CH217134A - Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. - Google Patents

Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative.

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Publication number
CH217134A
CH217134A CH217134DA CH217134A CH 217134 A CH217134 A CH 217134A CH 217134D A CH217134D A CH 217134DA CH 217134 A CH217134 A CH 217134A
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CH
Switzerland
Prior art keywords
water
soluble
molecular weight
higher molecular
production
Prior art date
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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.)
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Publication date
Application filed by Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH217134A publication Critical patent/CH217134A/en

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Description

  

  Verfahren zur Herstellung eines wasserlöslichen,     höhermolekularen,          a-substituierten        Benzylaminderivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines wasser  löslichen,     höhermolekularen,        a-substituierten          Benzylaminderivates,    dadurch gekennzeich  net,

   dass man     a-Methyl-4-dodecylbenzylamin     mit     Dimethylsulfat        methyliert    und das er  haltene     a-Methyl-4-dodecyl-benzyldimethyl-          amin    mit     DiäthylsuHat    in die     quaternäre          Ammoniumverbindung    überführt.  



  Die neue Verbindung, eine helle, zähe  Paste, ist in Wasser leicht löslich unter Bil  dung stark schäumender Lösungen und kann  als Desinfektionsmittel verwendet werden.  



       Beispiel:     200 Teile     Laurophenon    werden mit 200  Teilen amalgamiertem Zinkblech und 400       Volumteilen    Salzsäure, hergestellt aus einem  Teil konzentrierter Säure und 2 Teilen Was  ser, am     Rückflusskühler    5 Stunden gekocht.  Nach jeder Stunde werden weitere 50     Volum-          teile    Salzsäure zugegeben. Man lässt etwas  abkühlen, trennt im Scheidetrichter das helle    <B>01</B> von der     wässrigen    Schicht ab und wäscht  es mit heissem Wasser.  



  Das im Vakuum gut     getrocknete        Dodecyl-          benzol    wird in 500     Volumteilen    Schwefel  kohlenstoff gelöst, dann werden 120 Teile  Aluminiumchlorid darin aufgeschlämmt und  langsam 100     Volumteile        Essigsäureanhydrid          zugetropft.    Das Ganze wird 10     Stunden    unter       Rückfluss    gekocht, bis die     Salzsäureentwick-          lung    beendet ist. Dann wird auf Eis ge  gossen, eventuell mit Salzsäure das ausge  schiedene     Aluminiumhydrogyd    in Lösung ge  bracht und das Ganze dampfdestilliert.

   Das  aus dem Rückstand     ausgeKtherte.4-Dodecyl-          acetophenon    hat einen $p."" 180 bis<B>270'</B>  und ist ein helles, langsam erstarrendes 01.  



  180 Teile     4-Dodecyl-acetophenon    werden  zusammen mit 180 Teilen     Ammonformiat     langsam auf 185   geheizt und über Nacht  bei dieser Temperatur gehalten. Nach dem  Verseifen der entstandenen     Formylverbin-          dung    erhält man das freie     a-Methyl-4-dodecyl-          benzylamin    als helles     0'l.    0,5     Mol.    desselben      löst man in 700     Volumteilen    trockenem  Chlorbenzol,

   fügt 120 Teile feste Soda zu  und     läBt    bei 90   langsam 130 Teile     Di-          methyIsulfat        eintropfen.    Nach 10stündigem  Rühren bei dieser Temperatur entfernt man  das ausgeschiedene Natriumsulfat durch Fil  trieren und lädt zu der klaren     Chlorbenzol-          lösung    der     Dimethylaminoverbindung    bei  100   langsam 77     Teile        Diäthylsulfat    tropfen.  Man behält die Lösung 5 Stunden bei dieser  Temperatur und bläst das Lösungsmittel mit  Wasserdampf ab.

   Aus dem Rückstand erhält  man durch     Eindampfen    die     quaternäre    Am  moniumverbindung als helle zähe Paste.



  Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. The subject of the present patent is a process for the preparation of a water-soluble, higher molecular weight, α-substituted benzylamine derivative, characterized in that

   that a-methyl-4-dodecylbenzylamine is methylated with dimethyl sulfate and the a-methyl-4-dodecyl-benzyldimethylamine that is obtained is converted into the quaternary ammonium compound with diethyl sulfate.



  The new compound, a light-colored, viscous paste, is easily soluble in water with the formation of strongly foaming solutions and can be used as a disinfectant.



       Example: 200 parts of laurophenone are boiled with 200 parts of amalgamated zinc sheet and 400 parts by volume of hydrochloric acid, prepared from one part of concentrated acid and 2 parts of water, on a reflux condenser for 5 hours. After every hour, a further 50 parts by volume of hydrochloric acid are added. Allow to cool slightly, separate the light <B> 01 </B> from the aqueous layer in a separating funnel and wash it with hot water.



  The dodecylbenzene, which has been thoroughly dried in vacuo, is dissolved in 500 parts by volume of carbon disulfide, then 120 parts of aluminum chloride are slurried in it and 100 parts by volume of acetic anhydride are slowly added dropwise. The whole is refluxed for 10 hours until the evolution of hydrochloric acid has ended. Then it is poured onto ice, possibly the precipitated aluminum hydrogen is brought into solution with hydrochloric acid and the whole thing is steam distilled.

   The 4-dodecyl acetophenone which is etherified from the residue has a $ p. "" 180 to <B> 270 '</B> and is a light-colored, slowly solidifying 01.



  180 parts of 4-dodecyl-acetophenone are slowly heated to 185 together with 180 parts of ammonium formate and kept at this temperature overnight. After saponifying the resulting formyl compound, the free α-methyl-4-dodecylbenzylamine is obtained as a light-colored oil. 0.5 mol. Of the same is dissolved in 700 parts by volume of dry chlorobenzene,

   add 120 parts of solid soda and slowly let 130 parts of dimethyl sulfate drip in at 90. After stirring for 10 hours at this temperature, the precipitated sodium sulfate is removed by filtration and 77 parts of diethyl sulfate are slowly added dropwise to the clear chlorobenzene solution of the dimethylamino compound at 100. The solution is kept at this temperature for 5 hours and the solvent is blown off with steam.

   The quaternary ammonium compound is obtained as a light, viscous paste from the residue by evaporation.

 

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines wasser löslichen, höhermolekularen, a-substituierten Benzylaminderivates, dadurch gekennzeich net, daB man a-Methyl-4-dodecyl-benzylamin mit Dimethylsulfat methyliert und das erhal tene a-Methyl-4-dodecyl-benzyldimethylamin mit Diäthylsulfat in die quaternäre Ammo- niumverbindung überführt. PATENT CLAIM: Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative, characterized in that α-methyl-4-dodecylbenzylamine is methylated with dimethyl sulfate and the α-methyl-4 obtained is obtained -dodecyl-benzyldimethylamine converted into the quaternary ammonium compound with diethyl sulfate. Die neue Verbindung, eine helle, zähe Paste, ist in Wasser leicht löslich unter Bil dung stark schäumender Lösungen und kann als Desinfektionsmittel verwendet werden. The new compound, a light-colored, viscous paste, is easily soluble in water with the formation of strongly foaming solutions and can be used as a disinfectant.
CH217134D 1938-11-25 1938-11-25 Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. CH217134A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH217134T 1938-11-25
CH214904T 1941-12-03

Publications (1)

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CH217134A true CH217134A (en) 1941-09-30

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CH217134D CH217134A (en) 1938-11-25 1938-11-25 Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative.

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2636036A (en) * 1946-12-28 1953-04-21 Onyz Oil & Chemical Company Aromatic nitrogen compounds
US2676986A (en) * 1950-02-15 1954-04-27 Onyx Oil & Chemical Company Ethylbenzyl, lauryl, dimethyl ammonium salts
US2802812A (en) * 1953-06-26 1957-08-13 L A Dreyfus Company P-alkyl styrenes and their polymers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2636036A (en) * 1946-12-28 1953-04-21 Onyz Oil & Chemical Company Aromatic nitrogen compounds
US2676986A (en) * 1950-02-15 1954-04-27 Onyx Oil & Chemical Company Ethylbenzyl, lauryl, dimethyl ammonium salts
US2802812A (en) * 1953-06-26 1957-08-13 L A Dreyfus Company P-alkyl styrenes and their polymers

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