Solubility of Halogenated Hydrocarbons in Hydrophobic Ionic Liquids: Experimental Study and COSMO-RS Prediction

Abstract

Halogenated hydrocarbons are members of priority water contaminants because of their negative health and environmental impacts. In this study, the solubility of three halogenated hydrocarbons, namely, carbon tetrachloride, chloroform, and bromoform was measured in 12 hydrophobic ionic liquids (ILs) for temperature ranging between 25 and 45 °C. We investigated the chemical structure and alkyl chain length effect of three different cations (piperidinium, pyrrolidinium, and ammonium-based) paired with bis­(trifluoromethylsulfonyl)­imide anion. It was found that carbon tetrachloride and bromoform are partially miscible in all tested ILs while chloroform exhibits full miscibility. For ammonium based ionic liquids, the solubility increases with the increase of the cation molecular weight and alkyl chain length. The results indicate that the solubility of the studied halogenated hydrocarbons in methyltrioctylammonium bis­(trifluoromethylsulfonyl)­imide, octyltriethylammonium bis­(trifluoromethylsulfonyl)­imide, and 1-octyl-1-methylpyrrolidinium bis­(trifluoromethylsulfonyl)-imide is substantial. These results confirm the potential use of ionic liquids as powerful alternative solvents for wastewater treatment. Finally, the predictive capability of COSMO-RS model provided excellent qualitative agreement with experimental data both for temperature dependence and for cations structure effect.

Screening of Ionic Liquids for Keratin Dissolution by Means of COSMO-RS and Experimental Verification

“…20 It has also attracted a significant amount of attention in terms of ILs, as it integrates the dominant interaction forces of H-bonds, misfits and van der Waals in ILs systems. [21][22] Many results on the prediction of polymer properties in ILs have been reported, and it is obvious that calculating the activity coefficients, 23 solubility coefficients 1,24 and excess enthalpy 25 of polymer in ILs is an effective way of evaluating the dissolution ability of the ILs. Casas et al, 26 for instance, found that the solubility of cellulose and lignin could be accurately predicted by using activity coefficients and excess enthalpy via COSMO-RS.…”

“…COSMO-RS, a well-defined method for predicting the thermophysical properties of liquids, is a useful tool for predicting the solubility of polymers through the hypothesis that polymers can be treated as solutions consisting of monomers or oligomers with a small number of repeat units . It has also attracted a significant amount of attention in terms of ILs, as it integrates the dominant interaction forces of H bonds, misfits, and van der Waals in ILs systems. , Many results on the prediction of polymer properties in ILs have been reported, and it is obvious that calculating the activity coefficients, solubility coefficients, , and excess enthalpy of polymer in ILs is an effective way of evaluating the dissolution ability of the ILs. Casas et al, for instance, found that the solubility of cellulose and lignin could be accurately predicted by using activity coefficients and excess enthalpy via COSMO-RS.…”

Solubility of Monomers for Chain Polymerization in Ionic Liquids Predicted by the Conductor-Like Screening Model for Real Solvents

“…The prediction errors can probably be attributed to the weak interactions in p -MeSt–IL systems; however, this does not affect the predicted trend. COSMO-RS is thus a suitable tool for ranking ILs qualitatively in terms of the solubilities of vinyl monomers in ILs …”

“…COSMO-RS is thus a suitable tool for ranking ILs qualitatively in terms of the solubilities of vinyl monomers in ILs. 38 3.2. Solubilities of p-MeSt and IBVE in ILs.…”

Solubility of gaseous hydrocarbons in ionic liquids using equations of state and machine learning approaches

“…The nitrogen analyzer was used to measure the solubilities of five typical ILs in the examined hydrocarbons, revealing COSMO-RS's adequate capacity to forecast IL-in-hydrocarbon solubilities. AlSaleem 16 investigated the solubility of three halogenated hydrocarbons in 12 hydrophobic ILs at temperatures ranging from 25 to 45 °C. Piperidinium, pyrrolidinium, and ammonium-based cations coupled with [TF 2 N] anion were studied for their chemical structure and alkyl chain length impact.…”