Oxamide
Chemical compound
Oxamide is the organic compound with the formula (CONH2)2. This white crystalline solid is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Oxamide is the diamide derived from oxalic acid, and the hydrate of cyanogen.
01Preparation
Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.
It can also be prepared from formamide by glow-discharge electrolysis.
It can also be prepared from ammonium oxalate via pyrolysis.
02Application
The main application is as a substitute for urea in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea.
It is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP rocket motors as a high performance burn rate suppressant. The use of oxamide in concentrations of 1-3 wt% has shown to slow the linear burn rate while having minimal impact on propellant specific impulse.
N,N'-substituted oxamides are supporting ligands for the copper-catalyzed amination and amidation of aryl halides in Ullmann-Goldberg reaction, including relatively unreactive aryl chloride substrates.
03Reactions
It dehydrates above 350 °C releasing cyanogen. Oxamide derivatives form self-assembled monolayers consisting of a hydrogen bonded network.
Sources and credits
This article is adapted from the Wikipedia article “Oxamide”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Oxalamide 200.svg by Emeldir (talk), Public domain
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