Kinetics and mechanism of formation of polymeric products during the hydroxyalkylation of parabanic acid with oxiranes

The kinetics of the reaction between N‐(2‐hydroxyalkyl) hydroparabanates (HAHP) and N,N′‐bis(2‐hydroxyalkyl) parabanates (HAP) with ethylene and propylene oxides were studied. The addition of oxiranes to imide function of HAHP led to the formation of HAP. Further reaction of HAP with oxiranes resulted in trioxoimidazolidine ring opening and polymeric products. The kinetics of the system was studied in detail. Based on the final kinetic equations, the mechanism of the reactions was postulated. The temperature dependences of kinetic parameters and analytical data provided experimental evidences supporting the mechanism. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 38: 399–406, 2006