Carbohydrazide

Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It is a white, water-soluble solid.[1][2] It decomposes upon melting.[2] 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.

Carbohydrazide
Names
IUPAC name
1,3-Diaminourea
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.126
UNII
Properties
CH6N4O
Molar mass 90.09 g/mol
Density 1.341 g/cm3
Melting point 153 to 154 °C (307 to 309 °F; 426 to 427 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Production

Industrially the compound is produced by treatment of urea with hydrazine:[3]

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.[2] 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.[4]

Industrial uses
  • Oxygen scrubber: carbohydrazide is used to remove oxygen in boiler systems. Oxygen scrubbers prevent corrosion.[5][6]
  • Precursor to polymers: carbohydrazide can be used as a curing agent for epoxide-type resins.[2]
  • 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.[2]
  • Carbohydrazide has been used to develop ammunition propellants,[7] stabilize soaps,[2] 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.[8]

References
  1. Inorganic Syntheses Volume IV. McGraw-Hill Book Company, Inc. 1953. p. 35. ISBN 9780470132678.
  2. Kurzer, Frederick; Michael Wilkinson (February 1970). "Chemistry of carbohydrazide and thiocarbohydrazide". Chemical Reviews. 70: 111–149. doi:10.1021/cr60263a004.
  3. Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a13_177.
  4. 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. doi:10.1107/S0567740879003575
  5. Buecker, Brad (1997). Power Plant Water Chemistry A Practical Guide. PennWell Publishing Company. pp. 13–16. ISBN 978-0-87814-619-2.
  6. "Patent US4269717". Retrieved 8 October 2012.
  7. "Patent US2970899". Retrieved 8 October 2012.
  8. "MSDS". Retrieved 8 October 2012.
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