Double salt ionic liquids prepared by mixing partially miscible ionic liquids: Tuning the solubility of lipophilic molecules

• Author(s): Wang, Hui ; Pereira, Jorge F.B. [UNESP] ; Myerson, Allan S. ; Rogers, Robin D.
• Date: 2018
• Persistent ID: http://hdl.handle.net/11449/167747
• Origin: Oasisbr
• Document Type: Other
• Language: English

Description

Made available in DSpace on 2018-12-11T16:38:10Z (GMT). No. of bitstreams: 0 Previous issue date: 2014-01-01

Massachusetts Institute of Technology

Double Salt Ionic Liquids (DSILs) were prepared by mixing 1- ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C2mim][NTf2]) and trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide ([P66614][NTf2]) in their miscible range: [C2mim]x[P66614](1-x)[NTf2] (0 ≤ x ≤ 0.29). ¹H NMR, ¹⁹F NMR, and FT-IR spectroscopic studies indicated that the [NTf2]- anions preferentially interact with the [C2mim]⁺ cations. Solubility studies showed that solutes with long alkyl chains (e.g., heptane, methyl palmitate), which have good solubility in [P66614][NTf2] but are not totally miscible, have tunable solubility in the DSILs and the presence of even minor amounts of [C2mim]⁺ significantly decreases their solubility. However, the solubilities of benzene, toluene, 1-octanol, and poly(ethylene glycol) (PEG-300) in [C2mim]x[P66614]^(1-x)[NTf2] were controlled by their miscibility with [P66614][NTf2], and can't be tuned by changing the ion concentrations within the miscibility range.

Department of Chemistry, Center for Green Manufacturing, University of Alabama

Department of Chemical Engineering, Novartis-MIT Center for Continuous Manufacturing, Massachusetts Institute of Technology, 77 Massachusetts Avenue

Department of Bioprocess and Biotechnology, School of Pharmaceutical Sciences, UNESP - Universidade Estadual Paulista

Department of Bioprocess and Biotechnology, School of Pharmaceutical Sciences, UNESP - Universidade Estadual Paulista