Properties of some chlorinated polycyclic aromatic hydrocarbons with respect to chemical analysis

Abstract: This thesis describes chemical and biological properties of chloro-added and chloro-substituted PAHs with respect to chemical analysis. The work includes biological testing with Ames assay, study of chemical reactivities in chlorination reactions and retention characteristics on normal phase stationary phases for HPLC, as well as analysis of urban air samples with respect to chlorinated PAHs (Cl-PAHs).A clean-up method for Cl-PAHs in ambient air samples was developed. This involves back-flush HPLC with a cyanopropyl-bonded stationary phase for isolation of chloro-added PAHs and a two-dimensional HPLC back-flush method, utilizing coupled nitrophenylpropylsilyl and 2-(l-pyrenyl)ethylsilyl columns, for isolation of chloro-substituted PAHs.Several chloro-substituted PAHs, of which some have shown significant mutagenic effects on Salmonella typhimurium bacterial strains in the Ames assay, were identified and quantified in urban air. Further, chloro-substituted PAHs which may derive from biologically active and highly unstable chloroadded derivatives were detected. The postulation that automobile traffic is a major source of chlorinated PAHs in urban air, was supported by the higher levels detected of these in samples from an intensively trafficked road tunnel. Furthermore, the concentration profiles of the Cl-PAHs detected in the road tunnel and in the urban air showed large similarities.An LC-GC-MS method was developed for on-line clean-up and analysis of Cl-PAHs in order to facilitate analysis of small air volumes. The method showed high reproducibility and precision and could be applied to personal exposure measurements in work environment. Determinations were made on exposure of bus drivers, with driving routes located in the inner part of Stockholm. Four chlorosubstituted PAHs, of which two monochloropyrenes were quantified, were detected in the samples.