Preparation of α-Hydroxylated Acetal from 2-Butanone by Indirect Electrooxidation

Authors

Hai-qing HUANG, State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;
Ye MIAO, State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;
Xin-sheng ZHANG, State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;Follow

Corresponding Author

Xin-sheng ZHANG(xszhang@ecust.edu.cn)

Abstract

Acetoin (3-hydroxy-2-butanone) is an important food spice. As a platform compound, it is widely used in medicine, tobacco, cosmetics, chemical material and other industries. In this paper, α-hydroxylated acetal, an intermediate of acetoin, was prepared from 2-butanone by indirect electrooxidation in the plate and frame electrolytic cell, in which graphite plates were used as both an anode and a cathode, while KOH as an electrolyte and KI as a catalyst. Acetoin could be prepared by hydrolysis in acidic aqueous solution from acetoin intermediate. The effects of current density, electrolyte flow rate between the plates, 2-butanone concentration and electrolysis temperature on the yield and efficiency of acetoin intermediate were investigated. Under the optimized conditions, namely, the current density of 40 mA·cm^-2, the flow rate of 6.4 cm·s^-1, the 2-butanone concentration of 1.75 mol·L^-1, the electrolysis temperature of 30 °C, and the passed charge of 1.5 F·mol^-1, the yield and current efficiency of the acetoin intermediate could reach 78.9% and 40.1%, respectively. The cyclic voltammetric tests showed that during electrolysis, iodine ions were oxidized to iodine on the anode, while methanol was reduced to methoxy anion on the cathode. 2-butanone reacted with the electrolytic products, and eventually, the acetoin intermediate was formed.

Graphical Abstract

Keywords

2-butanone, acetoin intermediate, indirect electrooxidation, potassium iodide, methanol

DOI Link

https://doi.org/10.13208/j.electrochem.190222

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Publication Date

2020-06-28

Online Available Date

2019-04-23

Revised Date

2019-04-01

Received Date

2019-02-25

Recommended Citation

Hai-qing HUANG, Ye MIAO, Xin-sheng ZHANG. Preparation of α-Hydroxylated Acetal from 2-Butanone by Indirect Electrooxidation[J]. Journal of Electrochemistry, 2020 , 26(3): 389-396.
DOI: 10.13208/j.electrochem.190222
Available at: https://jelectrochem.xmu.edu.cn/journal/vol26/iss3/12