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From the atom economy and environmentally friendly point of views, the development of clean and green approaches using ionic liquids (ILs) as recyclable catalysts has attracted increasing attention. The purpose of this study is to investigate the effect of task-specific ILs content on the one-pot three-component Biginelli reaction.

A series of halogen-free quaternary ammonium ILs functionalized with –SO₃H group were prepared and characterized by ¹H nuclear magnetic resonance (NMR), ¹³C NMR and electrospray ionization mass spectrometry. The ILs were used as catalysts for Biginelli reaction among aromatic aldehydes, urea or thiourea and β-dicarbonyl compounds. Anions and cations of ILs were varied to observe their effects on and contributions to the catalysts. The influencing factors, such as the amount of catalyst, solvent, reaction time and reaction temperature, were investigated.

The effect and contribution of cations of ILs were observed. Results showed that 3-(N, N-dimethylhexadecylammonium) propanesulfonic acid toluene sulfate ([DHPA][Tos]) showed comparable catalytic activity. Good adaptability to the reaction substrate and maximum product yield was observed when [DHPA][Tos] was used as catalyst. It was found that Biginelli reaction catalyzed by 10 mol% [DHPA][Tos] for 3 h under solvent-free conditions at 80 °C gave the best yield of 94%. Post-processing steps were simple, and the catalyst could be reused easily.

This paper demonstrates that ILs containing a long carbon chain and a bulky Tos anion efficiently promoted the reaction, in which the long carbon chains facilitate mass transfer in the reaction system.

Five halogen-free amphiphilic Brønsted acidic ionic liquids (ILs) based on 3-(N, N-dimethylalkylammonium)-propanesulphonate quaternary ammonium zwitterions and p-toluene sulphonic acid monohydrate were synthesized. The IL structures were characterized using ¹H NMR, ¹³C NMR and (ESI)-MS. The IL thermal instability was characterized using TG-DSC. The ILs were used as dual-solvent catalysts for esterification of several carboxylic acids, with different alcohols under mild conditions to study relevant structure-activity relationships. Results showed that the miscibility of the acidic IL, which is affected by the length of the carbon chain in the cation, is an important factor influencing the activity of the catalyst for the esterification reaction. Post-processing steps were simple, and the catalyst could be reused easily.