Oxamide

Oxamide
IUPAC name Ethanediamide
Other names Oxamide Oxalamide Oxamimidic acid Diaminoglyoxal Oxalic acid diamide 1-Carbamoyl-formimidic acid
Identifiers
CAS number	471-46-5
Properties
Molecular formula	C2H4N2O2
Molar mass	88.0654 g/mol
Appearance	White powder
Density	1.667 g/cm3
Solubility in water	Soluble
Solubility	ethanol
Hazards
EU classification	Mild Irritant (6.1)
R-phrases	R36
S-phrases	S25
Flash point	>300 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Production and applications

Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.^[1]

The main application is as substitute 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.

Reactions

Upon heating above 350 °C, it decomposes to cyanogen and water. Oxamide forms self-assembled monolayers consisting of a hydrogen bonded network.^[2]

References

1. ^ Wilhelm Riemenschneider, Minoru Tanifuji "Oxalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a18_247.
2. ^ Nguyen T.L., Fowler F.W., Lauher J.W., "Commensurate and incommensurate hydrogen bonds. An exercise in crystal engineering." Journal of the American Chemical Society, 123(44), pp. 11057-64, 2001. doi:10.1021/ja016635v

External links

• Oxamide