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Synthesis, characterization and application of nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride as a highly efficient catalyst for the preparation of N,N′-alkylidene bisamides

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Abstract

A novel mesoporous nanomaterial, namely nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-[TSPSED][Cl]2), was prepared, and characterized using Fourier-transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDS), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), adsorption/desorption porosimetry (BET, Langmuir, BJH and adsorption/desorption isotherm), thermal gravimetric (TG), differential thermal gravimetric (DTG) and X-ray diffraction (XRD) analyses. Afterward, nano-[TSPSED][Cl]2 was used as a highly efficient and recyclable nanocatalyst for the condensation reaction of primary amides (2 eq.) with arylaldehydes (1 eq.) under solvent-free conditions to afford N,N′-alkylidene bisamides in high yields and in short times.

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Acknowledgements

The authors gratefully acknowledge support of this work by Payame Noor University.

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  1. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    Abdolkarim Zare, Masoud Sadeghi-Takallo, Mostafa Karami & Alireza Kohzadian

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  1. Abdolkarim Zare
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  4. Alireza Kohzadian
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Correspondence to Abdolkarim Zare.

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The online version of this article (https://doi.org/10.1007/s11164-019-03775-7) contains supplementary material (the BET, Langmuir, BJH and adsorption–desorption isotherm plots of the used nano-silica for the preparation of nano-[TSPSED][Cl]2, and selected spectral data and original spectra of N,N′-alkylidene bisamides), which are available to authorized users (DOCX 506 kb)

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Zare, A., Sadeghi-Takallo, M., Karami, M. et al. Synthesis, characterization and application of nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride as a highly efficient catalyst for the preparation of N,N′-alkylidene bisamides. Res Chem Intermed 45, 2999–3018 (2019). https://doi.org/10.1007/s11164-019-03775-7

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