Abstract
Abstract2‐Chloropropenal (2‐chloroacrolein), a constituent of softwood kraft chlorination effluent that gives strongly positive results in the Salmonella mutagenicity assay (Ames Test), was reacted with various nucleophiles and the resulting effect on mutagenicity monitored. Nucleophiles such as hydroxide ion and sulfur dioxide (HSO−3, SO3) proved very effective in reducing the mutagenicity of aqueous 2‐chloropropenal solutions. The application of other strong nucleophiles, (glutathione, pyrrolidine and sodium thiosulfate) to 2‐chloropropenal also produced substantial benefits in terms of mutagenicity reduction. Further experimentation revealed that the loss of mutagenicity was not the result of the removal of organically bound chlorine but rather the removal of the ethylenic group in 2‐chloropropenal, possibly as a consequence of undergoing Michael‐type 1,4‐addition reactions with the various nucleophiles. In the treatment of 2‐chloropropenal with alkali (pH 9), additional condensation of the acrolein derivative to a polymer was demonstrated by gel permeation chromatography.
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