A study for kinetics and oxidation reaction of substituted benzyl alcohols using Cr(VI)-6-methylquinoline

초록

6-MQCC (Cr(VI)-6-methylquinoline) complex was synthesized by the reaction of 6-methylquinoline with chromium(VI) trioxide in 6 M HCl. The structure was characterized using IR (Infrared Spectroscopy) and ICP (Inductively Coupled Plasma) analysis. The oxidation of benzyl alcohol using 6-MQCC in various solvents showed that the reactivity increased with the increase of the dielectric constant, in descending order of DMF > acetone > chloroform > cyclohexene. In the presence of DMF solvent with acidic catalyst such as sulfuric acid (H<inf>2</inf>SO<inf>4</inf> solution), 6-MQCC oxidized benzyl alcohol (H) and its derivatives (p-OCH<inf>3</inf>, m-CH<inf>3</inf>, m-OCH<inf>3</inf>, m-Cl, m-NO<inf>2</inf>) were effectively oxidized. Electron-donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (ρ) was-0.69 (308 K). The observed experimental data was used to rationalize the fact that the hydride ion transfer occurred at the rate-determining step. © 2015, Korean Society of Industrial Engineering Chemistry. All right reserved.

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