan-          thronanhydrid    kann man beispielsweise aus       2'-Nitro-1'-diazoniumsalzen    des     Benzanthrons     erhalten, indem man das     Diazoniumhydrat    in  Freiheit setzt, sei es durch Hydrolyse oder  durch Wegnahme der Säure mittelst Alkali  sulfat,     Alkaliacetat,        Bikarbonat.    Unter Ab  spaltung von salpetriger Säure geht das     2'-          Nitrobenzanthron-1'-diazoniumhydrat    leicht  in     Diazooxybenzanthronanhydrid    über.

   Die  Reaktion verläuft gemäss folgendem Schema:  
EMI0001.0030     
           Beispiel:     In eine halte Lösung von 10 Teilen       7innchloriir    in 200 Teilen Wasser und 1 5       Teilen        Ätzkali    wird unter     Rühren    die dünne  Paste des     Diazoohyanhydrides    aus 10 Teilen       o-Nitrobminobenzanthron        eingetragen,    die  zum Beispiel durch Verrühren des     Nitro-          diazosulfates    in schwach schwefelsaurer     wäs-          -i-,

  er    Lösung     bezw.    Suspension bis zur       s    -ei<B>,</B>       Wasserunlöslichkeit,    Filtration und Aus  waschen oder durch Waschen des schwer  löslichen filtrierten     Nitrodiazosulfates    mit       Alkalisulfatlösung    erhalten wird. Es tritt  lebhafte     Stickstoffentwicklung    und Auflösung  mit roter Farbe ein. Nach beendeter Reak  tion wird mit     Salzsäure    stark     angesäuert,          filtriert    und gewaschen.

   Der Niederschlag  wird nun mit     verdünntem        Alkali    in der       Wärme        digeriert,    vom Ungelösten filtriert  und aus dein Filtrate das gebildete     Oxyben-          zanthron    mit Säure gefällt. Es bildet ge  trocknet ein gelbes Pulver, das sich leicht in  Alkali mit gelbroter Farbe löst. Durch         Schütteln    mit     bimetlivlsulfat    scheidet sieh  aus dieser Lösung die     Methosyverbindung     aus, die beim Verschmelzen mit Alkali einen       Farbstoff    liefert, der aus blauer     Küpe    Baum  wolle in grünen Tönen anfärbt.



  Method of preparation Fon Bz-2'-ogybenzantbron. Of the oxyderivatives of benzanthrone, the benzanthrone hydroxylated in the 2'-position of the benz ring is of particular importance, since its alkyl or aryl ethers are converted into real green vat dyes by alkaline condensation (see our Swiss patent 109,485).



  It has been found that this valuable and previously difficult to access Bz-2'-oxybenzanthrone is formed when 1'-diazo-oxybenzanthrone anhydride is treated with reducing agents.

   The 1'-diazooxybenzanthronic anhydride can be obtained, for example, from 2'-nitro-1'-diazonium salts of benzanthrone by releasing the diazonium hydrate, either by hydrolysis or by removing the acid by means of alkali sulphate, alkali acetate, bicarbonate. With elimination of nitrous acid, the 2'-nitrobenzanthrone-1'-diazonium hydrate easily converts into diazooxybenzanthronic anhydride.

   The reaction proceeds according to the following scheme:
EMI0001.0030
           Example: The thin paste of the diazoohyanhydride made of 10 parts of o-nitrobminobenzanthrone is introduced into a permanent solution of 10 parts of tin chloride in 200 parts of water and 15 parts of caustic potash, with stirring. i-,

  he solution respectively. Suspension up to s -ei <B>, </B> water insolubility, filtration and washing out or by washing the sparingly soluble filtered nitrodiazosulfate with alkali metal sulfate solution. There is vigorous evolution of nitrogen and dissolution with a red color. After the reaction has ended, it is strongly acidified with hydrochloric acid, filtered and washed.

   The precipitate is now digested with dilute alkali in the heat, filtered to remove the undissolved material, and the oxybenzanthrone formed is precipitated from the filtrate with acid. When dried, it forms a yellow powder that dissolves easily in alkali with a yellow-red color. By shaking with bimetallic sulphate, the methosyl compound is separated from this solution, which when fused with alkali produces a dye which stains cotton in green tones from a blue vat.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Bz-2'-oxy- benzantliron, dadurch gekennzeichnet, daf;) man l'-Diazoolybenzanthronarihydrid mit re duzierenden Mitteln behandelt. Claim: Process for the preparation of Bz-2'-oxybenzantlirone, characterized in that;) l'-Diazoolybenzanthronarihydride is treated with reducing agents. Das Bz-2'- oiybenzaritliron bildet getrocknet ein gelbes Pulver, das sich leicht in Alkali mit gelb roter Farbe löst. Durch Schütteln mit Di- methy lsulfat scheidet sich aus dieser Lösung die 3ethoiyvei#biridung aus, die beim Ver schmelzen mit Alkali einen Farbstoff liefert. der aus blauer Küpe Baumwolle in grünen Tönen anfärbt. The Bz-2'-oiybenzaritliron forms a yellow powder when dried, which easily dissolves in alkali with a yellow-red color. Shaking with dimethyl sulfate separates the ethoxy coating from this solution, which when melted with alkali produces a dye. who dyes cotton in green tones from a blue vat.
CH114496D 1923-11-09 1924-10-16 Process for the preparation of Bz-2'-oxybenzanthrone. CH114496A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE114496X 1923-11-09

Publications (1)

Publication Number Publication Date
CH114496A true CH114496A (en) 1926-04-01

Family

ID=5653832

Family Applications (1)

Application Number Title Priority Date Filing Date
CH114496D CH114496A (en) 1923-11-09 1924-10-16 Process for the preparation of Bz-2'-oxybenzanthrone.

Country Status (1)

Country Link
CH (1) CH114496A (en)

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