CH214902A - Process for the preparation of a new quaternary ammonium salt. - Google Patents

Process for the preparation of a new quaternary ammonium salt.

Info

Publication number
CH214902A
CH214902A CH214902DA CH214902A CH 214902 A CH214902 A CH 214902A CH 214902D A CH214902D A CH 214902DA CH 214902 A CH214902 A CH 214902A
Authority
CH
Switzerland
Prior art keywords
quaternary ammonium
ammonium salt
preparation
new
new quaternary
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 CH214902A publication Critical patent/CH214902A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines neuen     quaternären        Ammoniumsalzes.       Es wurde gefunden, dass ein neues     qua-          ternäres        Ammoniumsalz    der Formel  
EMI0001.0006     
    dadurch erhalten     wird,,dass    man     Pyridin    mit  der     Chlormethylverbindung    des     Distearyl-          diaminomethans    der Formel  
EMI0001.0012     
    zur Umsetzung     bringt.     



  Die neue     Verbindung    bildet einen weissen  Festkörper, der     in        Benzol    und Alkohol (lös  lich ist. Er löst sich in Wasser unter Bil  dung von Lösungen, die     beim    Schütteln    schäumen. Werden diese     Lösungen    gekocht,  dann werden sie allmählich trübe und ver  lieren ihre     Schäumkraft;    gegebenenfalls bil  det sich ein Niederschlag. Die neue Verbin  dung kann zum     Wasserabstossendmachen    von  Textilien verwendet werden.  



  Bei der praktischen Durchführung des       Verfahrens    werden zweckmässig die genannte       Chlormethylverbindung    und das     Pyridin          vermischt,    vorteilhaft in Gegenwart eines       Lösungs-    oder eines Verdünnungsmittels.  Es entwickelt sich Wärme, und es ist  vorteilhaft, das Amin langsam hinzuzufügen  und den     Reaktionsbehälter    zu kühlen.  



       Beispiel:     Das Ausgangsmaterial für dieses Bei  spiel     wird    in folgender     Weise        dargestellt:     29 Teile     Distearyldiaminomethan    (siehe  franz. Patentschrift Nr. 782330), in Form  von Pulver,     und    6     Teile        Paraformaldehyd          werden:    mit 150     Teilen    Benzol gemischt. Das      Gemisch wird gerührt und auf     GO      C er  wärmt. Trockener Chlorwasserstoff wird so  lange eingeleitet, bis, nachdem eine Probe  auf Zimmertemperatur abgekühlt wurde, sieh  nichts Festes mehr abscheidet.

   Man     lä.sst    Glas  Gemisch sich setzen, worauf es: sich in zwei  Schichten trennt. Die untere     wässrige    Schicht  wird entfernt und nicht weiter verwertet.  Das Benzol aus der     obern        Schicht    wird unter       vermindertem    Druck     abdestilliert.    Auf diese  Weise erhält man eine     Chlormethylverbin-          dung    der folgenden Formel  
EMI0002.0010     
    Sie ist ein niedrig     schmelzender,    wachsarti  ger     Festkörper.     



  Diese     Chlormethylverbindung    wird in  200 Teilen     Äthylacetat    gelöst und diese Lö  sung allmählich mit 9 Teilen     Pyridin    ge  mischt. Ein weisser Niederschlag scheidet  aus. Dieser wird     abfiltriert    und getrocknet.  Auf diese Weise erhält man das neue     qua-          ternäre        Ammoniumsalz    in Form eines weissen  Pulvers, das sich in heissem Wasser löst,  unter Bildung klarer schäumender Lösungen,  ,die bei längerem Kochen trübe werden und  zu schäumen aufhören.  



  Die Verbindung hat folgende Formel:  
EMI0002.0020     




  Process for the preparation of a new quaternary ammonium salt. It has been found that a new quaternary ammonium salt of the formula
EMI0001.0006
    is obtained by using pyridine with the chloromethyl compound of distearyl diaminomethane of the formula
EMI0001.0012
    brings to implementation.



  The new compound forms a white solid that is soluble in benzene and alcohol (. It dissolves in water to form solutions that foam when shaken. If these solutions are boiled, they gradually become cloudy and lose their foaming power; If necessary, a precipitate forms.The new compound can be used to make textiles water-repellent.



  When carrying out the process in practice, the above-mentioned chloromethyl compound and the pyridine are advantageously mixed, advantageously in the presence of a solvent or a diluent. Heat will evolve and it will be beneficial to add the amine slowly and cool the reaction vessel.



       Example: The starting material for this example is shown in the following way: 29 parts of distearyldiaminomethane (see French Patent No. 782330), in the form of powder, and 6 parts of paraformaldehyde are: mixed with 150 parts of benzene. The mixture is stirred and warmed to GO C. Dry hydrogen chloride is passed in until, after a sample has been cooled to room temperature, nothing solid can be seen.

   You let the glass mixture sit down, whereupon it: separates into two layers. The lower aqueous layer is removed and not recycled. The benzene from the upper layer is distilled off under reduced pressure. In this way, a chloromethyl compound of the following formula is obtained
EMI0002.0010
    It is a low-melting, waxy solid.



  This chloromethyl compound is dissolved in 200 parts of ethyl acetate and this solution is gradually mixed with 9 parts of pyridine. A white precipitate separates out. This is filtered off and dried. In this way, the new quaternary ammonium salt is obtained in the form of a white powder that dissolves in hot water, forming clear, foaming solutions that become cloudy and stop foaming when boiled for a long time.



  The compound has the following formula:
EMI0002.0020

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung eines neuen quaternä.ren Ammoniumsalzes der Formel EMI0002.0024 dadurch gekennzeichnet, dass man Py ridin mit der Chlormethylverbindung des Diste- aryldiaminomethans der Formel EMI0002.0030 umsetzt. Die neue Verbindung ist ein weisser Festkörper. der in Benza1 und Alkohol lös lich ist.. Er löst sieh in Wasser unter Bil dung von Lösungen, die beim Schütteln schäumen. PATENT CLAIM Process for the preparation of a new quaternary ammonium salt of the formula EMI0002.0024 characterized in that pyridine is combined with the chloromethyl compound of dis aryldiaminomethane of the formula EMI0002.0030 implements. The new connection is a white solid. which is soluble in benzene and alcohol. It dissolves in water to form solutions which foam when shaken. Werden diese Lösungen gekocht, dann werden sie allmählich trübe und ver lieren ihre Sehä:umkraft; gegebenenfalls bil det sich ein Niederschlag. Die neue Verbin dung kann zum Wasserabstossendmachen von Textilien verwendet werden. If these solutions are boiled, they gradually become cloudy and lose their vision; if necessary, a precipitate forms. The new connection can be used to make textiles water-repellent.
CH214902D 1938-07-29 1939-07-27 Process for the preparation of a new quaternary ammonium salt. CH214902A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB214902X 1938-07-29

Publications (1)

Publication Number Publication Date
CH214902A true CH214902A (en) 1941-05-31

Family

ID=10163806

Family Applications (1)

Application Number Title Priority Date Filing Date
CH214902D CH214902A (en) 1938-07-29 1939-07-27 Process for the preparation of a new quaternary ammonium salt.

Country Status (1)

Country Link
CH (1) CH214902A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE891258C (en) * 1942-09-29 1953-09-28 Hoechst Ag Process for the preparation of quaternary ammonium or isothiuronium salts

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE891258C (en) * 1942-09-29 1953-09-28 Hoechst Ag Process for the preparation of quaternary ammonium or isothiuronium salts

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