Glycolonitrile

Glycolonitrile, also known as hydroxyacetonitrile or formaldehyde cyanohydrin, is an organic compound with the formula HOCH2CN[1]. It is the simplest cyanohydrin and is derived from formaldehyde. Glycolonitrile is a colorless liquid that dissolves in water and ether. However, it is listed as an extremely hazardous substance due to its tendency to decompose readily into formaldehyde and hydrogen cyanide[1].

Synthesis and Reactions

Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide at near-neutral pH, with small amounts of catalytic base[1]. It polymerizes under alkaline conditions above pH 7.0, and the product of polymerization is an amine with a basic character, making the reaction self-catalyzed[1]. Glycolonitrile can react with ammonia to give aminoacetonitrile, which can be hydrolyzed to give glycine[1].

Uses and Hazards

Glycolonitrile is used as a solvent, barrier resin additive, organic intermediate in the synthesis of bactericides and fungicides, and in pharmaceutical production[2]. However, it poses significant hazards due to its combustible nature and the production of poisonous gases, including cyanides, when involved in a fire[2]. Exposure to glycolonitrile can cause fatal cyanide poisoning, with symptoms including flushing of the face, chest tightness, nausea and vomiting, weakness, lightheadedness, confusion, headache, dizziness, and trouble breathing[2]. Higher exposures can lead to convulsions, irregular heartbeat, coma, and death[2]. Repeated exposure may cause personality changes such as depression, anxiety, or irritability, and glycolonitrile may damage the nervous system[2].

Safety Precautions

To handle glycolonitrile safely, it is essential to prevent skin contact and eye contact[2][3]. In case of skin contact, immediate washing or showering is necessary to remove the chemical[2]. Emergency shower facilities and eye wash fountains should be provided in the immediate work area[2]. If glycolonitrile is spilled or leaked, the area should be evacuated, ignition sources removed, and the spill absorbed with a material like vermiculite or dry sand before disposal as hazardous waste[2].

Detection in Outer Space

In January 2019, astronomers reported the detection of glycolonitrile in outer space, suggesting it as a possible building block of life among other such molecules[1].

Citations:

[1] https://en.wikipedia.org/wiki/Glycolonitrile

[2] https://nj.gov/health/eoh/rtkweb/documents/fs/0962.pdf

[3] https://www.cdc.gov/niosh/npg/npgd0304.html

[4] https://pubchem.ncbi.nlm.nih.gov/compound/Glycolonitrile

[5] https://www.sigmaaldrich.com/US/en/product/aldrich/374768