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.[3] 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. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, in outer space.[4]
| |||
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Hydroxyacetonitrile | |||
Other names
| |||
| Identifiers | |||
3D model (JSmol)
|
|||
| 605328 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.155 | ||
| EC Number |
| ||
| MeSH | glycolonitrile | ||
PubChem CID
|
|||
| UNII | |||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
| Properties | |||
| C2H3NO | |||
| Molar mass | 57.052 g·mol−1 | ||
| Appearance | Colourless, oily liquid | ||
| Odor | odorless[2] | ||
| Density | 1.10 g/mL (18.89°C)[2] | ||
| Melting point | < −72 °C; −98 °F; 201 K[2] | ||
| Boiling point | 99.6 °C; 211.2 °F; 372.7 K at 2.3 kPa | ||
| soluble[2] | |||
| Vapor pressure | 1 mmHg (62.78°C)[2] | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
|
forms cyanide in the body[2] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
|
none[2] | ||
REL (Recommended)
|
C 2 ppm (5 mg/m3) [15-minute][2] | ||
IDLH (Immediate danger)
|
N.D.[2] | ||
| 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).
| |||
Synthesis and reactions
editGlycolonitrile is produced by reacting formaldehyde with hydrogen cyanide at near-neutral pH, but with small amounts of catalytic base.[5] 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.[5]
References
edit- ^ 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.
- ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0304". National Institute for Occupational Safety and Health (NIOSH).
- ^ Gaudry, R. (1955). "Glycolonitrile". Organic Syntheses; Collected Volumes, vol. 3, p. 436.
- ^ Queen Mary University of London (23 January 2019). "Astronomers find star material could be building block of life". EurekAlert!. Retrieved 24 January 2019.
- ^ 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