J. Technology and Education, Vol.22, No.2, pp.29-34(2015)

研究論文

Br^-イオン共存下における酸素分子の還元活性化によるシクロヘキセンの

電解酸化

 

津田 良弘^*、坪川 翼、山口 晃寛

福井工業高等専門学校　物質工学科（〒916-8507 鯖江市下司町）

*tsuda@fukui-nct.ac.jp

 

Electrocatalytic oxidation of cyclohexene with an active oxygen species produced

by reducing dioxygen in the presence of Br^- ions

 

Yoshihiro TSUDA*, Tsubasa TSUBOKAWA and Akihiro YAMAGUCHI

Department of Chemistry and Biology, National Institute of Technology, Fukui College

　(Geshi-cho, Sabae-shi, Fukui 916-8507, Japan）

 

(Received October 5, 2015; Accepted November 16, 2015)

 

Abstract

Electrocatalytic oxidation of cyclohexene to cyclohexene oxide (epoxide) and 2-cyclohexene-1-one (1-one) produced by adding a Br^- ion to an air-equilibrated acetonitorile containing cyclohexene as a substrate, hexylviologen as an electron mediator, and benzoic anhydride as an activating reagent. Increasing the concentration of Br^- ions increased the amount of the epoxide produced, but the amount of 1-one produced had a maximum value at the electrode potential of -0.77 V. The active oxygen species for producing 1-one and that for producing epoxide may be a hypobromous radical (BrO^.), produced by a reaction between a benzoyl peroxyl radical (C₆H₅COOO^.) and a Br^- ion, and a hypobromous anion (BrO^-), produced by a reaction between a benzoyl peroxide anion (C₆H₅COOO^-) and a Br^- ion, respectively.

Key words: active oxygen species, electrocatalytic oxidation, Br^- ions