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 1H and 13C 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 μg/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. The principal factor determining their formation appears to be the high concentration of monoterpenes remaining in the P. radiata brown stock produced in the mill's continuous digester. © 1990, American Chemical Society. All rights reserved.