Collect. Czech. Chem. Commun. 1986, 51, 1656-1664

Synthesis of N-hydroxymethylacrylamide in an aqueous solution

Alois Matějíček and Jaroslav Černý

Research Institute of Synthetic Resins and Lacquers, 532 07 Pardubice


The paper deals with a reaction between acrylamide and formaldehyde leading to the synthesis of N-hydroxymethylacrylamide. The reaction was carried out in the temperature range 303.2 to 333.2 K, pH 9.2-10.35, at the methanol concentration 0-6.5239 mol l-1 at the constant molar ratio of acrylamide to formaldehyde 1 : 1. The time dependence of the loss of formaldehyde in the reaction mixture was approximated by an empirical relation (cF)0 - cF = t/(A + Bt), which was used in the determination of the rate constants for a reaction leading to the synthesis of N-hydroxymethylacrylamide and for the reversible reaction, and of the equilibrium constant of the reaction. The measurements and calculations showed that the optimal conditions for the synthesis of N-hydroxymethylacrylamide were 313.2 K, methanol concentration 1.5 mol l-1 and pH 9.8-10.1.