Condensation reactions of phenolic resins. 1. Kinetics and mechanisms of the base-catalyzed self-condensation of 2-hydroxymethylphenol

There are many discrepancies in the interpretations of the condensation of hydroxymethylphenols. Further investigation, reexamination of the kinetics in particular, is needed to clarify the reaction mechanisms. In this paper, the kinetic aspects of the base-catalyzed self-condensation of 2 hydroxymethylphenol (2-HMP) are discussed. The order of reaction was determined from the dependence of the initial rate of reaction on the initial concentration of 2-HMP. It was confirmed that the reaction is kinetically of genuine first-order. Consequently, any S(N)2 mechanisms must be ruled out. A quinone methide intermediate hypothesis seems to hold: the dependence of reaction rate on the NaOH/2-HMP molar ratio could be explained kinetically based on the hypothesis. (C) 2001 Elsevier Science Ltd. All rights reserved.