Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde.
Synthesis and reactions
Glycolonitrile is produced by reacting
formaldehyde with
hydrogen cyanide at near-neutral pH, but with small amounts of catalytic base.
[Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. ] Glycolonitrile polymerizes under alkaline conditions above pH 7.0. As the product of polymerization is an amine with a basic character, the reaction is self-catalysed, gaining in speed with ongoing conversion.
Glycolonitrile can react with ammonia to give aminoacetonitrile, which can be hydrolysed to give glycine:
- HOCH2CN + NH3 → H2NCH2CN + H2O
- H2NCH2CN + 2 H2O → H2NCH2CO2H + NH3
The industrially important
chelating agent EDTA is prepared from glycolonitrile and
ethylenediamine followed by hydrolysis of the resulting tetranitrile. Nitrilotriacetic acid is prepared similarly.
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