US EPA

2471055 

Journal Article 

Dicarbonyl products of the OH radical-initiated reactions of naphthalene and the C1- and C2-alkylnaphthalenes 

Wang, L; Atkinson, R; Arey, J 

2007 

1 

Environmental Science & Technology
ISSN: 0013-936X
EISSN: 1520-5851 

41 

8 

2803-2810 

English 

17533842 

10.1021/es0628102 

WOS:000245892900031 

http://://WOS:000245892900031
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Naphthalene and the C-2- and C-2-alkylnaphthalenes are the most abundant polycyclic aromatic hydrocarbons (PAHs) in urban atmospheres. Their major atmospheric loss process is by gas-phase reaction with hydroxyl (OH) radicals. In this study, we have used in situ direct air sampling atmospheric pressure ionization mass spectrometry (API-MS) as well as gas chromatography-mass spectrometry (GC/MS) techniques to investigate the products of the gas-phase reactions of OH radicals with naphthalene, naphthalene-d(8), 1- and 2-methylnaphthalene (MN), 1- and 2-MN-d(10), 1- and 2-ethylnaphthalene (EN), and the 10 isomeric dimethy1naphthalenes (DMNs). The major reaction products are ring-opened dicarbonyls that are 32 mass units higher in molecular weight than the parent compound, one or more ring-opened dicarbonyls of lower molecular weight resulting from loss of two beta-carbons and associated alkyl groups, and ring-containing compounds that may be epoxides. Phthalic anhydride and alkylsubstituted phthalic anhydrides were observed as second generation products. The position of alkyl-substitution on the naphthalene ring is a key factor determining the ring cleavage site and the isomeric product distribution. 

Chlorine Compounds; Environmental Pollutants; Naphthalenes; naphthalene; 2166IN72UN; Hydroxyl Radical; 3352-57-6; Index Medicus; Chromatography, Gas -- methods; Mass Spectrometry -- methods; Molecular Structure; Environmental Pollutants -- chemistry; Naphthalenes -- chemistry; Chlorine Compounds -- chemistry; Hydroxyl Radical -- chemistry