An efficient and facile synthesis of the coumarin and ester derivatives using sulfonated polyionic liquid as a highly active heterogeneous catalyst

Document Type : Research Article


Payame Noor University


Article history:
Received in revised form
Available online In this research, a novel solid acid catalyst, sulfonic acid immobilized on poly ionic liquid (SPIL), was described. The final catalyst, SPIL, which was simply synthesized and characterized by fourier transform infrared spectroscopy and thermo‐gravimetric analysis, was found to be an efficient and environmentally benign solid acid for the Pechmann and esterification reactions under the solvent free conditions. The studies showed that the catalyst could be easily recovered and reused at least three reaction cycles without any significant loss in catalytic activity and efficiency.
1. Introduction

Ionic liquids, a class of low-melting chemical compounds that include an organic cation and an organic/inorganic anion, are known as molten salts. Generally, the cation is an organic species containing heteroatoms such as phosphorous, sulfur, and nitrogen and the anion may be varied as chloride, bromide, iodide, tetrafluoroborate, hexafluorophosphate, nitrate, and acetate [1]. Because of their unique properties such as non-volatility, non-flammability, safety, recyclability and ability to dissolve a wide range of compounds, a variety of ionic liquids have been used in organic synthesis [2-6].In recent years, synthesis of

Graphical Abstract

An efficient and facile synthesis of the coumarin and ester derivatives using sulfonated polyionic liquid as a highly active heterogeneous catalyst


[1] J. Dupont, R. F. de Souza, P. A. Suarez, Ionic Liquid (Molten Salt) Phase Organometallic Catalysis, Chem. Rev., 102 (2002) 3667-3692.
[2] H. Olivier-Bourbigou, L. Magna, D. Morvan, Ionic liquids and catalysis: Recent progress from knowledge to applications. App. Catal. A., 373 (2010) 1-56.
[3] C. Hardacre, V. Parvulescu, catalysis in ionic liquids from catalyst synthesis to application Catalysis in Ionic Liquids, RSC Catalysis Series (2014).
[4] H. Ohno, Design of ion conductive polymers based on ionic liquids Electrochemical Aspects of Ionic Liquids, WileyVCH, Weinheim (2005).
[5] C. Petra, B. Katalin, Application of Ionic Liquids in Membrane Separation Processes, Ionic Liquids: Applications and Perspectives, Intech (2011).
[6] H. M. Marwani, E. Bakhsh, Silica Gel Supported Hydrophobic Ionic Liquid for Selective Extraction and Determination of Coumarin, Am. J. Anal. Chem., 4 (2013) 8-16.
[7] J. B. Tang, H. D. Tang, W. L. Sun, H. Plancher, M. Radosz, Y. Shen, A thermoreversible ion gel by triblock copolymer self-assembly in an ionic liquid, Chem. Commun., 26 (2007) 2732-2734.
[8] R. T. Carlin, J. Fuller, Lyotropic liquid-crystalline gel formation in a room-temperature ionic liquid, Langmuir., 18 (2002) 7258-7260.
[9] T. Sato, S. Marukane, T. Narutomi, T. J. Akao, Poly (ionic liquid) s as optically transparent microwave-absorbing materials. Macromol., 41 (2008) 493-496.
[10] N. Matsumi, K. Sugai, M. Miyake, H. Ohno, Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities. Macromol., 212 (2011) 2522-2528.
[11] D. E. Vos, I. F. K. Vankelecom, P. A. Jacobs, An easily recoverable and efficient catalyst for heterogeneous cyclopropanation of olefins Chiral Catalyst Immobilization and Recycling, Wiley–VCH: Weinheim (2000).
[12] A. Shaabani, A. Rahmati, Z. Badri, Starch Immobilized Ruthenium Trichlorid Catalyzed Oxidative Cyanation of Tertiary Amines with Hydrogen Peroxide, Chem. Cat. Chem., 3 (2011) 1329-1332.
[13] J. P. Lourenço, M. I. Macedo, A. Fernandes, Regulation of Pore Structure and Acidity on ZSM-5 Catalyst for Dehydration of Glycerol to Acrolein, Acta. Phys. Chem. Sin., 31 (2015) 965-972.
[14] Y. Leng, P. Jiang, J. Wang, A novel Brønsted acidic heteropolyanion-based polymeric hybrid catalyst for esterification. Catal. Commun., 25 (2012) 41-44.
[15] S. Shylesh, V. Nemann, W. R. Thiel, Magnetically Separable Nanocatalysts: Bridges between Homogeneous and Heterogeneous Catalysis. Angew. Chem., Int. Ed., 49 (2010) 3428-3459.
[16] P. Wasserscheid, W. Keim, Reversible physical absorption of SO 2 by ionic liquids. Angew. Chem. Int. Ed., 39 (2000) 3772-3789.
[17] P. T. Anastas, M. Kirchhoff, A recyclable electrochemical allylation in water. Acc. Chem. Res., 35 (2002) 686-694.
[18] M. C. Burleigh, M. A. Markowitz, M. S. Spector, B. Gaber, Organosilica copolymers for the adsorption and separation of multiple pollutants. J. Phys. Chem. B., 109 (2005) 9198-9201.
[19] A. Bordoloi, S. Sahoo, F. Lefebvre, S. B. J. Halligudi, Selective oxidation of benzyl alcohol by two phase electrolysis using nitrate as mediator. Catal. Sci. Technol. 2 (2012) 824-827.
[20] D. Margolese, J. A. Melero, S. C. Christiansen, B. Chmelka, G. D. Stucky, Direct observation of nanorange ordered microporosity within mesoporous molecular sieves, Chem. Mater., 12 (2000) 2448-2459