CH217132A - 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
CH217132A
CH217132A CH217132DA CH217132A CH 217132 A CH217132 A CH 217132A CH 217132D A CH217132D A CH 217132DA CH 217132 A CH217132 A CH 217132A
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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 CH217132A publication Critical patent/CH217132A/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-Heptadecyl-benzylamin,    er  hältlich durch katalytische Reaktion von       Stearophenon    in Gegenwart von Ammoniak,

    mit     Dimethylsulfat    in die     quaternäre        Ammo-          niumverbindung    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.  



  <I>Beispiel:</I>  1     Mol.        Stearophenon,    hergestellt aus     Stea-          rinsäurechlorid    und Benzol mit Aluminium  chlorid, nach der Methode von     Friedel-Crafts,     wird in alkoholischem Ammoniak (dreifacher  Überschuss) gelöst und im     Autoklav    bei  110     Atm.    und 80 bis<B>90'</B> katalytisch hy  driert.

   Nach dem     Abfiltrieren    des     Kataly-          sators    und Abdampfen des Alkohols wird das    rohe     a-Heptadecyl-benzylamin    im     Vakuum     destilliert,     Kp.o"    210 bis 212  .  



  In 800     Volumteilen    trockenem Chlorben  zol wird 1/2     Mol.        a-Heptadecyl-benzylamin     gelöst, 120 Teile feste Soda zugesetzt     und    bei  90 bis<B>100'</B> langsam<B>130</B> Teile     Dimethyl-          sulfat    eingetropft. Nach 12     Stunden    wird  das Ganze mit dem gleichen Volumen Wasser  vermengt und das Chlorbenzol durch Wasser  dampfdestillation entfernt. Durch     Ausäthern     des Rückstandes und nachfolgende Vakuum  destillation gewinnt man das reine     a-Hepta-          decyl-benzyl-dimethylamin,    KP.,).,     223     .  



  1/2     Mol.        a-Heptadecyl-benzyl-dimethyl-          amin    wird in 800     Volumteilen    trockenem  Chlorbenzol gelöst, bei<B>1001</B> 65 Teile     Di-          methylsulfat        zugetropft    und das Ganze bei  dieser Temperatur mehrere     Stunden    gerührt.  Hierauf wird das Chlorbenzol durch Wasser  dampfdestillation entfernt     und    die klare Lö  sung der     quaternären        Ammoniumverbindung     zur Trockne verdampft.

   Es     hinterbleibt    eine  helle, zähe Paste, die in Wasser leicht lös-      lieh     ist    unter Bildung     stark    schäumender Lö  sungen.



  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, a-substituted benzylamine derivative, characterized in that one-heptadecyl-benzylamine, it is obtainable by catalytic reaction of stearophenone in the presence of ammonia

    converted into the quaternary ammonium compound with dimethyl sulfate.



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



  <I> Example: </I> 1 mol. Stearophenone, produced from stearic acid chloride and benzene with aluminum chloride, according to the Friedel-Crafts method, is dissolved in alcoholic ammonia (three-fold excess) and placed in an autoclave at 110 atm. and 80 to <B> 90 '</B> catalytically hydrogenated.

   After the catalyst has been filtered off and the alcohol has been evaporated off, the crude α-heptadecylbenzylamine is distilled in vacuo, boiling point 210 to 212.



  1/2 mole of a-heptadecylbenzylamine is dissolved in 800 parts by volume of dry chlorobenzene, 120 parts of solid soda are added and, at 90 to 100 parts, slowly 130 parts of dimethyl sulfate are added dripped in. After 12 hours, the whole thing is mixed with the same volume of water and the chlorobenzene is removed by steam distillation. The pure a-heptadecylbenzyldimethylamine, KP.,)., 223 is obtained by etherifying the residue and then vacuum distillation.



  1/2 mole of a-heptadecylbenzyldimethylamine is dissolved in 800 parts by volume of dry chlorobenzene, 65 parts of dimethyl sulfate are added dropwise at 1001 and the whole is stirred at this temperature for several hours. The chlorobenzene is then removed by steam distillation and the clear solution of the quaternary ammonium compound is evaporated to dryness.

   What remains is a light, viscous paste which is easily soluble in water with the formation of strongly foaming solutions.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines wasser löslichen, höhermolekularen, a-substituierten Benzylaminderivates, dadurch gekennzeich net, dass man a-Heptadecyl-benzylamin mit Dimethylsulfat in die quaternäre Ammonium verbindung 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. PATENT CLAIM: Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative, characterized in that α-heptadecylbenzylamine is converted into the quaternary ammonium compound with dimethyl 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.
CH217132D 1938-11-25 1938-11-25 Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. CH217132A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH217132T 1938-11-25
CH214904T 1941-12-03

Publications (1)

Publication Number Publication Date
CH217132A true CH217132A (en) 1941-09-30

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Application Number Title Priority Date Filing Date
CH217132D CH217132A (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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CH (1) CH217132A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3467708A (en) * 1965-10-21 1969-09-16 Armour Ind Chem Co Aryl-substituted aliphatic benzyl and naphthyl-methylene quaternary ammonium compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3467708A (en) * 1965-10-21 1969-09-16 Armour Ind Chem Co Aryl-substituted aliphatic benzyl and naphthyl-methylene quaternary ammonium compounds

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