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Synthesis, Characterization, and the Study of Thermal Behavior and Catalytic Activity of a Halogen-free Dicationic Ionic Liquid

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Abstract

4,4ʹ-Trimethylenedipiperidin-N,Nʹ-diium diacetate was obtained as a cream-like liquid with a pale yellow color. Its ionic structure was demonstrated by different spectroscopic techniques, and its thermal behavior was also studied by TGA/DTA and DSC techniques to record its phase transitions and thermal stability and compare those with another analog, i.e., 1H,4H-piperazine-N,Nʹ-diium diacetate. Due to the existence of monoprotic Brönsted base and conjugate acid of TMDP in the new ionic liquid, it can act as a promising hydrogen bond catalyst. Thus, the Knoevenagel condensation of various substituted benzaldehydes with malononitrile was investigated using the new ionic liquid in ethanol. Ethanol acts as a reaction medium and crystallization solvent, and pure products were obtained directly from ethanol with no costly separation and purification. The residue solution was employed in the next run without concentration or activation. Furthermore, the model reaction was carried out on a large scale using the current catalytic process, affording a conversion of 100% and a high yield of the crystalline product even after ten consecutive runs. Energy efficiency, cost- and time-saving, and waste prevention demonstrate the newly developed metal- and halogen-free catalytic system as a more sustainable catalytic process for preparing the substituted arylidene malononitriles on the laboratory and industrial scale.

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Data Availability

Data will be made available on request. The data that support the findings of this study are available from the corresponding author upon reasonable request.

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Acknowledgements

The authors are also grateful to all staff members in the Analytical and Testing Center of Nanotechnology & Catalysis Research Center for their partial support.

Funding

This work was supported by Research Grant IF008-2023 from Nippon Sheet Glass Foundation for Materials Science and Engineering, Japan, and ST018-2022 from UM International Collaboration Grant, Universiti Malaya, Malaysia.

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Authors and Affiliations

  1. Nanotechnology and Catalysis Research Center, Institute for Advanced Studies (IAS), University of Malaya, 50603, Kuala Lumpur, Malaysia

    Lia Zaharani, Suzaimi Johari, Mohd Rafie Johan & Nader Ghaffari Khaligh

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  1. Lia Zaharani
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  2. Suzaimi Johari
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  4. Nader Ghaffari Khaligh
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Contributions

Lia Zaharani: Methodology, Investigation, Data collection, Data curation, Suzaimi Johari: Methodology, Investigation, Data collection; Mohd Rafie Johan: Resources, Supervision; Nader Ghaffari Khaligh: Conceptualization, Funding acquisition, Project administration, Resources, Supervision, Validation, Writing-original draft, Writing-review & editing.

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Correspondence to Nader Ghaffari Khaligh.

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Zaharani, L., Johari, S., Johan, M.R. et al. Synthesis, Characterization, and the Study of Thermal Behavior and Catalytic Activity of a Halogen-free Dicationic Ionic Liquid. Catal Lett (2024). https://doi.org/10.1007/s10562-024-04665-3

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