STUDIES ON THE OXIDATION OF ALPHA-SUBSTIT UTED STYRENES .1. REACTIVITY AND FORMATION OF REACTION-PRODUCTS DURING THE OXIDATION OF STYRENE DERIVATIVES

The liquid phase oxidation of alpha-tert. -butyl-, alpha-bromo-, alpha -chloro-, and alpha-methyl styrene with pure oxygen was investigated i n a closed apparatus in chlorobenzene solution and in presence of cume ne and of cumene hydroperoxide in the temperature range 35-125 degrees C. The product yields were determined gaschromatographically. The dif ferences of the activation energies of the epoxide formation and the p arallel reactions were calculated. They amount to 27-38 kJ/mol. The ep oxide selectivity increases with increasing temperature and decreases with increasing concentration of cumene. Relative chain propagation co nstants related to the tertiary CH-bond of cumene were determined from cooxidation experiments.