THE KINETICS AND MECHANISM OF THE REACTION BETWEEN 1-CHLORO-2,3-EPOXYPROPANE AND P-CRESOL IN THE PRESENCE OF BASIC CATALYSTS

Rate constants For the reaction of 1-chloro-2,3-epoxypropane with p-cr esol in the presence of basic catalysts were studied at the temperatur e range of 71-100 degrees C. It was found that in the presence of sodi um p-cresolate, three consecutive reactions proceeded giving the follo wing products: 1-chloro-3-(tolyloxy)-2-propanol (CTP), 1-(p-tolyloxy)2 ,3-epoxypropane (TEP) as a main product, and 1,3-di(p-tolyloxy)-2-prop anol (DTP). Their rate constants at 71 degrees C were: k(1)=0.030+/-0. 009, k(2)=1.58+/-0.02, and k(3)=0.033+/-0.005 dm(3)/mol . min, respect ively. In the presence of quaternary ammonium salts, this process cons isted of 5 reactions which led to CTP as a main product as well as TEP and 1,3-dichloro-2-propanol (DCP). The rate constant of CTP formation at 71 degrees C was established, k(1)=0.130+/-0.030 dm(3)/mol . min, as were the ratios of the other rate constants k(2)/k(-4)=1.5+/-0.2, k (5)/k(4)=20.0+/5.0, and k(4)/k(1) =0.6+/-0.7. Based on the changes in Cl- ion concentration during the reaction, the catalystic activity of quaternary ammonium salts was explained. The kinetic model of these re actions in the presence of basic catalysts has been proposed and appro priate kinetic equations have been presented. (C) 1997 John Wiley & So ns, Inc.