Kinetics and mechanism of the catalytic oxidation of cyclopentene to glutaraldehyde with aqueous hydrogen peroxide

Kinetics and mechanism of the catalytic oxidation of cyclopentene to glutaraldehyde by aqueous hydrogen peroxide have been studied. In tungstic acid-t-butanol system, cyclopentene is first oxidized to cyclopentene oxide almost quantitatively, which is then transferred into an intermediate. The intermediate, which is separated and identified as β-hydroxycyclopentylhydroperoxide, can easily change into glutaraldehyde during purification. The study shows that during the formation of the intermediate two by-products are also formed. These three reactions are found to be of first-order parallel reactions. The effects of temperature and concentration of tungstic acid, hydrogen peroxide, water and t-butanol on the reaction rates have been studied. A suitable mechanism for the reaction has been proposed.