A systematic study of the effects of solvents on phenanthrene photooxidation

Abstract

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. (C) 2019 Elsevier Ltd. All rights reserved.