Formation of nitroarenes from the reaction of polycyclic aromatic hydrocarbons with dinitrogen pentoxide.
Reactions of six polycyclic aromatic hydrocarbons (PAH) (fluoranthene (FL), pyrene (PY), benz(a)anthracene (BaA), chrysene (CHRY), benzo(a)pyrene (BaP), and perylene (PER)), deposited on glass-fiber filters, with gaseous N/sub 2/O/sub 5/ in air were investigated in an all-Teflon chamber. Pyrene, FL, BaP, and BaA gave significant yields of nitro derivatives after only a 30-min exposure. In control exposures to NO/sub 2/ plus HNO/sub 3/ mixtures or to HNO/sub 3/ alone, the yields of nitro derivatives of PY, FL, and BaA were very low relative to those in the N/sub 2/O/sub 5/ exposures. The reactivity ranking of these PAH toward gaseous N/sub 2/O/sub 5/ was PY > FL > BaP > BaA > PER > CHRY. This order is significantly different from that previously observed for nitration of PAH deposited on glass-fiber filters and exposed to a flow of gaseous NO/sub 2/ + HNO/sub 3/ or for nitration of PAH in solution by NO/sub 2//N/sub 2/O/sub 4/ mixtures. It also differs from the reactivity ranking determined in this study for the reaction of these PAH with N/sub 2/O/sub 5/ in CCl/sub 4/ solution of PER > BaP > BaAgreater than or equal to PY > FL greater than or equal to CHRY. Environmentalmore » implications are discussed.« less