Ionic liquid-functionalized silica for selective solid-phase extraction of organic acids, amines and aldehydes

Abstract

Three ionic liquid (IL)-functionalized silica materials, imidazolium, N-methylimidazolium and 1-alkyl-3-(propyl-3-sulfonate) imidazolium, were synthesised and applied in solid-phase extraction (SPE) of organic acids, amines and aldehydes, which are important compound families in atmospheric aerosol particles. 1-Alkyl-3-(propyl-3-sulfonate) imidazolium-functionalized silica was tested as sorbent for SPE for the first time. The analytes were separated and detected by liquid chromatography–mass spectrometry (LC–MS). To confirm the results achieved by LC–MS, the acids were additionally determined by gas chromatography–mass spectrometry (GC–MS). The stability of the IL-functionalized silica materials was tested at low and high pH. The effect of the pH on the extraction was also informative of the retention mechanism of the materials. The results showed anion exchange to be the main interaction, but hydrophobic and π interactions and hydrogen bonding also played a role in the extraction. Extraction efficiencies for organic acids ranged from 87 to 110%, except for cis-pinonic acid (19–29%). Lower extraction efficiencies for amines and aldehydes confirmed that anionic exchange was the predominant interaction. Comparisons made with two commercial SPE materials—silica-based strong anion exchange (SAX) and polymer-based mixed-mode anion exchange and reverse-phase (MAX)—showed the IL-functionalized materials to offer different selectivity and better extraction efficiency than SAX for aromatic compounds. Finally, the new materials were successfully tested in the extraction of an atmospheric aerosol sample.