CH213837A - Process for the preparation of a quaternary aminobenzylacylamine. - Google Patents

Process for the preparation of a quaternary aminobenzylacylamine.

Info

Publication number
CH213837A
CH213837A CH213837DA CH213837A CH 213837 A CH213837 A CH 213837A CH 213837D A CH213837D A CH 213837DA CH 213837 A CH213837 A CH 213837A
Authority
CH
Switzerland
Prior art keywords
quaternary
aminobenzylacylamine
preparation
water
parts
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH213837A publication Critical patent/CH213837A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/06—Hydrogenosulfates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

  

  Verfahren zur Herstellung eines     quaternären        Aminobenzylacylamins.       Es wurde gefunden, dass man neue     Amino-          benzylacylamine    erhält, wenn man Verbin  dungen der Formel       Ri-NH-COORa     worin     Ri    einen     höhermolekularen,        aliphati-          schen    oder     alicyclischen        Kohlenwasserstoffrest     mit mehr als 5     C-Atomen    und R:

  ,     einen    Al  kylrest bedeuten, mit     Aminobenzylaminoaryl-          verbindungen    in Gegenwart von Ammoniak    umsetzt     und    durch Behandlung mit     Alkylie-          rungsmitteln    nach üblichem Verfahren die  erhaltenen neuen Verbindungen in die     quater-          nären    Derivate überführt.

   Es entstehen wert  volle Netz-,     Dispergier-    und     Emulgiermittel,     insbesondere aber     Weichmachungsmittel        für     Baumwolle oder     umgefällte        Cellulose.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines     quater-          nären        Aminobenzylacylamins    der Formel  
EMI0001.0030     
    dadurch gekennzeichnet, dass man     Heptadecyl-          carbaminsäuremethylester    mit     Dimethylamino-          benzylsulfanilsäure    in Gegenwart von Am  moniak umsetzt und das erhaltene Konden  sationsprodukt mit     Dimethylsulfat    in die       quaternäre    Verbindung     überführt.     



  Die neue     quaternäre    Verbindung, eine  braune Paste, ist in Wasser klar löslich und  eignet sich zur     Verwendung    als Weich-         machungsmittel        für    Baumwolle oder umge  fällte     Cellulose.     



  <I>Beispiel:</I>  89 Teile     Heptadecylcarbaminsäuremethyl-          ester,    110 Teile     Dimethylaminobenzylsulfanil-          säure        92,1        %        und        500        Volumteile        Ammoniak          25        %        werden        in        einem        rotierenden        Äuto-          klaven    6 Stunden auf<B>1600</B>     

  erhitzt.    Nach      dem Erkalten wird der     Autoklaveninhalt    ab  gesaugt. Der Rückstand wird mehrere Male  mit heissem Wasser gewaschen und durch       Schmelzen    im Vakuum     getrocknet.    '-Man     er-          5    hält 110 Teile einer     wachsartigen    Masse.  



  41 Teile dieses Kondensationsproduktes  und 14 Teile     Dimethvlsulfat    werden über  -Nacht auf dem Wasserbade gerührt, worauf    das Produkt klar wasserlöslich geworden ist.  Man erhält eine braune Paste, die klar was  serlöslich ist.



  Process for the preparation of a quaternary aminobenzylacylamine. It has been found that new aminobenzylacylamines are obtained if compounds of the formula Ri-NH-COORa in which Ri is a higher molecular weight, aliphatic or alicyclic hydrocarbon radical with more than 5 carbon atoms and R:

  , mean an alkyl radical, reacts with aminobenzylaminoaryl compounds in the presence of ammonia and converts the new compounds obtained into the quaternary derivatives by treatment with alkylating agents according to a customary method.

   Valuable wetting agents, dispersants and emulsifiers are produced, but in particular softeners for cotton or reprecipitated cellulose.



  The present patent relates to a process for the preparation of a quaternary aminobenzylacylamine of the formula
EMI0001.0030
    characterized in that heptadecyl carbamic acid methyl ester is reacted with dimethylamino benzylsulfanilic acid in the presence of ammonia and the resulting condensation product is converted into the quaternary compound with dimethyl sulfate.



  The new quaternary compound, a brown paste, is clearly soluble in water and is suitable for use as a softener for cotton or reprecipitated cellulose.



  <I> Example: </I> 89 parts of methyl heptadecylcarbamate, 110 parts of dimethylaminobenzylsulfanilic acid 92.1% and 500 parts by volume of ammonia 25% are heated to 1600 for 6 hours in a rotating autoclave

  heated. After cooling, the contents of the autoclave are sucked off. The residue is washed several times with hot water and dried by melting in vacuo. 110 parts of a waxy mass are obtained.



  41 parts of this condensation product and 14 parts of dimethyl sulfate are stirred overnight on the water bath, whereupon the product has become clearly soluble in water. A brown paste is obtained which is clearly soluble in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines quater- nären Aminobenzylacylamins der Foinnel EMI0002.0013 dadurch gekennzeichnet, dass man Heptadecyl- carbaminsä uremethylester mit Dimethylamino- benzylsulfanilsäure in Gegenwart von Am moniak umsetzt und das erhaltene Konden sationsprodukt mit Dimethylsulfat in die quaternäre Verbindung überführt. PATENT CLAIM: Process for the production of a quaternary aminobenzylacylamine of the Foinnel EMI0002.0013 characterized in that methyl heptadecyl carbamate is reacted with dimethylamino benzylsulfanilic acid in the presence of ammonia and the condensation product obtained is converted into the quaternary compound with dimethyl sulfate. Die neue quaternäre Verbindung, eine braune Paste, ist in Wasser klar löslich und eignet sich zur Verwendung als Weich- machungsmittel für Baumwolle oder umge fällte Cellulose. The new quaternary compound, a brown paste, is clearly soluble in water and is suitable for use as a softener for cotton or reprecipitated cellulose.
CH213837D 1939-03-16 1939-03-16 Process for the preparation of a quaternary aminobenzylacylamine. CH213837A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH199452T 1939-03-16
CH213837T 1939-03-16

Publications (1)

Publication Number Publication Date
CH213837A true CH213837A (en) 1941-03-15

Family

ID=25723274

Family Applications (1)

Application Number Title Priority Date Filing Date
CH213837D CH213837A (en) 1939-03-16 1939-03-16 Process for the preparation of a quaternary aminobenzylacylamine.

Country Status (1)

Country Link
CH (1) CH213837A (en)

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