CH130881A - Process for the preparation of a quaternary ammonium compound. - Google Patents

Process for the preparation of a quaternary ammonium compound.

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Publication number
CH130881A
CH130881A CH130881DA CH130881A CH 130881 A CH130881 A CH 130881A CH 130881D A CH130881D A CH 130881DA CH 130881 A CH130881 A CH 130881A
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CH
Switzerland
Prior art keywords
salts
base
ointment
water
preparation
Prior art date
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German (de)
Inventor
Gesellschaft Fuer Chemis Basel
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Chem Ind Basel
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Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH130881A publication Critical patent/CH130881A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung einer     quaternären        Ammoniumverbindung.       Es wurde gefunden,     dass    man zu einer       quaternären        Ammoniumverbindung    gelangen  kann, indem man     Oleyl-diäthyl-äthylendiamiii     der Formel  <B>C, CO.</B>     NH.        CH-,        C1I2.   <B>N</B>     (CII-15)2     mit reaktionsfähigen     Ivlethylestern    umsetzt  und aus den erhaltenen Salzen die Base  nach üblichen Methoden in Freiheit setzt-,.  



  Das     -Methyl-diäthv1-olev   <B>1</B>       ja.m'doäthyl-ain-          moniumhydroxyd    stellt eine dicke, salben  artige Masse dar, die in Wasser oder<B>Al-</B>  kohol leicht löslich ist. Die verdünnte wäs  serige Lösung reagiert stark alkalisch. Mit  Säuren gibt die Base in Wasser und orga  nischen Lösungsmitteln leicht lösliche, neu  trale Salze, welche in wasserfreiem Zu  stande ebenfalls salbenartige     Ma.ssen    bilden  Sowohl die freie Base, wie ihre Salze be  sitzen in wässeriger Lösung starkes Schaum  vermögen.  



  Die neue Verbindung soll zu technischen  Zwecken, zum Beispiel als Benetzungs-    mittel oder als Zusatz zu Farbbädern, Ver  wendung finden.  



  <I>Beispiel<B>1:</B></I>  <B>380</B> Teile     Oleyl-diäthyl#äthylendiamin     werden mit 142 Teilen     Jodmethyl    gemischt.  Unter starker     Wärmeentwkklung    tritt Um  setzung ein. Man löst das entstandene     sal-          bena.Hige        Jodmethylat    in Wasser auf, setzt  die Base durch Zugabe von<B>150</B> Teilen frisch  gefälltem     Süberoxyd    in Freiheit und     ver-          da,mpft    die von     den    Silbersalzen befreite Lö  sung.

   Das     Methyl-diäthvl-olc--\,#lamido,#thvl-          ammoniumhydroxyd        hinierblei#t    als     salbe"n-.     artige Masse.  



  <I>Beispiel 2:</I>  <B>380</B> Teile     Oleyl-diät.'hyl-äthylendiamin     werden mit<B>126</B> Teilen     DimetliyIsulfat    und  4000 Teilen Wasser kräftig verrührt. Nach  zirka einer Stunde ist die Reaktion beendet  und das     Methyl-diä;thyl-oleylamidoäthyl-am-          monium-suliometliylat    in Lösung gegangen.  Dann setzt man<B>160</B> Teile     Bariumhydroxyd     zu, verdampft das Wasser     und    zieht mit      Alkohol aus. Nach Vertreibung des     Lösun        s-          mittels        hinterbleibt    die neue Base, wie in  Beispiel<B>1,</B> in salbenartiger Form.  



  Die     Methylierung        hann    auch in Gegen  wart anderer geeigneter Lösungsmittel aus  geführt werden. Ferner lassen sich andere  reaktionsfähige     Methylester,    wie zum Bei  spiel     Methylnitrat,    andere     Methylha.logenide,     aromatische     Sulfosäuremethylester        usw.,    ver  wenden.



  Process for the preparation of a quaternary ammonium compound. It has been found that a quaternary ammonium compound can be obtained by adding oleyl-diethyl-ethylenediamine of the formula <B> C, CO. </B> NH. CH-, C1I2. <B> N </B> (CII-15) 2 is reacted with reactive ethyl esters and the base is liberated from the salts obtained by customary methods.



  The -Methyl-diethv1-olev <B> 1 </B> ja.m'doäthyl-ain- monium hydroxide is a thick, ointment-like mass that is easily soluble in water or <B> Al- </B> alcohol . The diluted aqueous solution has a strong alkaline reaction. With acids, the base gives neutral salts which are readily soluble in water and organic solvents, which in the anhydrous state also form ointment-like proportions. Both the free base and its salts have a strong foam capacity in an aqueous solution.



  The new compound should be used for technical purposes, for example as a wetting agent or as an additive to dye baths.



  <I>Example <B>1:</B> </I> <B> 380 </B> parts oleyl diethyl ethylenediamine are mixed with 142 parts iodomethyl. Conversion occurs with strong heat development. The resulting ointment is dissolved in water, the base is released by adding 150 parts of freshly precipitated superoxide and the solution freed from the silver salts is evaporated.

   The methyl-diethyl-olc - \, # lamido, # thvl- ammonium hydroxide is left as an ointment-like mass.



  Example 2: 380 parts of oleyl diethyl ethylenediamine are vigorously stirred with 126 parts of dimethyl sulfate and 4000 parts of water. After about an hour the reaction is over and the methyl-diethyl-oleylamidoethyl-ammonium-suliomethylate has gone into solution. Then <B> 160 </B> parts of barium hydroxide are added, the water is evaporated and extracted with alcohol. After the solvent has been driven off, the new base remains in an ointment-like form, as in Example <B> 1 </B>.



  The methylation can also be carried out in the presence of other suitable solvents. Other reactive methyl esters, such as methyl nitrate, other methyl halides, aromatic sulfonic acid methyl esters, etc., can also be used.

Claims (1)

PATENTANSPRUCH- Verfahren zu#7 Darstellung einer Am- moniumverbindung, dadurch gekennzeichnet, dass man Oleyl-diäthyl-äthylendiamin der Formel Cl-, <B>.</B> HI., <B>. Co .</B> NH <B>.</B> CH2. CH2. <B>N</B> (C, H') 2 mit reaktionsfähigen Methylestern umsetzt und aus den erhaltenen Salzen die Base in Freiheit setzt. PATENT CLAIM process for # 7 preparation of an ammonium compound, characterized in that oleyl diethyl ethylenediamine of the formula Cl-, <B>. </B> HI., <B>. Co. </B> NH <B>. </B> CH2. CH2. <B> N </B> (C, H ') 2 reacts with reactive methyl esters and sets the base free from the salts obtained. Das Methyl-diäthyl-oleyla.midoäthyl-am- moniumhydroxyd stellt eine dicke, salben- artige Masse dar, die in Wasser oder<B>Al-</B> kohol leicht löslich ist. Die verdünnte wäs serige Lösung reagiert stark alkalisch. Mit Säuren gibt die Base in Wasser und orga nischen Lösungsmitteln leicht lösliche, neu trale Salze, welche in wasserfreiem, Zu stande ebenfalls salbenartige Massen bilden. Sowohl die freie Base, wie ihre Salze be sitzen in wässeriger Lösung stark-es Schaum- im vermögen. Methyl-diethyl-oleyla.midoethyl-ammonium hydroxide is a thick, ointment-like mass that is easily soluble in water or <B> Al </B> alcohol. The diluted aqueous solution has a strong alkaline reaction. With acids, the base gives neutral salts which are easily soluble in water and organic solvents and which also form ointment-like masses in anhydrous state. Both the free base and its salts have a strong ability to foam in an aqueous solution. Die neue Verbindung soll zu technischen Zwecken, zum Beispiel als Benetzun 'cs- mittel oder als Zusatz zu Farbbädern, Ver wendung fiiiden. <B>UNTERANSPRUCH:</B> Verfahren nach Patentanspruch, dadurch gekennzeichnet" dass man die Metliylierung in Gegenwart von Lösungsmitteln ausführt. The new compound is intended to be used for technical purposes, for example as a wetting agent or as an additive to dye baths. SUBClaim: Process according to patent claim, characterized in that the methylation is carried out in the presence of solvents.
CH130881D 1927-07-26 1927-07-26 Process for the preparation of a quaternary ammonium compound. CH130881A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH130881T 1927-07-26

Publications (1)

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CH130881A true CH130881A (en) 1929-01-15

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CH130881D CH130881A (en) 1927-07-26 1927-07-26 Process for the preparation of a quaternary ammonium compound.

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CH (1) CH130881A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE879388C (en) * 1938-05-15 1953-06-11 Hoechst Ag Process for the preparation of quaternary ammonium salts
EP0327379A2 (en) * 1988-02-05 1989-08-09 CRODA INTERNATIONAL plc Humectants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE879388C (en) * 1938-05-15 1953-06-11 Hoechst Ag Process for the preparation of quaternary ammonium salts
EP0327379A2 (en) * 1988-02-05 1989-08-09 CRODA INTERNATIONAL plc Humectants
EP0327379A3 (en) * 1988-02-05 1991-01-09 CRODA INTERNATIONAL plc Humectants

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