Glycolonitrile

Glycolonitrile
Names
IUPAC name
2-Hydroxyacetonitrile[1]
Other names
  • Cyanomethanol[2]
  • Formaldehyde cyanohydrin[2]
  • Glycolic nitrile[2]
  • Hydroxyacetonitrile[2]
  • Hydroxymethylnitrile
Identifiers
107-16-4 YesY
3D model (Jmol) Interactive image
605328
ChemSpider 7569 N
ECHA InfoCard 100.003.155
EC Number 203-469-1
MeSH glycolonitrile
PubChem 7857
UNII ZCI474BE63 N
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]
Hazards
Main hazards forms cyanide in the body[3]
US health exposure limits (NIOSH):
PEL (Permissible)
none[3]
REL (Recommended)
C 2 ppm (5 mg/m3) [15-minute][3]
IDLH (Immediate danger)
N.D.[3]
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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

  1. "glycolonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 5 June 2012.
  2. 1 2 3 4 "Glycolonitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Retrieved 8 November 2013.
  3. 1 2 3 4 5 6 7 8 9 "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. 1 2 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
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