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Amine Functionalized Graphene Oxide Stabilized Pickering Emulsion for Highly Efficient Knoevenagel Condensation in Aqueous Medium

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Abstract

A Pickering emulsion catalytic system was developed using amphiphilic amine-functionalized graphene oxide (GO-NH2) for a Knoevenagel condensation in aqueous medium instead of organic solvent. The properties of GO-NH2 and the Pickering emulsion stabilized by GO-NH2 were characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD) analysis, X-ray photoelectron spectroscopy (XPS), organic elemental analysis (OEA), contact angle (CA), Brunauer–Emmett–Teller surface area, and optical microscopy. The results indicated that the properties of the as-prepared Pickering emulsion system, such as droplet density, size, and distribution, were greatly affected by the amount of GO-NH2 and the oil–water ratio, which were closely related to the catalytic performance for Knoevenagel condensation reactions. Furthermore, this Pickering emulsion system for the Knoevenagel condensation in an aqueous medium exhibited a much higher catalytic activity than those of GO-NH2 in organic solvents under the same reaction conditions. The reaction rate constant (k) in the Pickering emulsion system was calculated to be 0.043 min−1 at 50 °C. The enhanced activity of the Pickering emulsion was mainly attributed to large interfaces between GO-NH2 and reactants in the emulsion, and the clear confinement effect. Furthermore, GO-NH2 remained stable for preparing Pickering emulsion systems after recycling in six runs, exhibiting its good reusability.

Graphic Abstract

A novel Pickering emulsion catalytic system was developed using amphiphilic amine functionalized graphene oxide (GO-NH2) for Knoevenagel condensation in aqueous medium instead of organic solvents. It exhibited excellent catalytic performance in the reaction.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21673024 and No. 21676029). The financial support from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) is also acknowledged.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, 213164, China

    Jie Zhu, Fei Wang, Dongsheng Li, Jie Zhai, Ping Liu, Weihong Zhang & Yongxin Li

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  1. Jie Zhu
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  2. Fei Wang
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  3. Dongsheng Li
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  4. Jie Zhai
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  5. Ping Liu
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  6. Weihong Zhang
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  7. Yongxin Li
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Correspondence to Yongxin Li.

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Zhu, J., Wang, F., Li, D. et al. Amine Functionalized Graphene Oxide Stabilized Pickering Emulsion for Highly Efficient Knoevenagel Condensation in Aqueous Medium. Catal Lett 150, 1909–1922 (2020). https://doi.org/10.1007/s10562-020-03103-4

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  • DOI: https://doi.org/10.1007/s10562-020-03103-4

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