THE OZONATION OF BENZ[A]ANTHRACENE - PATHWAY AND PRODUCT IDENTIFICATION

The pathway for the ozonolysis of benz[a]anthracene (BaA) (ACS standar d named), a polycyclic aromatic hydrocarbon (PAH), has been described in this paper. BaA was dissolved in a 90% acetonitrile:water (v/v) mix ture to achieve an initial concentration of 1 mM. The ozonolysis of Ba A was evaluated using different ozone dosages. The ozonation products were identified by gas chromatography/mass spectrometry (GC/MS). Fifte en products including eight pairs of isomers were identified. Ozone re acted with BaA simultaneously by bond and atom attack. Ozone attack on the carbon at the 7 and/or 12 position produced the quinone or hydrox yl functional groups. The bond attack type of reaction occurred at the 5,6 position and caused ring cleavage resulting in phenyl-naphthyl ty pe products. Ozonolysis of BaA in this solvent mixture occurred prefer entially by bond attack rather than by the atom attack type of reactio n, (C) 1998 Elsevier Science Ltd. All rights reserved.