Coupling products of three major phenols appearing in the waste streams of shale oil production from kukersite oil shale were isolated and analysed using high-resolution mass spectrometry (HRMS). The pattern of water-soluble phenols in retorted kukersite semi-coke leachate changes quickly during weathering. The amount of phenols decreases, but the rate of disappearance is dissimilar for different constituents. Oxidation experiments with three major phenols (resorcinol, 5-methyl resorcinol, and 2,5-dimethylresorcinol) and their mixtures in pairs were performed in a reaction medium similar to semi-coke leachate. Reaction products were detected using silica gel thin layer chromatography (TLC) and isolated for further analysis by silica gel dry-column chromatography. The composition of primary reaction products was confirmed by nuclear magnetic resonance (NMR) spectroscopy. The primary coupling products of the studied resorcinols included the corresponding dimeric mono- and diquinones. Further coupling brought about the formation of water-insoluble products, which is the reason for the disappearance of resorcinols from the leachate.
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