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Abstract
Chlorinated 4,4‘-diphenoquinones, previously unknown byproducts of thermal processes in the presence of chlorine, have been discovered in a variety of samples such as oil products from a waste pyrolysis plant, a fly ash from a municipal waste incinerator, and a sample of Kieselrot slag. The pyrolysis plant products also contained tetramethylated and unsubstituted 4,4‘-diphenoquinone. All compounds may be generated by oxidative coupling of phenols at elevated temperaturesa reaction that is considered to compete with the formation of the structurally isomeric dioxins. Once built-up, 4,4‘-diphenoquinones form a redox pair with the corresponding 4,4‘-dihydroxybiphenyls, with variable equilibrium positions depending on the prevailing conditions. For analysis, a cleanup method which involves liquid/liquid partition and solid-phase extraction was developed. The method is suitable for the determination of all substances of this class. Quantitative analysis was carried out by HPLC using an electrochemical detector...
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