Synthesis of new low-viscous sulfonic acid-functionalized ionic liquid and its application as a Brönsted liquid acid catalyst for the one-pot mechanosynthesis of 4H-pyrans through the ball milling process

Khaligh, Nader Ghaffari and Mihankhah, Taraneh and Johan, Mohd Rafie (2019) Synthesis of new low-viscous sulfonic acid-functionalized ionic liquid and its application as a Brönsted liquid acid catalyst for the one-pot mechanosynthesis of 4H-pyrans through the ball milling process. Journal of Molecular Liquids, 277. pp. 794-804. ISSN 0167-7322, DOI https://doi.org/10.1016/j.molliq.2019.01.024.

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Official URL: https://doi.org/10.1016/j.molliq.2019.01.024

Abstract

In the present study, a new low-viscous sulfonic acid-functionalized ionic liquid (SAIL) viz. 4,4′-trimethylene-N,N′-sulfonic acid-dipiperidinium chloride was synthesized and characterized by FTIR, 1D and 2D NMR, and Mass spectra. Then, some properties of new SAIL were determined including pH, viscosity, density, and solubility in some common solvents. The catalytic activity of new SAIL was demonstrated for the one-pot mechanosynthesis of pyrano[4,3-b]pyrans, dihydropyrano[3,2-c]chromene and tetrahydrobenzo[b]pyrans using planetary ball mill under solvent-free conditions. This current mechanosynthesis methodology for the synthesis of 4H-pyran-annulated heterocyclic scaffolds displays a combination of the synthetic virtues of conventional multi-component reaction with ecological benefits and convenience of a simple mechanocatalytic procedure. New SAIL was easily recycled and reused several times with no significant loss of activity.

Item Type: Article
Funders: UNSPECIFIED
Uncontrolled Keywords: Sulfonic acid-functionalized ionic liquid; Ball mill; Pyrano[4,3-b]pyran; Dihydropyrano[3,2-c]chromene; Tetrahydrobenzo[b]pyran; Metal and solvent-free conditions
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Nanotechnology & Catalysis Research Centre
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 22 Jan 2019 00:57
Last Modified: 22 Jan 2019 00:57
URI: http://eprints.um.edu.my/id/eprint/20067

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