Hydroxymethylation of Phenol Revisited: A Readjusted Mathematical Model

NICOLAU, V.; ESTENOZ, D. A.; MEIRA, G. R.

INDUSTRIAL & ENGINEERING CHEMICAL RESEARCH

AMER CHEMICAL SOC

Lugar: Washington; Año: 2013 vol. 52 p. 18140 - 18152

0888-5885

The hydroxymethylation of phenol in alkaline conditions is the first step in the synthesis of resols, which must be later cured for the production of final articles. A mathematical model for the hydroxymethylation of phenol is presented. It is based on the kinetic mechanism by Freeman and Lewis (J. Am. Chem. Soc. 1954, 76, 2080−2087) and includes a set of side reactions. Arrhenius expressions for the seven hydroxymethylation kinetic constants at pH 8−10 and temperatures 30−57 °C, and in the absence of methanol, were recalculated from the constants reported by Zavitsas et al. (J. Polym. Sci., Part A-1: Polym. Chem. 1968, 6, 2541−2559), in order to take into consideration the hydration/dehydration of formaldehyde and other side reactions. The model adequately predicts the measurements in the mentioned publications and in Higuchi et al. (J. Wood Sci. 1999, 45, 306−312). All of the kinetic parameters were directly or indirectly taken from the literature and were not readjusted to the measurements