CH236920A - Process for the preparation of a quaternary ammonium salt. - Google Patents

Process for the preparation of a quaternary ammonium salt.

Info

Publication number
CH236920A
CH236920A CH236920DA CH236920A CH 236920 A CH236920 A CH 236920A CH 236920D A CH236920D A CH 236920DA CH 236920 A CH236920 A CH 236920A
Authority
CH
Switzerland
Prior art keywords
ammonium salt
preparation
quaternary ammonium
triethylamine
reacting
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH236920A publication Critical patent/CH236920A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups

Landscapes

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

Description

  

      Yerfaluen        zur    Herstellung eines     quaternären        Aininoniumsalzes.       Im schweizerischen Patent     Nr.228215     (Zusatzpatent zum Hauptpatent Nr.

   220496)  wird ein Verfahren zur Herstellung eines       nuaternären        Ammoniumsalzes        beschrieben,     welches als wasserabstossendes Mittel für Tex  tilien geeignet ist und dadurch erhalten       #vird,    dass man     Triäthylamin    mit einer durch       U?msetzung    von     Octadecylc.arbamat    mit     Di-          chlordimethyläther    erhaltenen     Chlormethyl-          verbindung    zur     Reaktion        bringt.     



  Es wurde nun gefunden, dass das gleiche       duaternäre        Ammoniumsalz    dadurch erhalten  werden kann, dass man     Methyloloctadecy1car-          bamat    mit     Dichlordimethyläther    umsetzt und  hierauf die so gebildete     Chlormethylverbin-          dung    mit     Triäthylamin    zur Reaktion bringt.  



  Die Umsetzung des     Carbamats    mit dem       Dichlordimethyläther    wird durch Erhitzen  der Reagenzien auf eine mässig hohe. Tempe  ratur zustande gebracht.  



  Die Reaktion der     Chlormethylverbindung     mit dem     Triäthylamin    erfolgt durch Mischen  der Reagenzien zweckmässig in Gegenwart    eines     Verdünnungsmittels,    wie zum Beispiel  Benzol oder     Äthylendichlorid.    Dabei wird  Wärme entwickelt. Es ist somit zweckmässig,  die Zugabe des     T'riäthylamins    langsam vor  zunehmen und das Reaktionsgemisch durch  Kühlen des Reaktionsgefässes kalt zu halten.  



  Das nachstehende Beispiel möge die Er  findung erläutern.    <I>Beispiel:</I>  <B>2 0</B>     Teile        Methyloloctadecylcarbamat        und     7 Teile     Dichlordimethyläther    werden ge  mischt und     zusammen    unter     Rückfluss    wäh  rend 2 Stunden erhitzt. Das so erhaltene Pro  dukt wird     hierauf    während 1     Stunde    auf 100  C  bei 15 mm Druck erhitzt, um es von unver  ändertem     Dichlordimethyläther    zu befreien.  Der     zurückbleibende,    wachsartige Festkörper  stellt eine     Chlormethylverbindung    dar.  



  Dieses Produkt wird mit 50 Teilen     Athy-          lendichlorid    vermischt und hierauf mit 6,4       TeilenTriäthylamin        allmählich    versetzt. Nun      wird das     quaternäre    Salz durch     Abdestillie-          ren    des     Äthylendichlorids    unter     subatmo-          sphärischem    Druck abgetrennt. Dabei hinter  bleibt ein weisser Festkörper, der sich in  Wasser unter Bildung einer beim     Schütteln     schäumenden Lösung löst.

   Wird diese Lö  sung gekocht, so wird sie allmählich trübe  und     verliert    ihre     Fähibkeit,    zu     schäumen.  



      Yerfaluen for the production of a quaternary ammonium salt. In the Swiss patent 228215 (additional patent to the main patent no.

   220496) describes a process for the production of a natural ammonium salt, which is suitable as a water-repellent agent for textiles and is obtained by reacting triethylamine with a chloromethyl compound obtained by reacting octadecyl carbamate with dichlorodimethyl ether brings.



  It has now been found that the same duaternary ammonium salt can be obtained by reacting methyl octadecylcarbamate with dichlorodimethyl ether and then reacting the chloromethyl compound thus formed with triethylamine.



  The conversion of the carbamate with the dichlorodimethyl ether is moderately high by heating the reagents. Temperature brought about.



  The reaction of the chloromethyl compound with the triethylamine is carried out by mixing the reagents, conveniently in the presence of a diluent, such as benzene or ethylene dichloride. Heat is developed in the process. It is therefore advisable to slowly add the triethylamine and to keep the reaction mixture cold by cooling the reaction vessel.



  Let the following example explain the invention. <I> Example: </I> <B> 2 0 </B> parts of methyl octadecyl carbamate and 7 parts of dichlorodimethyl ether are mixed and heated together under reflux for 2 hours. The product thus obtained is then heated to 100 ° C. at 15 mm pressure for 1 hour in order to free it from unchanged dichlorodimethyl ether. The waxy solid that remains is a chloromethyl compound.



  This product is mixed with 50 parts of ethylene dichloride and then 6.4 parts of triethylamine are gradually added. The quaternary salt is now separated off by distilling off the ethylene dichloride under subatmospheric pressure. A white solid remains behind, which dissolves in water to form a foaming solution when shaken.

   When this solution is boiled, it gradually becomes cloudy and loses its ability to foam.

Claims (1)

1' ATENTANSPRUCII Verfahren zur Herstellung eines quater- nären Amnionüunsalzes, dadurch gekenn zeichnet. dass manilethvloloctadecylearbamat mit Dichlordimethvläther umsetzt. und hier auf die so gebildete Chlormethylverbindung mit Triäthylamin zur Reaktion bringt. 1 'ATENTANSPRUCII Process for the production of a quaternary amniotic salt, characterized thereby. that manilethvloloctadecylearbamat reacts with dichlorodimethane. and here reacts the chloromethyl compound thus formed with triethylamine.
CH236920D 1940-02-16 1941-02-17 Process for the preparation of a quaternary ammonium salt. CH236920A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB236920X 1940-02-16
CH220496T 1941-02-17

Publications (1)

Publication Number Publication Date
CH236920A true CH236920A (en) 1945-03-15

Family

ID=25726453

Family Applications (1)

Application Number Title Priority Date Filing Date
CH236920D CH236920A (en) 1940-02-16 1941-02-17 Process for the preparation of a quaternary ammonium salt.

Country Status (1)

Country Link
CH (1) CH236920A (en)

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