1,4-Dioxane
chemical compound
1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered.
1,4-Dioxane is miscible in water, essentially nonvolatile when dissolved in water, not well adsorbed by activated carbon, and not readily oxidized by common oxidants.
Dioxane is used as a solvent in manufacturing applications, and as a stabilizer for the transport of chlorinated hydrocarbons in aluminium containers. It is a highly flammable substance that produces toxic vapors when heated.
Although it is a trace material in commonly used products, such as cosmetics, dioxane is considered a hazardous contaminant and potential carcinogen in many countries, requiring government monitoring of amounts used in manufacturing and its presence in air, drinking water, and ecosystems.
History and synthesis
The compound was discovered by Portuguese professor Agostinho Vicente Lourenço in 1860 by a reaction of diethylene glycol with 1,2-dibromoethane. He initially designated it ether of glycol and correctly identified its empirical formula, but measured its boiling point at about 95 °C. Three years later C. A. Wurtz obtained it by another method, called it dioxyethylene and studied some of its chemical properties.
Dioxane is industrially produced since the 1920s by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide.
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