CH303518A - Process for the preparation of a mononitroaryl vinyl sulfone. - Google Patents

Process for the preparation of a mononitroaryl vinyl sulfone.

Info

Publication number
CH303518A
CH303518A CH303518DA CH303518A CH 303518 A CH303518 A CH 303518A CH 303518D A CH303518D A CH 303518DA CH 303518 A CH303518 A CH 303518A
Authority
CH
Switzerland
Prior art keywords
mononitroaryl
vinyl sulfone
preparation
sulfone
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Farbwerke Hoechst Akt 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 CH303518A publication Critical patent/CH303518A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings

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

Description

  

      Verfahren   <B>zur Darstellung eines</B>     Mononitroarylvinylsulfons.            Gegenstand    des Hauptpatentes ist ein Ver  fahren     mir    Herstellung eines     Mononitroaryl-          vinylsulfons,    das dadurch gekennzeichnet ist,  dass man auf     Phenylvinylsulfon    nitrierende       .Mittel    einwirken lässt und das gebildete     Nitro-          lihenylvinyIsulfon        isoliert.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren mir Herstellung     eines        Mono-          iiit.roa.rvlvinylsulfons,    das dadurch     gekenn-          zeiehnet    ist, dass man auf     a-Bromvinylphenyl-          smlfon    nitrierende Mittel einwirken lässt und    das gebildete     a-Bromvinylnitrophenylsulfon          isoliert.     



  Das so erhaltene neue     Bromvinylnitro-          phenybulfon    ist ein schwach gelbes     Puver,    ist  in Wasser unlöslich, lässt sich aus     Tetrachlor-          kohlenstoff        umkristallisieren    Lind schmilzt  dann bei 91-92 . Es lässt sich zu dem     a-          BromvinylaminophenylsuHon        reduzieren    und  bildet daher ein     wichtiges        Zwischenprodukt     für die Herstellung von Farbstoffen. Darüber  hinaus eignet es sich als Schädlingsbekämp  fungsmittel.

           Beispiel:     24,7     Gewichtsteile        a-Bromvinylphenylsulfon    der     wahrscheinlichen    Formel  
EMI0001.0036     
    (erhältlich durch Abspaltung von Bromwas  serstoff aus     a-ss-Dibromäthylphenylsulfon)     werden in 50     Volumteile        Sch-#vefelsäuremono-          hydrat    bei 10-15  eingerührt.

   Dann wird bei  gleicher Temperatur eine aus 6,3     Gewichts-          teilen        100%iger        Salpetersäure        und        14,7        Ge-          wichtsteilen    konzentrierter Schwefelsäure be  reitete     Nitriersäure    langsam     hinzufliessen    ge  lassen.

   Nach     kurzem        Nachrühren    wird das         Reaktionsgemisch        auf    Eiswasser     gegossen,    die       ausgeschiedene    schwach gelbe     Verbindung    ab  gesaugt und mit     Wasser    neutral gewaschen.

    Das in einer Ausbeute von 28,5     Gewichtstei-          len    anfallende     -a-Bromvinylnitrophenylsulfon          schmilzt    nach dem     Umlösen    aus     Tetrachlor-          kohlenstoff    bei 91-92  und hat die wahr  scheinliche Formel:    
EMI0002.0001     




      Process for the preparation of a mononitroaryl vinyl sulfone. The subject of the main patent is a process with the production of a mononitroaryl vinyl sulfone, which is characterized in that nitrating agents are allowed to act on phenyl vinyl sulfone and the nitro-lihenyl vinyl sulfone formed is isolated.



  The subject of the present patent is a process with the production of a mono-iiit.roa.rvlvinylsulfons which is characterized in that a-bromovinylphenylsulfone nitrating agents are allowed to act and the a-bromovinylnitrophenylsulfone formed is isolated.



  The new bromovinylnitrophenybulfone obtained in this way is a pale yellow powder, is insoluble in water, can be recrystallized from carbon tetrachloride and then melts at 91-92. It can be reduced to the α-bromovinylaminophenyl sulfone and is therefore an important intermediate for the production of dyes. It is also suitable as a pest control agent.

           Example: 24.7 parts by weight of a-bromovinylphenyl sulfone of the likely formula
EMI0001.0036
    (obtainable by splitting off hydrogen bromide from α-β-dibromoethylphenyl sulfone) are stirred into 50 parts by volume of sulfuric acid monohydrate at 10-15.

   Then, at the same temperature, a nitrating acid prepared from 6.3 parts by weight of 100% nitric acid and 14.7 parts by weight of concentrated sulfuric acid is allowed to slowly flow in.

   After stirring for a short time, the reaction mixture is poured onto ice water, the pale yellow compound which has separated out is suctioned off and washed neutral with water.

    The -a-bromovinylnitrophenylsulfone, which is obtained in a yield of 28.5 parts by weight, melts at 91-92 after dissolving from carbon tetrachloride and has the probable formula:
EMI0002.0001

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Mono- nitroarylvinyIsulfons, dadurch gekennzeich- net, dass man auf a-Bromvinylphenylsulfon nitrierende Mittel einwirken lässt und das ge bildete a-Bromvinylnitrophen3-lsulfon isoliert. PATENT CLAIM: Process for the production of a mononitroarylvinyisulphone, characterized in that a-bromovinylphenylsulphone nitrating agents are allowed to act and the α-bromovinylnitrophen3-isulphone formed is isolated. Das so erhaltene neue Bromvinylnitrophe- nylsulfon ist ein schwach gelbes Pulver, ist in Wasser unlöslieh, lässt sieh aus Tetrachlor- kohlenstoff umkristallisieren und sebmilzt dann bei 91-92 . The new bromovinylnitrophenylsulfone obtained in this way is a pale yellow powder, is insoluble in water, can be recrystallized from carbon tetrachloride and then melts at 91-92.
CH303518D 1942-01-29 1943-10-15 Process for the preparation of a mononitroaryl vinyl sulfone. CH303518A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE303518X 1942-01-29
CH297403T 1943-10-15

Publications (1)

Publication Number Publication Date
CH303518A true CH303518A (en) 1954-11-30

Family

ID=25733832

Family Applications (1)

Application Number Title Priority Date Filing Date
CH303518D CH303518A (en) 1942-01-29 1943-10-15 Process for the preparation of a mononitroaryl vinyl sulfone.

Country Status (1)

Country Link
CH (1) CH303518A (en)

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