The identification of highly chlorinated ethers and diethers in river sediment near an epichlorohydrin plant

In harbour sediment samples taken near an epichlorohydrin production plant, a series of highly chlorinated ethers and diethers were detected viz. three isomeric bis(dichloropropyl)ethers, several structurally closely related ethers with 9 carbon atoms (C₉ ethers), a number of C₁₂ ethers and diethers, and finally several C₁₅ ethers. The formation of this new class of ether compounds can be explained on the basis of the chemistry of the addition of HOCl to allylchloride. After initial addition of Cl⁻, a reactive intermediate is formed which may react with the product dichloropropanol, to give the C₆ ethers, or may polymerize with the starting compound allylchloride followed by reaction with the product, to give the C₉, C₁₂ and C₁₅ ethers.