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.
Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.
Prepd from formamide by glow-discharge electrolysis: Brown et al.
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.
Upon heating above 350 °C, it decomposes to cyanogen and water. Oxamide derivatives form self-assembled monolayers consisting of a hydrogen bonded network.
[musick - Matt Harvey; lyrixxx - Ross Sewage, 1996]
Fastened down and secured to the operating table, With scalpels and cutlery I
will work upon your aesthetics, A most afflictive process you are made to
endure, Without the solacing service of a general anasthetic... Forcibly
penetrating the palpebra, I gouge and cut into the ciliary body, Severing the
nerve, your eye is knocked from its orbit, As you can plainly see...
Dissatisfied with your over all being, I formulate a plan of operation, A
large incision into the abdomen is made, To perform general enucleation... I
give you an apendectomy, Removing organs unnecessary, A spare kidney is
excised, In pain you writhe... (chorus) I slice the renal artery,
Gastro-intestinal-otomy, Digestive tract dislocation, Subjected to
enucleation... With monocular vision you can now regard, The constituents of
your gut I have displaced, Depurating the shell, your thorax beautifully
carved, Your abdomen now a barren landscape... Fracturing the rib cage with a
raspatory, As your gullet is gorged with sanguineous muco-sputter, Not yet
complete curtailing your anatomy, I delve to the heart of the matter...
Exhuming your entrails, Discarded organs grow stale, Severing the ventricle,