CH242153A - Process for the production of a new sulfamide derivative. - Google Patents

Process for the production of a new sulfamide derivative.

Info

Publication number
CH242153A
CH242153A CH242153DA CH242153A CH 242153 A CH242153 A CH 242153A CH 242153D A CH242153D A CH 242153DA CH 242153 A CH242153 A CH 242153A
Authority
CH
Switzerland
Prior art keywords
tetrahydronaphthalene
sulfamide derivative
production
new
new sulfamide
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH242153A publication Critical patent/CH242153A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

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

Description

  

  Verfahren zur Herstellung eines neuen     Sulfamidderivates.       Es wurde gefunden, dass man zu     einem     neuen     Sulfamidderivat    gelangt, wenn man       ar-2-Chlormethyl-tetrahydronaphthalin    auf  das Umsetzungsprodukt von     Natriumform-          aldehydbisulfit    mit der     Mischung    aus den       isomeren        Sulfamiden,    wie sie durch Behan  deln von     Tetrahydronaphthalin    mit     Chlor-          sulfonsäure    und nachfolgende Umsetzung mit  Ammoniak erhältlich ist,     einwirken    lässt.

    



  Die Umsetzung mit dem     ar-2-Chlor-          methyl-tetrahydronaphthalin    wird zweck  mässig in der Wärme, z. B. bei 60-70 , vor  teilhaft unter     Züsatz    von säurebindenden  Mitteln, beispielsweise in Gegenwart von  wässeriger     Natriumhydrogydlösung,    vorge  nommen.  



  Das neue     Sulfamidderivat    bildet     eine     leicht     pulverisierbare,    feste Masse, die von  warmem Wasser zu einer klaren, schäumen  den Lösung - von guter     Waschkraft    auf  genommen wird. Es kann als     Tegtilhilfsstoff,     z. B. als Waschmittel, Anwendung finden.

      <I>Beispiel:</I>  Man löst 10     Gewichtsteile    des durch Um  setzung von     Tetrahydronaphthalin-sulfamid     mit     Natriumformaldehyd-bisulfit    hergestell  ten Erzeugnisses in 20     Volumteilen    Wasser  und lässt 4,4 Gewichtsteile     ar-2-Chlormethyl-          tetrahydronaphthalin    und 3,9 Gewichtsteile  30%ige     Natriumhydrogydlösung    bei 65 bis  70  im Laufe von 2     Stunden    unter Rühren       hinzufliessen.    Man rührt bei der angegebenen       Temperatur    nach, bis das Umsetzungsgut in  warmem Wasser klar löslich ist, was nach  kurzer Zeit der Fall ist,

   neutralisiert darauf  mit Schwefelsäure und verdampft zur  Trockne. Das so     erhaltene        Erzeugnis,    eine  leicht     pulverisierbare,    feste Masse,     wird    von       warmem    Wasser zu einer klaren, schäumen  den Lösung von guter Waschkraft auf  genommen.  



  Das als Ausgangsmaterial verwendete  Umsetzungsprodukt aus     Tetrahydronaph-          thalin-sulfamid    und     Natriumformaldehyd-          bisulfit    wurde durch Erhitzen von 21 Ge-           wichtsteilen        Tetrahydronaphthalinsulfamid     (Mischung aus den     isomeren        Sulfamiden,    wie  sie durch Behandeln von     Tetrahydronaph-          thalin    mit     Chlorsulfonsäure    und nachfolgende  Umsetzung mit Ammoniak erhältlich ist),

    mit 20 Gewichtsteilen     Natriumformaldehyd-          bisulfit    und 1,2 Gewichtsteilen     Diamylamin     (als Katalysator     wirkend)    während etwa  1 Stunde auf 160-165  hergestellt.



  Process for the production of a new sulfamide derivative. It has been found that a new sulfamide derivative is obtained if ar-2-chloromethyl-tetrahydronaphthalene is added to the reaction product of sodium formaldehyde bisulfite with the mixture of the isomeric sulfamides, as obtained by treating tetrahydronaphthalene with chlorosulfonic acid and subsequent reaction is available with ammonia.

    



  The reaction with the ar-2-chloromethyl-tetrahydronaphthalene is expediently in the heat, for. B. at 60-70, before geous with the addition of acid-binding agents, for example in the presence of aqueous sodium hydrogen solution, made before.



  The new sulfamide derivative forms an easily pulverizable, solid mass that is absorbed by warm water into a clear, foaming solution - with good washing power. It can be used as a Tegtilhilfsstoff, z. B. as a detergent, use.

      <I> Example: </I> 10 parts by weight of the product produced by reaction of tetrahydronaphthalene sulfamide with sodium formaldehyde bisulfite are dissolved in 20 parts by volume of water and 4.4 parts by weight of ar-2-chloromethyl tetrahydronaphthalene and 3.9 parts by weight are left Add 30% sodium hydrogen solution at 65 to 70 in the course of 2 hours while stirring. The mixture is stirred at the specified temperature until the reaction material is clearly soluble in warm water, which is the case after a short time,

   then neutralized with sulfuric acid and evaporated to dryness. The product thus obtained, an easily pulverizable, solid mass, is taken by warm water to a clear, foaming solution of good detergency.



  The reaction product of tetrahydronaphthalene sulfamide and sodium formaldehyde bisulfite used as starting material was obtained by heating 21 parts by weight of tetrahydronaphthalene sulfamide (mixture of the isomeric sulfamides, as can be obtained by treating tetrahydronaphthalene with chlorosulfonic acid and subsequent reaction with ammonia),

    with 20 parts by weight of sodium formaldehyde bisulfite and 1.2 parts by weight of diamylamine (acting as a catalyst) to 160-165 for about 1 hour.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Sulfamidderivates, dadurch gekennzeichnet, dass man ar-2-Chlorinethyl-tetrahydronaph- thalin auf das Umsetzungsprodukt von Na- triumformaldehydbisulfit mit der Mischung aus den isomeren Sulfamiden, wie sie durch Behandeln von Tetrahydronaphthalin mit Chlorsulfonsäure und nachfolgende Um setzung mit Ammoniak erhältlich ist, ein wirken lässt. PATENT CLAIM: Process for the production of a new sulfamide derivative, characterized in that ar-2-chloroethyl-tetrahydronaphthalene is added to the reaction product of sodium formaldehyde bisulfite with the mixture of the isomeric sulfamides, as is achieved by treating tetrahydronaphthalene with chlorosulfonic acid and subsequent reaction with ammonia is available, one can act. Das neue Sulfamidderivat bildet eine leicht pulverisierbare, feste Masse, die von warmem Wasser zu einer klaren, schäumen den Lösung von guter Waschkraft auf genommen wird. Es kann als Textilhilfsstoff, z. B. als Waschmittel, Anwendung finden. LTNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man in Gegenwart eines säurebindenden Mittels arbeitet. The new sulfamide derivative forms an easily pulverizable, solid mass that is absorbed by warm water into a clear, foaming solution with good detergency. It can be used as a textile auxiliary, e.g. B. as a detergent, use. Claim: Process according to claim, characterized in that one works in the presence of an acid-binding agent.
CH242153D 1942-01-19 1942-01-19 Process for the production of a new sulfamide derivative. CH242153A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH242153T 1942-01-19

Publications (1)

Publication Number Publication Date
CH242153A true CH242153A (en) 1946-04-30

Family

ID=4462809

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242153D CH242153A (en) 1942-01-19 1942-01-19 Process for the production of a new sulfamide derivative.

Country Status (1)

Country Link
CH (1) CH242153A (en)

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