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Efficient and convenient oxidation of cyclohexene to adipic acid with H2O2 catalyzed by H2WO4 in acidic ionic liquids

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Abstract

A simple, efficient, and eco-friendly catalytic system for the oxidation of cyclohexene to adipic acid with H2O2 catalyzed by H2WO4 in Brønsted acidic ionic liquids under solvent-free conditions has been developed. Reaction conditions such as the catalysts, the types of anions and cations for Brønsted acidic ionic liquids, reaction temperature, and the amount of hydrogen peroxide, were investigated. Moreover, the Hammett acidity functions (H 0) of Brønsted acidic ionic liquids were determined using UV–visible spectrophotometry. The optimum reaction condition identified was n(H2WO4):n(Brønsted acidic ionic liquids):n(cyclohexene):n(H2O2) = 0.02:0.02:1:4.4, and the yield of adipic acid was 96% under the reaction scale of 10 mmol. The catalytic system can be easily recovered and reused for four reaction runs without significant loss of catalytic activity. Simple operation of the catalyst system and avoidance of the emission of nitrous oxide are the benefits of this work.

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Acknowledgements

This work was supported by the Qian-Lan Project of Jiangsu Province, the Natural Science Foundation of Jiangsu Province (No. BK20140460), the University Science Research Project of Jiangsu Province (No. 17KJD150008) and the Excellent Specialties Program and Development of Jiangsu High Education Institutions (PPZY2015B113).

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Authors and Affiliations

  1. College of Chemical and Environmental Engineering, Yancheng Teachers University, Kaifang Dadao Rd. 50, Yancheng, 224002, Jiangsu, China

    Bingtong Wang, Zongbin Zhang, Xinyu Zhang, Shixin Sun, Lin Wu & Rong Xing

  2. College of Chemistry and Chemical Engineering, Nanjing Tech University, Nanjing, 210009, Jiangsu, China

    Bingtong Wang, Zongbin Zhang & Xinyu Zhang

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  1. Bingtong Wang
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  2. Zongbin Zhang
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  3. Xinyu Zhang
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  4. Shixin Sun
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  5. Lin Wu
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Correspondence to Rong Xing.

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Wang, B., Zhang, Z., Zhang, X. et al. Efficient and convenient oxidation of cyclohexene to adipic acid with H2O2 catalyzed by H2WO4 in acidic ionic liquids. Chem. Pap. 72, 643–649 (2018). https://doi.org/10.1007/s11696-017-0303-8

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