Abstract
The phase-transfer catalytic epoxidation of 5-vinyl-2-norbornene under the presence of cocatalyst and oxidant agent in an organic/aqueous two-phase medium was investigated. Quaternary ammonium salts, sodium tungstate and phosphoric acid, and hydrogen peroxide were used as the phase-transfer catalyst, cocatalysts, and oxidant agent, respectively. The purpose of this work is to examine the oxidation of the two double bonds of 5-vinyl-2-norbornene and the reaction mechanism and to confirm the reaction steps. The roles of quaternary ammonium salt, sodium tungstate and phosphoric acid and hydrogen peroxide in the formation of the complex, which acts as the active intermediate, were identified from the experimental observation. Only a 2,3-epoxy-5-vinylnorbornane single product was produced from the reaction. Based on the experimental results, a rational mechanism of the catalytic epoxidation is proposed. The kinetics of the catalytic epoxidation in the two-phase solution are studied in order to obtain a rate expression. The effects of the reaction conditions, such as the amount of quaternary ammonium salts, the amount of cocatalyst with the same stoichiometric amount of hydrogen peroxide, the amount of organic solvents, the pH value, and the temperature, on the conversion were studied in detail.
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