Phosphonium and Ammonium Ionic Liquids with Aromatic Anions: Synthesis, Properties, and Platinum Extraction

Several hydrophobic long-chain quaternary ammonium and phosphonium ionic liquids (ILs) with functionalized aromatic anions were prepared following a metathesis route using tricaprylmethylammonium chloride (Aliquat 336) and trihexyl(tetradecyl) phosphonium chloride (Cyphos IL101) as precursors. The incorporation of aromatic anions bearing hydroxy-, methoxy-, thiol-, and thioether functionalities as well as tetraphenylborate anions resulted in an increased chemical stability of the ILs and an alteration of their physico-chemical properties. Furthermore, aromatic anions significantly decreased the water solubility and water uptake of both ammonium and phosphonium-based ILs. Thiol- and thioether ILs were applied for the extraction of platinum from aqueous phase using liquid phase micro-extraction. Time dependent studies showed a rapid elimination of up to 95% platinum after 30 min. With a leaching of the anion <0.01 wt-% into the aqueous media, the evaluated ILs were found to be suitable as extracting agents for platinum from aqueous solutions.