Reaction of Naphthalene and Its Derivatives with Hydroxyl Radicals in the Gas Phase

Abstract

Naphthalene is the most abundant polycyclic aromatic hydrocarbon (PAH) found in urban air. It is reactive in the atmosphere under ambient conditions, its chief reaction partner being the hydroxyl radical, OH • . In this work, the reactions of OH • with naphthalene, 1-and 2-naphthol, and 1-and 2-nitronaphthalene were studied in a 9.4 m 3 smog chamber. Relative rates of reaction accorded well with previous studies and allowed estimates to be made of the atmospheric lifetimes of these compounds. Numerous oxidation products were identified, and mechanisms proposed for their formation were based on the further transformation of benzocyclohexadienyl radicals formed by addition of OH • to naphthalene. The naphthols and nitronaphthalenes were deduced not to be on the major reaction pathway to the more oxidized products. Because of the high reactivity of PAH in air, we suggest that priority be given to identifying and quantitating their reaction products, some of which may be relatively persistent air toxics.

Reactive uptake of ammonia to secondary organic aerosols: kinetics of organonitrogen formation

“…Experiments were performed in a 9 m 3 cylindrical smog chamber, which has been described in detail by Bunce et al (1997). Briefly, this reactor is constructed with 50 µm FEP Teflon film and housed in an air-conditioned room (295 ± 2 K).…”

Naphthalene SOA: redox activity and naphthoquinone gas–particle partitioning

“…They may also be produced as secondary products of polycyclic aromatic hydrocarbon (PAH) oxidation. Naphthalene (Bunce et al, 1997;Chan et al, 2009;Kautzman et al, 2010;Lee and Lane, 2009;Sasaki et al, 1997), phenanthrene (Lee and Lane, 2010;Wang et al, 2007), and anthracene (Kwamena et al, 2006) all generate their corresponding quinone species (naphthoquinone, phenanthrenequinone, and anthraquinone, respectively) via reaction with gas-phase oxidants. Formation of these species from PAH precursors in the atmosphere could increase the redox activity of ambient particles during photochemical aging in locations with PAH emission sources.…”

Multidimensional Gas Chromatography - Time of Flight Mass Spectrometry of PAH in Smog Chamber Studies and in Smog Samples

“…When the fluorescent lamps were turned on, the OH radical was produced to a steady state in just a few milliseconds (Bunce et al, 1997). When the lamps were turned off, the OH radical disappeared almost as quickly, effectively stopping the reactions and freezing the product mix.…”

“…The first report of a variety of oxidized products of the reaction of Naphthalene with the OH radical in a smog chamber was published in 1994 (Lane & Tang, 1994). Numerous publications have followed, describing the products of the OH radical reactions with naphthalene (Atkinson & Arey, 1994;Bunce et al, 1997;Sasaki et al, 1997;Mihele et al, 2002;Wang et al, 2007;Lee & Lane, 2009;Nishino & Arey, 2009); with acenaphene (SauretSzczepanski & Lane, 2004); with Alkylated naphthalenes (Banceu et al, 2001;Wang et al, 2007) and with phenanthrene (Helmig & Harger, 1994;Esteve et al, 2003;.…”