Abstract
The kinetics of the Friedel-Crafts reaction of chlorobenzene with each one of cyanuric chloride and 2, 4-dichloro-6-methoxy-s-triazine (DCMT) were investigated. In all cases, large excess of chlorobenzene was used, and theprogressof reaction was followed by measuring the hydrogen chloride formed. Three chlorines of cyanuric crhloride were thus reacted with chlorobenzene by consecutive reactions, and the apparent velocity constants k1 's at 100, 110, and 120°C in the first step were found to be 1.34 × 10-3, 1.89 × 10-3, and 2.18 × 10-3 (min-1), respectively. The relative ratio of rate constants in the three steps was approximately k1 : k2 : k3=3 : 2 : 1. In the reaction of chlorobenzene with DCMT, it was found that the yield of the condensed products increased with an increasing amount of anhydrous aluminum chloride used, and one mole of anhydrous aluminum chloride consumed for the demethylation of DCMT.
