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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Photo-induced OH reactions of naphthalene and its oxidation products on SiO2
C Brussol1, M Duane, P Carlier
1Joint Research Centre, European Commission, TP 290, I-21020, Ispra, VA, Italy. claire.brussol@irc.it
Abstract:
The photo-induced degradation of naphthalene, 1,4-naphthoquinone, 1-naphthol and 1-NO(2) naphthalene, adsorbed on silica gel, and with the addition of nitrogenous air pollutants e.g. NO(2) (as KNO(2)) was investigated. Results indicate that compounds adsorbed onto a solid carrier are degraded when irradiated with UV light (lambda > 290 nm) in the presence of nitrites. The key species initiating the naphthalene degradation is the OH-radical which is generated through the photolysis of NO(2). Reaction products identified were 2-formyl-cinnamaldehyde, 1,4-naphthoquinone, nitronaphthol, o-phthaldialdehyde, phthalide and nitronaphthalene. A mass balance between 40-50% was achieved. Under the same irradiation conditions, 1-NO(2) naphthalene is mainly degraded by direct photolysis while degradation of 1-naphthol and 1,4-naphthoquinone proceeds via the reaction with OH-radicals. Identified products were hydroxy-nitro-nitroso- and quinones compounds.
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