Carbohydrazide
Chemical compound
From Wikipedia, the free encyclopedia
Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It appears as a white solid that is soluble in water,[1][2] but not in many organic solvents, such as ethanol, ether or benzene. 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.
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| Names | |
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| IUPAC name
1,3-Diaminourea | |
| Other names
Carbohydrazine | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.126 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| CH6N4O | |
| Molar mass | 90.09 g/mol |
| Density | 1.341 g/cm3 |
| Melting point | 153–154 °C (307–309 °F; 426–427 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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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: 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.[2]
- 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.[citation needed]
- Carbohydrazide has been used to develop ammunition propellants,[7] stabilize soaps,[2] and is used as a reagent in organic synthesis.
- Salts of carbohydrazide, such as nitrate, dinitrate and perchlorate, can be used as secondary explosives.[8] Complex salts of carbohydrazide, like bis(carbohydrazide)diperchloratocopper(II) and tris(carbohydrazide)nickel(II) perchlorate, can be used as primary explosives in laser detonators.[9]
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.[10]