Identification of primary aromatic amines in mutagenically active subfractions from coal liquefaction materials

Gas-chromatographic mass spectral (GCMS) analyses were performed on mutagenically active components from the basic, basic tar and neutral tar subfractions of a coal-derived liquid heavy distillate. The latter material is a component fraction of an experimental oil produced in a solvent refined coal process (SRC II) pilot plant. Mutagenicity was determined with the Ames/Salmonella assay system. Thin-layer chromatography (TLC) was used to separate mutagenically active components of the basic, basic tar and neutral tar fractions from some of the other compounds contained in these complex materials. For the 3 fractions tested, mutagenic activity was localized in approx. the same TLC regions, with relative mobilities (Rf) ranging from 0.1 to 0.3. GCMS analysis of the TLC regions showed that the concentrations of primary aromatic amines, as obtained by measuring peak areas for the (M + 1)+ ion as formed in the chemical ionization mode, followed essentially the same distribution as the mutagenic activity. Primary aromatic amines identified in the active regions included aminonaphthalenes, aminoanthracenes, aminophenanthrenes, aminopyrenes and aminochrysenes. With the exception of small amounts of aminonaphthalene, primary aromatic amines were not found in TLC regions that lacked mutagenic activity.