Appearance Colourless liquid Formula C3H5N Molar mass 55.08 g/mol | Related compounds Density 792 kg/m³ | |
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Related alkanenitriles | ||
Propionitrile
Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.
Contents
Propionitrile meaning
Production
The main industrial route to this nitrile is the hydrogenation of acrylonitrile. It is also prepared by the ammoxidation of propanol (propionaldehyde can also be used instead):
CH3CH2CH2OH + O2 + NH3 → CH3CH2CN + 3 H2OPropionitrile is a byproduct of the electrodimerisation of acrylonitrile to adiponitrile.
In the laboratory propanenitrile can also be produced by the dehydration of propionamide, by catalytic reduction of acrylonitrile, or by distilling ethyl sulfate and potassium cyanide.
Applications
Propionitrile is a solvent similar to acetonitrile but with a slightly higher boiling point. It is a precursor to propylamines by hydrogenation. It is a C-3 building block in the preparation of the drug flopropione by the Houben-Hoesch reaction.
Safety
Propanenitrile is poisonous but weakly with an LD50 of 230 mg/kg (rats, oral). Propanenitrile has been determined to be teratogenic due to the metabolic release of cyanide.
In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propanenitrile by nickel-catalyzed reduction of acrylonitrile. This site is now one of the two Superfund cleanup sites in South Carolina.