Destructive Oxidation of Mirex

Abstract

The perchlorinated aliphatic substance Mirex (perchloropentacyclo[5.3.0.0 ^2,6.0 ^3,9.0 ^4,8]decane) once had widespread use as an insecticide and still has limited application as a termiticide. Mirex resists direct oxidation by ruthenium tetraoxide. It undergoes a six-electron reduction in acetonitrile at –1·2 V from the Ag/AgCl reference potential. One or more chlorines are readily substituted by methoxide at 90°C. Both the reduced and the methoxylated derivatives are oxidized at room temperature by alkaline hypochlorite or persulfate in the presence of a homogeneous ruthenium catalyst. Only a trace amount of cyclohexane-extractable residue remains, but not all of the chlorine is released as ionic chloride. This implies that the oxidation products include some unidentified water-soluble organochlorine substances.