CH233844A - Process for the preparation of 1-aminobenzene-4-sulfo-2-carboxylic acid. - Google Patents

Process for the preparation of 1-aminobenzene-4-sulfo-2-carboxylic acid.

Info

Publication number
CH233844A
CH233844A CH233844DA CH233844A CH 233844 A CH233844 A CH 233844A CH 233844D A CH233844D A CH 233844DA CH 233844 A CH233844 A CH 233844A
Authority
CH
Switzerland
Prior art keywords
aminobenzene
carboxylic acid
sulfo
preparation
acid
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 CH233844A publication Critical patent/CH233844A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings

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

Description

  

  Verfahren zur Herstellung der     1-Aminobenzol-4-sulfo-2-carbonsäure.       Die unmittelbare     Sulfonierung    der     An-          thranilsäure    führt bekanntlich nicht zum  erstrebten     Ziele,    da die     Carboxyl.gruppe    leicht  abgespalten wird. Deshalb wurde empfohlen,  die     Sulfonierung    der     Anthranilsäure    in Ge  genwart von organischen     Lösungsmitteln,     zweckmässig mit molekularen Mengen des       Sulfonierungsmittels        (vergl.        Patentschriften     Nr. 296941 und 307284), vorzunehmen.  



  Es wurde nun     gefunden,    dass trotz     der          leichten        Abspaltbarkeit    der     Carboxylgruppe     die einheitliche     Sulfonierung    der     Anthranil-          säureausserordentliclglatUvor,sich        geht,    wenn  man das saure Sulfat der     Anthranilsäure    auf  höhere Temperatur zweckmässig in Vakuum  erhitzt.

   Man erhält auf diese     Weise    in prak  tisch     quantitativer        Ausbeute    ein Produkt von       solcher        Reinheit,    dass es     unmittelbar    zur Her  stellung von Farbstoffen     verwendet    werden  kann.

   Die neue Arbeitsweise, deren Erfolg  nicht vorauszusehen war, bedeutet gegenüber    der Arbeitsweise der oben angeführten     Pa-          tentschriften    einen wesentlichen     Fortschritt.          Beispiel:

       Man mischt in     einer        Mühle    100 Teile       Schwefelsäure    von 98 % mit 137     Teilen          1-Aminobenzol-2-carbonsäure    so, dass     ein          feines        homogenes    Pulver     entsteht.    Dieses  füllt man auf Backbleche und backt während  12     Stunden    im Vakuum bei 200-220 .

   Die  entstandene     1-Aminobenzol-2-carbonsäure-4-          sulfonsäure        stellt    ein hellgraues Pulver dar,  das sich leicht in Laugen und     Mineralsäuren     löst,     und        kann    als solche     ohne        weiteres    ver  wendet     werden.    Man erhält zirka     9517o    Aus  beute.



  Process for the preparation of 1-aminobenzene-4-sulfo-2-carboxylic acid. As is well known, the immediate sulfonation of the anthranilic acid does not lead to the desired goal, since the carboxyl group is easily split off. It was therefore recommended to carry out the sulfonation of the anthranilic acid in the presence of organic solvents, expediently with molecular amounts of the sulfonating agent (see patents No. 296941 and 307284).



  It has now been found that, in spite of the easy cleavage of the carboxyl group, the uniform sulfonation of the anthranilic acid takes place exceptionally well if the acid sulfate of the anthranilic acid is suitably heated to a higher temperature in vacuo.

   In this way, a product of such purity that it can be used directly for the manufacture of dyes is obtained in practically quantitative yield.

   The new way of working, the success of which could not be foreseen, represents a significant advance compared to the way of working in the above-mentioned patents. Example:

       100 parts of 98% sulfuric acid are mixed with 137 parts of 1-aminobenzene-2-carboxylic acid in a mill so that a fine, homogeneous powder is formed. This is poured onto baking trays and baked for 12 hours in a vacuum at 200-220.

   The resulting 1-aminobenzene-2-carboxylic acid-4-sulfonic acid is a light gray powder that dissolves easily in alkalis and mineral acids and can be used as such without further ado. You get about 9517o harvest.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung -der 1-Amino- benzol-4-sulfo-2-carbonsäure,dadurch gekenn zeichnet, d'ass das Sulfat -der Anthranilsäure auf höhere Temperaturerhitzt wird. PATENT CLAIM: Process for the production of 1-amino-benzene-4-sulfo-2-carboxylic acid, characterized in that the sulfate of anthranilic acid is heated to a higher temperature.
CH233844D 1942-01-13 1942-01-13 Process for the preparation of 1-aminobenzene-4-sulfo-2-carboxylic acid. CH233844A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH233844T 1942-01-13

Publications (1)

Publication Number Publication Date
CH233844A true CH233844A (en) 1944-08-31

Family

ID=4458247

Family Applications (1)

Application Number Title Priority Date Filing Date
CH233844D CH233844A (en) 1942-01-13 1942-01-13 Process for the preparation of 1-aminobenzene-4-sulfo-2-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH233844A (en)

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