Selective oxidation of cyclopentene with H2O2 by using H3PW12O40 and TBAB as a phase transfer catalyst

doi:10.1016/j.cjche.2018.10.014

中国化学工程学报 ›› 2019, Vol. 27 ›› Issue (8): 1851-1856.DOI: 10.1016/j.cjche.2018.10.014

Selective oxidation of cyclopentene with H₂O₂ by using H₃PW₁₂O₄₀ and TBAB as a phase transfer catalyst

Yaling Luo^1,2, Changjun Liu¹, Hairong Yue¹, Siyang Tang¹, Yingming Zhu¹, Bin Liang¹

1 Low-carbon Technology and Chemical Reaction Engineering Laboratory, School of Chemical Engineering, Sichuan University, Chengdu 610065, China;
2 School of Chemical Engineering, Northwest Minzu University, Lanzhou 730000, China

收稿日期:2018-07-19 修回日期:2018-10-11 出版日期:2019-08-28 发布日期:2019-11-16
通讯作者: Bin Liang
基金资助:
Supported by the National Natural Science Foundation of China (21406146).

Selective oxidation of cyclopentene with H₂O₂ by using H₃PW₁₂O₄₀ and TBAB as a phase transfer catalyst

Yaling Luo^1,2, Changjun Liu¹, Hairong Yue¹, Siyang Tang¹, Yingming Zhu¹, Bin Liang¹

1 Low-carbon Technology and Chemical Reaction Engineering Laboratory, School of Chemical Engineering, Sichuan University, Chengdu 610065, China;
2 School of Chemical Engineering, Northwest Minzu University, Lanzhou 730000, China

Received:2018-07-19 Revised:2018-10-11 Online:2019-08-28 Published:2019-11-16
Contact: Bin Liang
Supported by:
Supported by the National Natural Science Foundation of China (21406146).

摘要/Abstract

摘要： The selective oxidation of cyclopentene by aqueous H₂O₂ using H₃PW₁₂O₄₀ and tetrabutyl ammonium bromide (TBAB) as a phase transfer catalyst has been investigated. The results show that the presence of TBAB significantly improved the oxidation selectivity of cyclopentene. The effects of the reaction conditions on the conversion of cyclopentene were investigated in detail. The optimal reaction conditions are as follows:the H₃PW₁₂O₄₀ to TBAB molar ratio, 1:1-1:3; H₃PW₁₂O₄₀ to cyclopentene molar ratio, 0.54:100-0.64:100; and molar ratio of H₂O₂ to cyclopentene, 1.6:1. The conversion reached to 59.8% in 4 h at 35.0℃, while the selectivity of glutaraldehyde was 38.0% and the selectivity of 1,2-cyclopentanediol was 55.6%. In addition, a route for oxidation of cyclopentene by aqueous H₂O₂ using a heteropoly acid and quaternary ammonium salt as a phase transfer catalyst was proposed.

关键词: Glutaraldehyde, Cyclopentene oxidation, Phase-transfer, Heteropoly acid

Abstract: The selective oxidation of cyclopentene by aqueous H₂O₂ using H₃PW₁₂O₄₀ and tetrabutyl ammonium bromide (TBAB) as a phase transfer catalyst has been investigated. The results show that the presence of TBAB significantly improved the oxidation selectivity of cyclopentene. The effects of the reaction conditions on the conversion of cyclopentene were investigated in detail. The optimal reaction conditions are as follows:the H₃PW₁₂O₄₀ to TBAB molar ratio, 1:1-1:3; H₃PW₁₂O₄₀ to cyclopentene molar ratio, 0.54:100-0.64:100; and molar ratio of H₂O₂ to cyclopentene, 1.6:1. The conversion reached to 59.8% in 4 h at 35.0℃, while the selectivity of glutaraldehyde was 38.0% and the selectivity of 1,2-cyclopentanediol was 55.6%. In addition, a route for oxidation of cyclopentene by aqueous H₂O₂ using a heteropoly acid and quaternary ammonium salt as a phase transfer catalyst was proposed.

Key words: Glutaraldehyde, Cyclopentene oxidation, Phase-transfer, Heteropoly acid

Yaling Luo, Changjun Liu, Hairong Yue, Siyang Tang, Yingming Zhu, Bin Liang. Selective oxidation of cyclopentene with H₂O₂ by using H₃PW₁₂O₄₀ and TBAB as a phase transfer catalyst[J]. 中国化学工程学报, 2019, 27(8): 1851-1856.

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Selective oxidation of cyclopentene with H₂O₂ by using H₃PW₁₂O₄₀ and TBAB as a phase transfer catalyst

Selective oxidation of cyclopentene with H₂O₂ by using H₃PW₁₂O₄₀ and TBAB as a phase transfer catalyst

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