Extractive reaction for the epoxidation of cyclohexene to cyclohexene oxide using dioxirane was studied. The studies were divided into two main parts: (1) comparison of different cyclohexene oxide preparation methods and (2) effects of operating parameters such as stirring rate, type of solvent, initial solvent/aqueous ratio, temperature, pH and amount of catalyst on the performance of the extractive reaction. The results revealed that the best method was the epoxidation of cyclohexene by dioxirane in an extractive reaction system with presence of a phase transfer catalyst. A maximum conversion obtained from the system without a solvent can be exceeded with an extractive reaction process by introducing of an immiscible solvent to the system. It was found that the cyclohexene oxide yield increased with increasing stirring rate and the amount of acetone, and that the reaction system using dichloromethane showed the highest performance compared to those with toluene and benzene.