Oxamide

Structural formula
General
Surname	Oxamide
other names	Ethanediamide Ethanedioic acid amide Oxalamide Oxalic acid diamide
Molecular formula	C 2 H 4 N 2 O 2
Brief description	colorless needles
External identifiers / databases
CAS number 471-46-5 EC number 207-442-5 ECHA InfoCard 100.006.767 PubChem 10113 Wikidata Q423341
properties
Molar mass	88.07 g · mol -1
Physical state	firmly
Melting point	350 ° C (decomposition)
solubility	hardly soluble in water and in ethanol , insoluble in diethyl ether
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-315-319 P: 305 + 351 + 338
Thermodynamic properties
ΔH f 0	−504.4 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxamide , also called oxalic acid diamide , is the diamide of oxalic acid .

The high melting point can be explained by strong hydrogen bonds in the solid.

Manufacturing

Oxamid can be made in the following ways:

• Hydrolysis of dicyan
• partial oxidation of hydrogen cyanide with
  • Oxygen in the presence of copper (II) nitrate (Hoechst) or
  • Hydrogen peroxide

${\displaystyle \mathrm {HCN\ +\ H_{2}O_{2}\longrightarrow \ (CONH_{2})_{2}} }$

• Ammonolysis of di alkyl oxalates (by Ube )

use

• Fertilizer substitute for urea , as it only gradually releases nitrogen due to its poor solubility in water and slow hydrolysis (main application)
• Stabilizer in cellulose nitrate (gun cotton)
• Moderator in the combustion in rocket engines with ammonium perchlorate mixtures

Individual evidence

1. ↑ ^{a b c} J. Falbe, M. Regitz (Ed.): Römpp Lexikon Chemie . 10th edition, Thieme, Stuttgart a. New York, 1996-1999. P. 3062.
2. ↑ ^{a b} data sheet Oxamide purum from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-22.
4. ↑ Sheridan, RC, Brown, EH; Preparation of Oxamide from Hydrogen Cyanide and Hydrogen Peroxide , J. Org. Chem, 1965, 30 (2), 669-670