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A systematic study of the effects of solvents on phenanthrene photooxidation

Shankar, Ravi, An, Joon Geon, Loh, Andrew, Yim, Un Hyuk
Chemosphere 2019 v.220 pp. 900-909
Fourier transform infrared spectroscopy, acetonitrile, aldehydes, amides, carboxylic acids, environmental factors, exposure duration, gas chromatography-mass spectrometry, half life, hexane, iso-octanes, ketones, methanol, phenanthrenes, photooxidation, solvents
A systematic study of the photooxidation of phenanthrene under simulated environmental conditions was conducted in vitro using polar (methanol, acetonitrile) and non-polar (isooctane, hexane) solvents as media. In all solvents, phenanthrene concentration decreased exponentially as exposure time increased. Fourier-transform infrared spectroscopy (FTIR) and gas chromatography–mass spectrometry (GC–MS) analysis were used to investigate the structural changes induced by photooxidation. After 24 h of photooxidation, FTIR showed the formation of characteristic bands of carboxylic acid in all solvents. In non-polar solvents, characteristic phenanthrene peaks were completely depleted after 48 h. In polar solvents, phenanthrene peaks disappeared at a slower rate, with peaks in acetonitrile disappearing at 72 h and methanol persisting at trace levels at 96 h. The reaction rate was higher in non-polar solvents. The obtained half-lives were observed in the following order: isooctane (13.2 h) > hexane (13.5 h) > methanol (18.0 h) > acetonitrile (22.8 h). FTIR and GC–MS results were in good agreement and showed the formation of carboxylic acids, aldehydes, and ketones in polar solvents and carboxylic acids, alkanes, and alkanoic acids in non-polar solvents. Products such as primary amides induced by solvent effects were observed in acetonitrile. Based on the results, the solvents were rated and a solvent selection guide for photooxidation of PAHs was provided.