Glycidol

Glycidol is an epoxide and an alcohol, and as such is a highly reactive compound. It is miscible with water but also reacts with it. It decomposes when distilled at atmospheric pressure.

In 1909, chemist Nikolai Prilezhaev at the Warsaw University of Technology prepared glycidol by epoxidizing allyl alcohol with peroxybenzoic acid. This reaction was a breakthrough at the time and became known as the Prilezhaev oxidation. Glycidol is still manufactured in much the same way; but in 2018, a group of companies built a pilot plant in Teesside, UK, to make it via a “green” process.

Glycidol has a chiral center, but it is generally produced and used as the racemic mixture. It is used as a chemical intermediate and in the production of detergents, healthcare products, and industrial paints and coatings.

As shown in the hazard information table, glycidol presents an unusually large number of health risks. These factors were recently acknowledged when the US Food and Drug administration identified 19 substances as potentially harmful constituents of nicotine delivery systems (“e-cigarettes” and “e-liquids”). Glycidol, along with former Molecules of the Week diacetyl and ethylene glycol, is prominent in the FDA list. The agency now requires manufacturers and importers of the delivery systems to report the concentrations of each compound in its products.