Alkali catalyzed phenol formaldehyde reaction – part II. Formation of dimethylol phenols

Abstract

AbstractThe kinetic study has been made of the sodium hydroxide‐catalyzed interaction of o‐ and p‐methylol phenols with formaldehyde to give dimethylol phenols. At 0.006 M NaOH and within less than 10% of the reaction, first order kinetic behaviour was obtained. The rate constant, at 80°C., for the formation of 2,4‐dimethylol phenol from p‐methylol phenol and formaldehyde, was found to be 1.17·10−5 sec−1 and the activation energy, 23.92 kcal/mole, whereas for formation of 2,6‐ and 2,4‐dimethylol phenols from o‐methylol phenol, the rate constants were respectively 0.55 and 1.11·10−5 sec −1, the corresponding activation energies being, 25.10 and 23.37 kcal/mole. In terms of these data and those present in Part I, the relative reactivites of the free ortho and para positions in phenol and substituted phenols are evaluated and shown to be, unlike those reported by FREEMAN et al.5, consistent among themselves and with theoretical requirements.