CH178942A - Process for the production of a new intermediate product. - Google Patents

Process for the production of a new intermediate product.

Info

Publication number
CH178942A
CH178942A CH178942DA CH178942A CH 178942 A CH178942 A CH 178942A CH 178942D A CH178942D A CH 178942DA CH 178942 A CH178942 A CH 178942A
Authority
CH
Switzerland
Prior art keywords
sulfuric acid
product
mixture
production
potassium hydroxide
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 CH178942A publication Critical patent/CH178942A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur     Herstellun,    eines neuen     Zwischenproduktes.       Es wurde gefunden, dass man ein neues  Zwischenprodukt für die Herstellung von       Farbstoffen    erhält, wenn man das Gemisch  der     Methylbenzanthrone,    die der allgemeinen  Formel  
EMI0001.0005     
    entsprechen, in welcher zwei x für Wasser  stoffatome und das dritte x für eine     Methyl-          gruppe    stehen und das erhalten wird durch  Entfernen des     2-älethylbenzanthrons    aus dem       Benzanthrongemisch,    das durch Einwirken  lassen von Glyzerin und Schwefelsäure auf       2-Methylanthraclrinorr    entsteht,

   in Gegenwart  einer Schwefelsäure, deren Gehalt 95  /o  nicht übersteigt, mit Brom zu einem Mono  bromierungsprodukt     bromiert.       Das neue Produkt löst sich in Schwefel  säure mit roter Farbe und schwach gelber  Fluoreszenz, durch Kondensation mit     1-Amino-          anthrachinon    und Verschmelzen des Konden  sationsproduktes mit alkoholischem Kalium  hydroxyd wird es in einen     olivfärbenden          Küpenfarbstoff,    durch Behandeln mit Schwe  fel und Verschmelzen des so erhaltenen  Bz' -     Bz"    -     Dibenzanthronylsulfidgemisches     mit alkoholischem     Kaliumhydroxyd    wird es  in einen,

   in sehr reinen     violettblauen    Tönen  färbenden,     Küpenfarbstoff    umgewandelt.  



  <I>Beispiel:</I>  100 Teile des     Gerniscbes    der     Methylben-          zanthrone,    die der allgemeinen Formel  
EMI0001.0024     
      in welcher zwei x für     Wasserstoffatome    und  das dritte x für eine     Methylgruppe    stehen,  entsprechen, werden in 1000 Teilen 90     o/oiger     Schwefelsäure kalt gelöst und bei<B>55"</B> mit  72 Teilen Brom versetzt.

   Man hält 4 Stun  den bei dieser Temperatur, kühlt ab, trägt  auf eine     Mischung    von Eis und     Natrium-          bisulfitlösung    aus,     filtriert,    wäscht mit Wasser  neutral und trocknet.     11T    an erhält ein gelb  olives Pulver, dessen Bromgehalt annähernd  demjenigen eines     Monobrommethylbenzan-          throns    entspricht.



  Process for the production of a new intermediate product. It has been found that a new intermediate product for the preparation of dyes is obtained if one uses the mixture of methylbenzanthrones corresponding to the general formula
EMI0001.0005
    in which two x stand for hydrogen atoms and the third x stand for a methyl group and this is obtained by removing the 2-ethylbenzanthrone from the benzanthrone mixture, which is formed by allowing glycerine and sulfuric acid to act on 2-methylanthraclrinorr,

   brominated with bromine in the presence of a sulfuric acid, the content of which does not exceed 95%, to give a monobromination product. The new product dissolves in sulfuric acid with a red color and pale yellow fluorescence, by condensation with 1-amino anthraquinone and fusing of the condensation product with alcoholic potassium hydroxide, it becomes an olive-colored vat dye, by treating with sulfur and fusing the resultant Bz '- Bz "- Dibenzanthronylsulfidgemisches with alcoholic potassium hydroxide it is in a,

   transformed into very pure purple-blue tones, vat dye.



  <I> Example: </I> 100 parts of the mixture of methylbenzanthrones, that of the general formula
EMI0001.0024
      in which two x stand for hydrogen atoms and the third x stand for a methyl group, are dissolved in 1000 parts of 90% sulfuric acid in the cold, and 72 parts of bromine are added at 55 ".

   It is kept for 4 hours at this temperature, cooled, poured onto a mixture of ice and sodium bisulfite solution, filtered, washed neutral with water and dried. 11T an receives a yellow olive powder, the bromine content of which corresponds approximately to that of a monobromomethylbenzanthrone.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Zwischenproduktes, dadurch gekennzeichnet, dass man das Gemisch der Methylbenzan- throne; die der allgemeinen Formel EMI0002.0015 entsprechen, in welcher zwei x für Wasser stoffatome und das dritte x für eine Methyl- gruppe stehen und das erhalten wird durch Entfernen des 2-Methylbenzanthrons aus dem Benzanthrongemisch, das durch Einwirken lassen von Glyzerin und Schwefelsäure auf 2-Methylanthrachinon entsteht, PATENT CLAIM: Process for the production of a new intermediate product, characterized in that the mixture of methylbenzan thrones; that of the general formula EMI0002.0015 in which two x stand for hydrogen atoms and the third x stands for a methyl group and this is obtained by removing the 2-methylbenzanthrone from the benzanthrone mixture, which is formed by allowing glycerol and sulfuric acid to act on 2-methylanthraquinone, in Gegenwart einer Schwefelsäure, deren Gehalt 95 % nicht übersteigt, mit Brom zu einem Monobromie- rungsprodukt bromiert. Das neue Produkt löst sich in Schwefelsäure mit roter Farbe und schwach gelber Fluor eszenz, in the presence of a sulfuric acid, the content of which does not exceed 95%, brominated with bromine to form a monobromination product. The new product dissolves in sulfuric acid with a red color and pale yellow fluorescence, durch Kondensation mit 1-Amino- anthrachinon und Versclicnelzen des Konden sationsproduktes mit alkoholischem Kalium hydroxyd wird es in einen olivfärbenden Küpenfarbstoff, durch Behandeln mit Schwefel undVerschmelzen des so erhaltenen Bzi-Bzi'- Dibenzanthroriylsulfidgemisches mit alkoholi schem Kaliumhydroxyd wird es in einen, in sehr reinen violettblauen Tönen färbenden, Küpenfarbstoff umgewandelt. by condensation with 1-amino anthraquinone and trapping of the condensation product with alcoholic potassium hydroxide it becomes an olive-coloring vat dye, by treating with sulfur and melting the resulting Bzi-Bzi'-dibenzanthroriyl sulfide mixture with alcoholic potassium hydroxide it becomes very pure violet-blue tones, transformed into vat dye.
CH178942D 1934-03-17 1934-03-17 Process for the production of a new intermediate product. CH178942A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH176020T 1934-03-17
CH178942T 1934-03-17

Publications (1)

Publication Number Publication Date
CH178942A true CH178942A (en) 1935-08-15

Family

ID=25719775

Family Applications (1)

Application Number Title Priority Date Filing Date
CH178942D CH178942A (en) 1934-03-17 1934-03-17 Process for the production of a new intermediate product.

Country Status (1)

Country Link
CH (1) CH178942A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2456589A (en) * 1944-03-23 1948-12-14 American Cyanamid Co Gray vat dyestuffs and method of making the same
EP0005757A1 (en) * 1978-05-26 1979-12-12 Bayer Ag Process for preparing benzanthrones
US4812393A (en) * 1986-01-31 1989-03-14 Eastman Kodak Company Fluorescent dyes and biological and analytical uses thereof
US4927927A (en) * 1986-01-31 1990-05-22 Eastman Kodak Company Fluorescent dyes and biological and analytical uses thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2456589A (en) * 1944-03-23 1948-12-14 American Cyanamid Co Gray vat dyestuffs and method of making the same
EP0005757A1 (en) * 1978-05-26 1979-12-12 Bayer Ag Process for preparing benzanthrones
US4812393A (en) * 1986-01-31 1989-03-14 Eastman Kodak Company Fluorescent dyes and biological and analytical uses thereof
US4927927A (en) * 1986-01-31 1990-05-22 Eastman Kodak Company Fluorescent dyes and biological and analytical uses thereof

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