INFLUENCE OF ALCOHOLS UPON THE UNCATALYZED REACTION BETWEEN RESORCINOL AND FORMALDEHYDE

The rate of the condensation of an uncatalyzed, equimolecular solution of resorcinol and formaldehyde in water was determined at 60°C. By replacing a portion of the water in this system with aliphatic alcohols, a reduction in the rates of condensation was noted at the same temperature. However, these reaction rates were found to vary widely among themselves, depending on the alcohol used. These results are explained under the assumption of the intermediate formation of hemiacetals from the free formaldehyde and the alcohols. The retarding effect of these alcohols on the resorcinol-formaldehyde condensation is inversely related to their different tendency to form esters with acids, or acetals with aldehydes, as reported by other authors. The general importance of the formation of hemiacetals is emphasized where formaldehyde is applied in the presence of alcohols.