CH104101A - Process for the preparation of diallylcyanamide. - Google Patents

Process for the preparation of diallylcyanamide.

Info

Publication number
CH104101A
CH104101A CH104101DA CH104101A CH 104101 A CH104101 A CH 104101A CH 104101D A CH104101D A CH 104101DA CH 104101 A CH104101 A CH 104101A
Authority
CH
Switzerland
Prior art keywords
diallylcyanamide
cyanamide
preparation
allyl
water
Prior art date
Application number
Other languages
German (de)
Inventor
Hermann Prof Dr Staudinger
Original Assignee
Hermann Prof Dr Staudinger
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 Hermann Prof Dr Staudinger filed Critical Hermann Prof Dr Staudinger
Publication of CH104101A publication Critical patent/CH104101A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/04—Cyanamides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren zur Darstellung von     Diallyleyanamid.       Es ist bekannt, dass man zu     Dialkyl-    oder       Diarylcyanamiden    gelangen kann, indem  man     Cyanamidnatrium        bezw.        Cyanamid-          caleium    in alkoholischer Lösung mit Ha  logenalkylen umsetzt. Der Versuch, dieses  Verfahren auf die Gewinnung des     Diallyl-          cyanamids    zu übertragen, schlug fehl.  



  Hingegen wurde überraschenderweise ge  funden, dass man diese bisher unbekannte       Verbindung    in glatter Weise gewinnen  kann, indem man     Allylhaloide    auf     Cyana-          midsalze    bei Gegenwart von Wasser zur Um  setzung bringt.  



  Die Reaktion kann bei     gewöhnlicher    oder  schwach erhöhter Temperatur vorgenommen  werden.  



  Die entsprechenden     gesättigten    Derivate  des     Cyanamids,    wie zum Beispiel das     Di-          propylcy        anamid,    lassen sich unter diesen       Bedingungen.    entweder gar nicht oder nur  in sehr. unbefriedigender Ausbeute ge  winnen.  



  Das     Diallylcyanamid    stellt eine farblose  Flüssigkeit dar, welche unter 9 mm Druck  bei 95   schmilzt.    <I>Beispiel:</I>  Eine Lösung von 100     gr        Natrium-          cyanamid    (1     Mol.,    83 % Salz) in 200 cm'  Wasser wird mit 342     gr        Allylbromid    (2       Mol.)    48     Stunden    geschüttelt oder     turbi-          niert,    und zwar zweckmässig unter anfäng  licher Kühlung.

   Nach dieser Zeit wird das  aufschwimmende Öl abgehoben und der  fraktionierten Destillation im Vakuum un  terworfen, wobei das     Diallylcyanamid    in  einer Ausbeute von 85 % erhalten wird.  



  Bei Anwendung von     Allylchlorid    muss  man, um rasche Umsetzung zu erreichen,  auf 40' erwärmen.



  Process for the preparation of diallyleyanamide. It is known that dialkyl or diaryl cyanamides can be obtained by using cyanamide sodium or. Cyanamid- caleium in alcoholic solution with haloalkylenes. The attempt to transfer this process to the production of diallyl cyanamide failed.



  In contrast, it was surprisingly found that this hitherto unknown compound can be obtained smoothly by converting allyl haloids to cyanamide salts in the presence of water.



  The reaction can be carried out at ordinary or slightly elevated temperature.



  The corresponding saturated derivatives of cyanamide, such as, for example, propylcyanamide, can be converted under these conditions. either not at all or only to a great extent. win an unsatisfactory yield.



  The diallylcyanamide is a colorless liquid which melts at 95 under 9 mm pressure. <I> Example: </I> A solution of 100 g sodium cyanamide (1 mol., 83% salt) in 200 cm 'of water is shaken or turbinated with 342 g allyl bromide (2 mol.) For 48 hours, and although expedient with initial cooling.

   After this time, the floating oil is lifted off and subjected to fractional distillation in vacuo, the diallylcyanamide being obtained in a yield of 85%.



  When using allyl chloride you have to warm to 40 'in order to achieve rapid conversion.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Diallyl- cyanamid, dadurch gekennzeichnet, dass man Allylhaloide mit Cyanamidsalzen in Gegen wart von Wasser zur Umsetzung bringt. Das Diallylcyanamid stellt eine farblose Flüssigkeit dar, welche unter 9 mm Druck bei 95 schmilzt. PATENT CLAIM: Process for the preparation of diallyl cyanamide, characterized in that allyl haloids are reacted with cyanamide salts in the presence of water. The diallylcyanamide is a colorless liquid which melts at 95 under 9 mm pressure.
CH104101D 1923-04-09 1923-04-09 Process for the preparation of diallylcyanamide. CH104101A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH104101T 1923-04-09

Publications (1)

Publication Number Publication Date
CH104101A true CH104101A (en) 1924-05-01

Family

ID=4362920

Family Applications (1)

Application Number Title Priority Date Filing Date
CH104101D CH104101A (en) 1923-04-09 1923-04-09 Process for the preparation of diallylcyanamide.

Country Status (1)

Country Link
CH (1) CH104101A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2858338A (en) * 1954-12-30 1958-10-28 Monsanto Chemicals Preparation of unsaturated cyanamides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2858338A (en) * 1954-12-30 1958-10-28 Monsanto Chemicals Preparation of unsaturated cyanamides

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