Glycolonitrile

Glycolonitrile
Glycolonitrile
IUPAC name
2-Hydroxyacetonitrile
Other names
Formaldehyde cyanohydrin; Hydroxyacetonitrile; Glycolic nitrile; Cyanomethanol; Hydroxymethylnitrile
Identifiers
CAS number 107-16-4 YesY
PubChem 7857
Jmol-3D images Image 1
Properties
Molecular formula C2H3NO
Molar mass 57.05 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1] Because glycolonitrile decomposes readily into formaldehye and hydrogen cyanide, it is listed as an extremely hazardous substance.

Contents

Synthesis

Glycolonitrile can be synthesized by reacting formaldehyde with hydrogen cyanide under acidic conditions. This reaction takes place spontaneously even under aqueous conditions.[2]

Properties

Chemical properties

Gylcolonitrile polymerizes under alkaline conditions above pH 7.0. Arrhenius et al. have proposed the following mechanism for polymerization:[2]

Glycolonitrile polymerisation.gif

As the product of polymerization is an amine with a basic character, the reaction is self-catalysed, gaining in speed with ongoing conversion.

References

  1. ^ Gaudry, R. (1955), "Glycolonitrile", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0436 ; Coll. Vol. 3: 436 
  2. ^ a b Arrhenius et al., J. Org. Chem. 1997, 62, 5522-5525


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