Identification of novel chlorinated monoterpenes formed during kraft pulp bleaching of Pinus radiata

The chlorination stage bleaching effluents of a New Zealand kraft pulp and paper mill processing the softwood Pinus radiata contained a group of novel chlorinated monoterpenes. Fourteen compounds were isolated from the effluents by a combination of liquid-liquid extraction, column chromatography, and preparative gas chromatography. Mass spectral and super(1)H and super(13)C NMR data showed these compounds to be chlorinated and/or hydroxylated derivatives of P. radiata monoterpenes. The major compounds were a dichlorobornane and four dichloro-p-menthane-1,8-diols. The chlorinated monoterpenes were detected in total concentrations of 1400-12,300 mu g/L (70-600 g/air-dried tonne (ADT) bleached pulp) and they were the major class of low molecular weight extractable organic compounds present in the chlorination stage effluent.