Kinetic Studies on the Reactivity of Three Side-chain Functional Groups on Triesters of lsocyanuric Acid

Abstract

The three step alkaline hydrolysis of tris(2-acetoxyethyl)isocyanurate (TAEIC), tris(methoxycarbonylmethyl)isocyanurate (TMCMIC) and tris(2-methoxycarbonylenthyl)isocyangrurate (TMCEIC), and the three step reaction of tris(2, 3-epoxypropyl)isocyanurate (TEPIC) with either substituted benzoic acids or sodium thiosulfate have been investigated under various conditions.The three rate constants have been determined by use of the general method of calculating the rate constants for a three-step consecutive-competitive second-order reaction of the type A+B → C+F, A+C → D+F, A+D → E+FIt was observed that in the hydrolysis of TAEIC and in the reaction between TEPIC apd substituted benzoic acids, the ratio of k1/k3 and k2/k3 were 3 and 2, respectively, whereas in the hydrolysis of TMCMIC and TMCEIC and in the reaction of TEPIC with sodium thiosulfate, the ratio were as follows; k1/k3> 3 and k2/k3> 2. The experimental observantion can be explained on the basis of the isocyanurate-ions or neutral molecules in the several steps.