Petroleum Chemistry, Vol.50, No.6, 437-441, 2010
Oxidative transformations of p-chloro- and p-fluorostyrene epoxides in the presence of p-toluenesulfonic acid
Mild oxidation of two halogenated styrene epoxides, 2-(4-chlorophenyl)oxirane (CSE) and 2-(4-fluorophenyl)oxirane (FSE), was studied in the presence of p-toluenesulfonic acid (TSA). Hydrogen peroxide and p-chlorobenzaldehyde are the products of CSE oxidation. The kinetics of the overall CSE consumption and oxidation of CSE and FSE are identical to those revealed earlier for the oxidation of styrene epoxide (SE). The consumption and oxidation rates do not depend on the epoxide concentration (zero order) and are proportional to the TSA concentration. At 343 K, the oxidation rate of CSE and FSE are higher than that for SE by factors of 2 and 7, respectively. The introduction of the halogen atoms in the p-position on the phenyl ring accelerates the oxidation.