Mechanism of formaldehyde adsorption of (+)-catechin

The reaction of (+)-catechin with formaldehyde vapor was investigated as a model reaction of formaldehyde adsorption of (+)-catechin. It was found by H nuclear magnetic resonance spectroscopy, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and gel permeation chromatography of the product that the vapor reaction of (+)-catechin with formaldehyde without a solvent or a catalyst proceeds via methylolation, condensation, and polymerization. This is the same as the reaction in a solvent in the presence of an acid or a base. The formation of polyoxymethylenes such as paraformaldehyde was not confirmed.