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Electrosynthesis of sodium hypochlorite in room temperature ionic liquids and in situ electrochemical epoxidation of olefins

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Abstract

Asymmetric electro-epoxidation of olefins had been achieved with sodium hypochlorite (NaClO) as an oxidant, which was generated by electrolysis in two-phase systems of aqueous sodium chloride (NaCl) and ionic liquids (1-butyl-3-methylimidazolium hexafluorophosphate (BMImPF6) and 1-butyl-3-methylimidazolium tetrafluoroborate (BMImBF4)). The electrolysis conditions by different current densities (0.8, 0.9, 1.0, 1.1 and 1.3 mA/cm2) and pH values (8, 9, 10, 11, 12 and 13) were optimized and 1.1 mA/cm2 and pH 11 were selected. The proposed reaction mechanism is also discussed. The performance of new catalytic systems in four kinds of reaction media in the presence or absence of ammonium acetate (NH4OAc) as a cocatalyst was investigated systematically. Compared to the chemical epoxidation systems, the enantiomeric excess (ee) values and yields for the epoxidation of styrene, α-methylstyrene and indene were acceptable in the electrocatalytic epoxidation systems.

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Acknowledgments

The authors are grateful to the Chairperson Foundation of Xi’an Jiaotong University for financial support and Prof. Yuhai Tang for helpful discussions in chiral HPLC separations.

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  1. Institute of Analytical Sciences, School of Science, Xi’an Jiaotong University, Xi’an, Shaanxi, 710061, China

    Ruiqin Zhao, Yuhai Tang, Saili Wei, Xiaoqian Xu, Xiaoyu Shi & Guangbin Zhang

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  1. Ruiqin Zhao
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  2. Yuhai Tang
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Correspondence to Yuhai Tang.

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Zhao, R., Tang, Y., Wei, S. et al. Electrosynthesis of sodium hypochlorite in room temperature ionic liquids and in situ electrochemical epoxidation of olefins. Reac Kinet Mech Cat 106, 37–47 (2012). https://doi.org/10.1007/s11144-011-0403-3

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