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
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2858338A (en) * | 1954-12-30 | 1958-10-28 | Monsanto Chemicals | Preparation of unsaturated cyanamides |
-
1923
- 1923-04-09 CH CH104101D patent/CH104101A/en unknown
Cited By (1)
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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