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Organocatalyzed Beckmann Rearrangement of Cyclohexanone Oxime by Trifluoroacetic Anhydride in a Microreactor
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  • Chencan Du,
  • Yubin Wang,
  • Jian Deng,
  • Guangsheng Luo
Chencan Du
Tsinghua University

Corresponding Author:ducc2015@139.com

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Yubin Wang
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Jian Deng
Tsinghua University
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Guangsheng Luo
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Abstract

An efficient method for the Beckmann rearrangement of cyclohexanone oxime (CHO) catalyzed by trifluoroacetic anhydride (TFAA) is proposed in this work. The effects of experimental parameters on the reaction rate are studied, including CHO concentration, TFAA/CHO ratio, temperature, and CPL concentration. The reaction rate shows a linear relationship with TFAA/CHO ratio and reduces with the increasing of CPL concentration. Based on the experimental data and the study of in-situ FTIR, a reaction mechanism is proposed and the equilibrium relationship between CPL and TFAA is established. A rate constant model is developed and is in good agreement with the experimental results. The TFAA/TFA catalytic system allows high conversion and reaction rate compared with other organic acids.
29 Jun 2022Published in Industrial & Engineering Chemistry Research volume 61 issue 25 on pages 8714-8723. 10.1021/acs.iecr.2c01078