Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It appears as a white solid that is soluble in water,
Production
Industrially the compound is produced by treatment of
urea with
hydrazine:
[Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. .]
- OC(NH2)2 + 2 N2H4 → OC(N2H3)2 + 2 NH3
It can also be prepared by reactions of other C1-precursors with
hydrazine, such as
.
It can be prepared from
phosgene, but this route cogenerates the
hydrazinium salt N
2H
5Cl and results in some diformylation. Carbazic acid is also a suitable precursor:
- N2NH3CO2H + N2H4 → OC(N2H3)2 + H2O
Structure
The molecule is nonplanar. All nitrogen centers are at least somewhat pyramidal, indicative of weaker C-N pi-bonding. The C-N and C-O distances are about 1.36 and 1.25 Å, respectively.
[Ottersen, T.; Hope, H. "The Structure and Electron Deformation Density Distribution of Carbonohydrazide (Carbohydrazide) at 85 K" Acta Crystallographica B 1979, volume 35, p373-p378. ]
Industrial uses
-
Oxygen scrubber: carbohydrazide is used to remove oxygen in boiler systems. Oxygen scrubbers prevent corrosion.
-
Precursor to polymers: carbohydrazide can be used as a curing agent for epoxide-type resins.
-
Photography: carbohydrazide is used in the silver halide diffusion process as one of the toners. Carbohydrazide is used to stabilize color developers that produce images of the azo-methine and azine classes.
-
Jet fuel: carbohydrazine can be used as a component in jet fuels, as a large amount of heat is being produced when the material is burned.
-
Carbohydrazide has been used to develop ammunition propellants,
-
Salts of carbohydrazide, such as nitrate, dinitrate and perchlorate, can be used as secondary explosives.
Hazards
Heating carbohydrazide may result in an explosion. Carbohydrazide is harmful if swallowed, irritating to eyes, respiratory system, and skin. Carbohydrazide is toxic to aquatic organisms.
