Chemistry of PCBs and PBBs

Introduction A recent book by Hutzinger et al. (1) reviews the chemistry of chlorinated biphenyls through the end of 1973. This wide-ranging review also includes discussions of metabolism and determination of chlorinated biphenyls. The present report reviews areas of chlorobiphenyl and bromobiphenyl chemistry held to be pertinent to the Subcommittee's concern for possible health effects of these types of compounds. No attempt at complete coverage of these subject areas is claimed. Findings reported since 1973 are particularly stressed. Nonmetabolic alteration of the halogenated biphenyls is considered in terms of agents most available to induce chemical change in the environment. Expected differences between chlorinated biphenyls and brominated biphenyls in their environmental chemistry are commented on. It is possible that certain of the chlorinated biphenyl compounds will be shown to have relatively greater potential hazard for health. Therefore , occurrence and fate in the environment and metabolism and toxic effects in animals are related to chemical structure of the biphenyls. For the general public, food is presumed to be the major source of chlorinated biphenyl compounds. The important concepts related to analytical methodology for PCB (and PBB) residues, particularly in foods, are reviewed. Alternative means of quantitation of these residues and problems in the quantitation techniques are discussed. The pertinent aspects of chlorinated dibenzofu-rans, as known contaminants in commercial PCBs and as potentially significant environmental contaminants , are reviewed. In reviewing the chemistry related to health effects of the PCBs and PBBs, it must be remembered that environmental contamination by these two commercial chemical mixtures is vastly different in magnitude. The former have been steadily released into the environment, in many countries, presumably over decades, and are now found to be a pervasive , worldwide contaminant. The number of chlorinated biphenyls reaching the environment probably number nearly 100 different compounds. The PBBs, encompassing a small number of chemical structures to begin with, are of concern due to a single, fairly recent contamination incident, apparently limited to the State of Michigan. Commerical preparation of mixtures of chlori-nated biphenyls by reaction of biphenyl with chlorine has been described by Hubbard (2). A more recent discussion of this subject, including the newer preparation designated as Aroclor 1016, is now available (3). Analysis of the chlorinated biphenyl content of various American commercial PCB mixtures (Aroclors) has been reviewed by Hut-zinger et al. (1). An estimated 40 to 60 different chlorinated biphenyl compounds are present in each …