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.[7]
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):[7]
CH3CH2CH2OH + O2 + NH3 → CH3CH2CN + 3 H2O
Propionitrile is a byproduct of the electrodimerisation of acrylonitrile to adiponitrile.
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.
The nitrile aldol reaction with benzophenone, followed by reduction of the nitrile with lithium aluminium hydride gives 2-MDP. This agent possesses appetite suppressant and antidepressant properties.
Safety
The toxicity LD50 of propionitrile is listed as 39 mg/kg[8] and as 230 my (both rats, oral).[7]
In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propionitrile by nickel-catalyzed hydrogenation of acrylonitrile.[9] This site is now one of the two Superfund cleanup sites in South Carolina.[9]
References
^ ab"Propionitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Identification. Retrieved 1 November 2013.
^CRC Handbook of Chemistry and Physics, 52nd Ed., p. D-153
^HSDB: Propionitrile, TOXNET, U.S. National Library of Medicine, retrieved 30 Oct 2015
^"propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012.