Reports that bis(chloromethyl) ether (BCME) is carcinogenic have prompted numerous investigations into the formation and decomposition of the compound. In this study, it is shown that the compound forms rapidly in a chloromethylating medium (HC1-HCHO-ZnC12) at low levels (100 ppm) and attains a fairly steady concentration of 300-500 ppm. Methods for destroying BCME are discussed including the rates of destruction in homogeneous and heterogeneous media. Although BCME is considered reactive, it is not readily decomposed by water or aqueous base because of its low solubility. In homogeneous media such as MeOH-H2O. the rate of hydrolysis is much faster. The reaction of BCME with aqueous ammonia is very fast and a reaction path to hexamethylenetetramine is suggested. Gaseous BCME reacts rapidly with aqueous systems, particularly alkaline solutions, due to greater contact efficiency.
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