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2-Phenoxyethanol, known early on as ethylene glycol monophenyl ether, is a high-boiling, oily liquid that is moderately water-soluble. It has a long history and several uses in chemical manufacturing and consumer products.
The earliest mention of 2-phenoxyethanol in the chemical literature appeared in 1894, when Ernst Roithner at the University of Vienna published a treatise on ethylene oxide. In the article, Roithner described the synthesis of 2-phenoxyethanol via the reaction of ethylene oxide with phenol in a basic medium.
Two years later, in a paper about γ-phenoxy derivatives of malonic and acetic acids and the compounds used to synthesize them, William Henry Bentley, Edward Haworth, and William Henry Perkin, Jr.,* at Owens College (Manchester, UK) reported the preparation of 2-phenoxyethanol from sodium phenolate and ethylene chlorohydrin (2-chloroethanol). In 1919, R. E. Rindfusz at the University of Illinois (Urbana–Champaign) used this method to make 2-phenoxyethanol in the course of synthesizing chromanes (dihydrobenzopyrans) and coumaranes (dihydrobenzofurans). A refined version of Perkin et al.’s synthesis is used to manufacture 2-hydroxyethanol today.
2-Phenoxyethanol has many industrial uses—primarily as a solvent for dyes, inks, and resins; a lubricant preservative; and a reagent in organic chemical synthesis. In consumer products, its uses range from a preservative for cosmetics and drugs to a fixative for perfumes to an attractant in insecticides. In one ironic instance, it is a component of a hair formulation that claims to be “preservative-free”.
References to 2-phenoxyethanol often omit the numerical prefix, but this is ambiguous because of the existence of an isomer, 1-phenoxyethanol1. The isomer appears much less frequently in the chemical literature and has far fewer commercial uses.
1. CAS Reg. No. 56101-99-6.
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