Mutual Solubility of Aromatic Hydrocarbons in Pyrrolidinium and Ammonium-Based Ionic Liquids and Its Modeling Using the Cubic-Plus-Association (CPA) Equation of State

Abstract

In this work, the mutual solubility of 30 binary systems {aromatic hydrocarbon (1) + ionic liquid (2)} involving benzene, toluene, ethylbenzene, o-xylene, m-xylene, and p-xylene as aromatics and the ionic liquids, 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyland tributylmethylammonium bis(trifluoromethylsulfonyl)imide, [N 4441 ][NTf 2 ], were determined in the temperature range of T = (293.15 to 333.15) K at p = 0.1 MPa. The influence of the temperature and the structural characteristics of the aromatic hydrocarbons as well as the effect of the structure of the ionic liquids on the phase behavior was analyzed. A comparison between the experimental LLE of the binary systems presented in this work and those found in literature was also carried out. Finally, all the binary systems were satisfactorily modeled using the Cubic-Plus-Association (CPA) Equation of State (EoS).

Chloroaluminate Liquid Clathrates: Is It the Cations or the Anions That Drive the Solubility of Aromatics?

“…The molar solubility of the aromatics was calculated from the integral ratio of the aromatic protons and the methyl protons of each IL. , The trend in aromatic solubilities was the same in all three ILs: benzene > toluene > o -xylene > p -xylene ∼ m -xylene > mesitylene (Figure ). This is the same trend observed in other LC systems published in the literature. , Here, we observe a marked difference in the solubility of mesitylene, which is 50–80% lower than benzene in all three ILs. It is unclear whether this trend is a result of electronic or steric effects.…”

“…Our study of the solubilities of a range of aromatic solvents in [HN 222 ]­[Al 2 Cl 7 ], [N 2222 ]­[Al 2 Cl 7 ], and [HN 222 ]­[AlCl 4 ] IL-based LCs, and the subsequent crystallographic and spectroscopic characterization, revealed interesting trends which suggest specific cation/aromatic interactions and anion speciation. The molar solubilities of the aromatic solvents in all three ILs were found to be benzene > toluene > o -xylene > p -xylene ∼ m -xylene > mesitylene, in agreement with the literature; , however, the solubilities in the [AlCl 4 ] − IL were 40–70% lower than those found for the two [Al 2 Cl 7 ] − ILs, which were nearly equivalent. Attempts to crystallize solvates of the aromatics from the six [N 2222 ]­[Al 2 Cl 7 ]/aromatic LCs led to the formation of crystals of [N 2222 ]­[Al 2 Cl 7 ]·C 6 H 6 from benzene but only to crystals of [N 2222 ]­[AlCl 4 ] from the other five aromatic systems, indicating disproportionation of the anion.…”

“…This is the same trend observed in other LC systems published in the literature. 30,31 Here, we observe a marked difference in the solubility of mesitylene, which is 50−80% lower than benzene in all three ILs. It is unclear whether this trend is a result of electronic or steric effects.…”

Solubility of Xylene Isomers in Seven Deep Eutectic Solvents

“…The increase in the chain length rendered the HBDs less polar and enhanced the interactions of the DESs with xylenes. Furthermore, the entropic effect caused by the increase in the chain length contributed to the solubility enhancement …”

Impact of the Cationic Moiety of Ionic Liquids on Chemoselective Artificial Olfaction

“…Overall, all sensor responses were reversible, exhibiting an upward trend upon gas analyte exposure, as well as a faster (<1 s) response profile to the tested volatiles (Figure 4a) when compared to other liquid crystal-based sensing geometries reported in the literature (response times between 1 and 200 s). [23][24][25]29 The cycle signal shape was stable up to the maximum tested storage time of 1 week. Because of this stability, it was possible to use signals yielded by the hybrid material sensor with different storage times to successfully implement the machine-learning algorithm.…”