epichlorohydrinactivated

Epichlorohydrin, formally known as 1-chloro-2,3-epoxypropane, is a chlorinated organic compound that features a strained three-membered epoxide ring adjacent to a chlorine substituent. Its molecular formula is C3H5ClO. It is a colorless to pale yellow liquid with a sharp odor, and its reactivity stems from the combination of the epoxide ring and the nearby chlorine atom, which makes it a versatile electrophile in downstream syntheses.

Industrial production typically relies on the chlorohydrin route. Allyl chloride reacts with chlorine and water to form glycidyl chloride, which is then treated with sodium hydroxide to induce intramolecular cyclization and yield epichlorohydrin. In practice, the process is conducted at scale in the chemical industry to provide a steady supply of this important intermediate. Alternative routes exist, including from glycerol derivatives, but the chlorohydrin pathway remains dominant for large-scale production.

The principal use of epichlorohydrin is as a monomer and chemical intermediate for epoxy resins. It reacts with phenols and bisphenol A to produce glycidyl ether resins, which cure to form durable thermosets. It also serves as a precursor to polyether polyols, various epoxy-functional materials, surfactants, and plasticizers. Its flexibility as a building block underpins many coatings, adhesives, and composite products.

Safety and handling considerations are significant. Epichlorohydrin is highly reactive and acts as a potent lachrymator; it is toxic by inhalation and skin contact and is considered a probable human carcinogen by some regulatory agencies. Handling requires adequate ventilation, appropriate protective equipment, and measures to prevent polymerization. It should be stored in tightly sealed containers away from heat and moisture. Disposal follows strict hazardous-waste regulations.