Glycolonitrile

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Glycolonitrile
Skeletal formula of glycolonitrile
Ball and stick model of glycolonitrile
Spacefill model of glycolonitrile
Names
IUPAC name
2-Hydroxyacetonitrile[2]
Other names
Identifiers
605328
107-16-4 YesY
ChemSpider 7569 N
EC number 203-469-1
Jmol-3D images Image
MeSH glycolonitrile
PubChem 7857
Properties
C2H3NO
Molar mass 57.05 g·mol−1
Appearance Colourless, oily liquid
Odor odorless[3]
Density 1.10 g/mL (18.89°C)[3]
Melting point < −72 °C; −98 °F; 201 K [3]
Boiling point 99.6 °C; 211.2 °F; 372.7 K at 2.3 kPa
soluble[3]
Vapor pressure 1 mmHg (62.78°C)[3]
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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.[4] It is a colourless liquid that dissolves in water and ether. Because glycolonitrile decomposes readily into formaldehyde and hydrogen cyanide, it is listed as an extremely hazardous substance.

Synthesis and reactions[edit]

Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide under acidic conditions. This reaction is catalysed by base.[5] Gylcolonitrile 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.[5]

References[edit]

  1. ^ a b c d "Glycolonitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Retrieved 8 November 2013. 
  2. ^ "glycolonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 5 June 2012. 
  3. ^ a b c d e f g h i "NIOSH Pocket Guide to Chemical Hazards #0304". National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ Gaudry, R. (1955). "Glycolonitrile". Org. Synth. ; Coll. Vol. 3, p. 436 
  5. ^ a b Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363