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Diacidic ionic liquid supported on magnetic-silica nanocomposite: a novel, stable, and reusable catalyst for selective diester production

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Abstract

Abstract

Supported diacidic ionic liquid on magnetic silica nanoparticles (SDAIL@magnetic nanoSiO2) was successfully prepared through a multi-step approach. 2,2- bis ((3- methylimidazolidin-1-yl) methyl) propane- 1,3- diol bromide salt was immobilized onto the surface of magnetic silica nanoparticles via covalent bonding to prepare a novel powerful acidic catalyst. The synthesized catalyst was characterized by FT-IR, SEM, TGA, VSM, N2 adsorption–desorption measurements and acid-base titration. The catalytic activity of the prepared SDAIL@magnetic nanoSiO2 was investigated for the selective diesterification of alcohols by phthalic anhydride to afford corresponding dialkyl plasticizers under solvent-free conditions. The nature of two acidic counter anions as well as the presence of Lewis acidic species (Fe3O4) on the magnetic nanosilica and high surface area of the nanosilica influenced the behavior of the catalyst. Surperisingly, the high acidic character of the catalyst facilitates the reaction with a short reaction time. Furthermore, TG analysis strongly demonstrates that major content of IL is still stable on the support up to 290 °C, so catalyst has a good thermal stability. Under the optimized conditions, the conversion of phthalic anhydride was 100% and diester plasticizers were obtained with excellent yields (80–100%). The SDAIL@magnetic nanoSiO2 catalyst showed a good reusability and could be easily separated from the reaction mixture using an external magnet thanks to its superparamagnetic behavior and reused for several runs without significant activity loss. An important advantage of the SDAIL@magnetic nanoSiO2 was its high-hydrophilicity resulted in excellent selectivity towards the formation of only diesters which are commonly used plasticizers in different industries.

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Acknowledgements

The authors are grateful to Malek-Ashtar University of Technology for supporting this work.

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran

    Reza Fareghi-Alamdari, Mehri Nadiri Niri & Negar Zekri

  2. Center for Research and Science Education, Organization for Educational Research and Planning, Tehran, Iran

    Hassan Hazarkhani

Authors
  1. Reza Fareghi-Alamdari
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  2. Mehri Nadiri Niri
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  3. Hassan Hazarkhani
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  4. Negar Zekri
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Correspondence to Reza Fareghi-Alamdari.

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Fareghi-Alamdari, R., Nadiri Niri, M., Hazarkhani, H. et al. Diacidic ionic liquid supported on magnetic-silica nanocomposite: a novel, stable, and reusable catalyst for selective diester production. J IRAN CHEM SOC 15, 2615–2629 (2018). https://doi.org/10.1007/s13738-018-1450-8

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  • DOI: https://doi.org/10.1007/s13738-018-1450-8

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