Groundwater contamination by organic bases derived from coal‐tar wastes

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Abstract
A fluid sample from a shallow aquifer contaminated by coal‐tar wastes was analyzed for organic bases. The sample consisted of a mixture of aqueous and oily‐tar phases. The phases were separated by centrifugation and filtration. Organic bases were isolated from each phase by pH adjustment and solvent extraction. Organic bases in the oily‐tar phase were further purified by neutral‐alumina, micro‐column adsorption chromatography. Separation and identification of the organic bases in each phase were achieved by using capillary gas chromatography‐mass spectrometry‐computer (GC‐MS‐COM) and probe distillation‐high resolution mass spectrometry (PD‐HRMS) techniques. Organic bases present in the aqueous phase included primary aromatic amines (such as aniline, alkylated anilines, and naphthylamines) as well as azaarenes (such as alkylated pyridines, quinolines, acridine, and benzoquinolines). The oily‐tar phase contained acridine, benzacridines, dibenzacridines, and numerous other azaarenes, the elemental compositions of which were determined by PD‐HRMS. Azaarenes in the oily‐tar phase, varying in size from 6 to 12 rings, are reported for the first time. The origin and environmental significance of these compounds are discussed.