In this study, the transformation of 1-naphthol via oxidative-coupling reaction was investigated using Mn oxides. 1-Naphthol was transformed completely by birnessite, which is one of the natural Mn oxides present in soil. The surface area-normalized specific rate constant, k(surf), for 1-naphthol was determined to be 9.66 x 10(-4) L/m(2) min using observed pseudo-first-order rate constants with respect to birnessite loading. The transformation of 1-naphthol was dependent on the solution pH, and the pseudo-first-order rate constants increased from 0.028 at pH 11 to 0.075 at pH 2 at a birnessite loading of 0.625 g/L. GC and LC mass spectroscopic analysis of the supernatants were performed after separating the reaction solution into hydrophobic and hydrophilic fractions by solvent extraction. The major transformation products were found to be 1,4-naphthoquinone(1,4-NPQ) and naphthol polymerized products with a molecular weight (m/z) ranging from 400 to 2000. Transformation of 1,4-NPQ, to the polymerized products by an additional birnessite loading was also verified. The DOC concentrations of the supernatants before and after the reaction were analyzed and the rate of oligomeric precipitate formation was measured. (C) 2008 Elsevier B.V. All rights reserved.