SCI和EI收录∣中国化工学会会刊

Chinese Journal of Chemical Engineering ›› 2013, Vol. 21 ›› Issue (12): 1404-1409.DOI: 10.1016/S1004-9541(13)60643-6

• 材料与产品工程 • 上一篇    下一篇

Synthesis of ε-Caprolactone by Oxidation of Cyclohexanone with Monoperoxysuccinic Acid

陈建, 赵小双, 张光旭, 陈波, 蔡卫权   

  1. School of Chemical Engineering, Wuhan University of Technology, Wuhan 430070, China
  • 收稿日期:2012-08-21 修回日期:2012-12-04 出版日期:2013-12-28 发布日期:2013-12-27
  • 通讯作者: ZHANG Guangxu

Synthesis of ε-Caprolactone by Oxidation of Cyclohexanone with Monoperoxysuccinic Acid

CHEN Jian, ZHAO Xiaoshuang, ZHANG Guangxu, CHEN Bo, CAI Weiquan   

  1. School of Chemical Engineering, Wuhan University of Technology, Wuhan 430070, China
  • Received:2012-08-21 Revised:2012-12-04 Online:2013-12-28 Published:2013-12-27
  • Contact: ZHANG Guangxu

摘要: In the absence of catalyst, 70% hydrogen peroxide was used to oxidize succinic anhydride to solid monoperoxysuccinic acid (PSA). Then PSA was applied to synthesis of ε-caprolactone (ε-CL) by oxidation of cyclohexanone in the heterogeneous system. In order to achieve material recycle, solid precipitated in the process of synthesizing ε-CL was dehydrated via reactive distillation followed by recrystallization to prepare succinic anhydride, which was characterized by IR (infrared spectra) and 1HNMR (1H nuclear magnetic resonance). Effects of molar ratio of PSA to cyclohexanone, acetic acid dosage, reaction temperature, reaction time on conversion of cyclohexanone, yield and selectivity of ε-CL were investigated respectively. The results indicated that conversion of cyclohexanone, yield and selectivity of ε-CL were upto 98.1%, 97.5% and 99.4% respectively under the optimal conditions. In addition, in the process of synthesizing succinic anhydride, the optimal yield of succinic anhydride reached 67.4%.

关键词: monoperoxysuccinic acid, cyclohexanone, &, epsilon, -caprolactone, reactive distillation, recrystallization

Abstract: In the absence of catalyst, 70% hydrogen peroxide was used to oxidize succinic anhydride to solid monoperoxysuccinic acid (PSA). Then PSA was applied to synthesis of ε-caprolactone (ε-CL) by oxidation of cyclohexanone in the heterogeneous system. In order to achieve material recycle, solid precipitated in the process of synthesizing ε-CL was dehydrated via reactive distillation followed by recrystallization to prepare succinic anhydride, which was characterized by IR (infrared spectra) and 1HNMR (1H nuclear magnetic resonance). Effects of molar ratio of PSA to cyclohexanone, acetic acid dosage, reaction temperature, reaction time on conversion of cyclohexanone, yield and selectivity of ε-CL were investigated respectively. The results indicated that conversion of cyclohexanone, yield and selectivity of ε-CL were upto 98.1%, 97.5% and 99.4% respectively under the optimal conditions. In addition, in the process of synthesizing succinic anhydride, the optimal yield of succinic anhydride reached 67.4%.

Key words: monoperoxysuccinic acid, cyclohexanone, &, epsilon, -caprolactone, reactive distillation, recrystallization