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Carbohydrazide

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Formula
  
CH6N4O

Density
  
1.34 g/cm³

Molar mass
  
90.09 g/mol

Carbohydrazide httpsuploadwikimediaorgwikipediacommons44

Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It is a white, water-soluble solid. It decomposes upon melting. A number of carbazides are known where one or more N-H groups are replaced by other substituents. They occur widely in the drugs, herbicides, plant growth regulators, and dyestuffs.

Contents

Production

Industrially the compound is produced by treatment of urea with hydrazine:

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 carbonate esters. It can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N2H5]Cl 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.

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: carbohyrazide 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.
  • Carbohydrazide has been used to develop ammunition propellants, stabilize soaps, and used a reagent in organic synthesis.

    • 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.

    References

    Carbohydrazide Wikipedia
    (Text) CC BY-SA


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