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Solvent Selective Polyacrylonitrile Fiber as a Recyclable Catalyst for the Knoevenagel-Michael Reaction in Water

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Abstract

Heterogeneous catalysis is an important branch of sustainable chemistry. In this work, a series of polyacrylonitrile fiber (PANF) fiber catalysts (PANF-E, PANF-EDs, and PANF-D) with different catalytic micro-environments are developed and characterized by elemental analysis, Fourier-transfer infrared spectroscopy, x-ray diffraction, thermogravimetric/differential scanning calorimetry analysis, scanning electron microscopy, and mechanical strength measurements to demonstrate the successful immobilization of the different amines as well as evaluate the physical strength and thermal stability of the fiber catalysts at different stages. The catalytic activities of the fiber catalysts are tested by one-pot three-component Knoevenagel-Michael reaction to the synthesis of substituted 2-amino-4H-chromenes in which the influences of surface polarities, kinds and proportions of functional groups on the fiber catalysts activities were investigated. Among the prepared catalysts, the PANF-D with higher density of tertiary amino group and hydrophilic micro-environment exhibited the best catalytic activity to efficiently catalyze the three-component reaction in water with excellent substrate suitability (92-98%). In addition, the catalyst can be easily separated from the catalytic system and conveniently reused at least ten times. Moreover, the PANF-D performs well in scaled-up experiment in a simple fixed-bed reactor with a yield of 97% which allows it to have great potential for further cleaner industrial applications.

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Acknowledgements

We gratefully acknowledge the support from the Natural Science Foundation of Henan Province (212300410318). Fundamental Research Funds of Zhongyuan University of Technology (K2020QN008), National Natural Science Foundation of China (21802034). Collaborative Innovation Centre of Henan Textile and Clothing Industry, Innovation Scientists and Technicians Troop Construction Projects of Henan Province (Grant Nos. 164100510007 and CXTD2015018), and Zhengzhou University (Grant Nos. 1421316035 and 2016xjxm258), Program for interdisciplinary Direction Team in Zhongyuan University of Technology, China.

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Authors and Affiliations

  1. College of Chemistry, Zhengzhou University, Zhengzhou, 450001, People’s Republic of China

    Pengyu Li & Weihua Chen

  2. School of Material and Chemical Engineering, Centre for Advanced Materials Research, Zhongyuan University of Technology, Zhengzhou, 450007, People’s Republic of China

    Pengyu Li, Yu Yang, Xueling Wu, Jiali Lu & Lingrui Hu

  3. Collaborative Innovation Centre of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin, 300072, People’s Republic of China

    Wenqin Zhang

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  1. Pengyu Li
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  2. Yu Yang
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10562_2021_3593_MOESM1_ESM.docx

Supplementary data associated with this article can be found, in the online version, at http://dx.doi.org. The supporting material contains the experimental details, the characterization data of compounds and the copies of 1H NMR (DOCX 922 kb)

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Li, P., Yang, Y., Wu, X. et al. Solvent Selective Polyacrylonitrile Fiber as a Recyclable Catalyst for the Knoevenagel-Michael Reaction in Water. Catal Lett 152, 43–54 (2022). https://doi.org/10.1007/s10562-021-03593-w

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