Oxamide

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Oxamide
Oxamide
Oxamide
Names
IUPAC name
Ethanediamide
Other names
Oxamide
Oxalamide
Oxamimidic acid
Diaminoglyoxal
Oxalic acid diamide
1-Carbamoyl-formimidic acid
Identifiers
471-46-5 YesY
ChEBI CHEBI:48248 N
ChemSpider 9709 N
EC number 207-442-5
Jmol-3D images Image
PubChem 10113
Properties
C2H4N2O2
Molar mass 88.0654 g/mol
Appearance White powder
Density 1.667 g/cm3
Soluble
Solubility ethanol
Hazards
EU classification Mild Irritant (6.1)
R-phrases R36
S-phrases S25
Flash point >300 °C
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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[edit]

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

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.

Reactions[edit]

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

References[edit]

  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[edit]