An abundant chlorinated furanone in the spent chlorination liquor from pulp bleaching

Gas chromatography with electron capture detection of acetylated spent liquors from the bleaching of chemical pulp showed a large peak attributed to an unknown compound. The same peak was present in the analysis of chlorinated naturally occurring humic acid. GC multistage mass spectrometry, proton nmr, carbon-13 nmr, UV and IR spectroscopy showed the compound to be 3,4-dichloro-5-(dichloromethyl)-5-hydroxy-2-furanone. The unacetylated furanone exhibited weak mutagenic activity in the Ames test using Salmonella typhimurium TA100. It also showed a slightly elevated propensity to bioaccumulation and was chemically unstable.