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 deg 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.

Compounds

#	Formula	Name
1	C12H22F6N2O4S2	1-butyl-1-methylpiperidinium bis(trifluoromethanesulfonyl)imide
2	C11H20F6N2O4S2	1-methyl-1-propylpiperidinium bis(trifluoromethylsulfonyl)imide
3	C15H28F6N2O4S2	1-methyl-1-octylpyrrolidinium bis(trifluoromethylsulfonyl)amide
4	C13H24F6N2O4S2	1-hexyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide
5	C10H18F6N2O4S2	1-methyl-1-propylpyrrolidinium bis[(trifluoromethyl)sulfonyl]imide
6	C16H32F6N2O4S2	triethyloctylammonium bis[(trifluoromethyl)sulfonyl]imide
7	C15H30F6N2O4S2	tributylmethylammonium bis((trifluoromethyl)sulfonyl)imide
8	C12H24F6N2O4S2	butyltriethylammonium bis(trifluoromethylsulfonyl)imide
9	C10H20F6N2O5S2	N,N-diethyl-2-methoxy-N-methylethan-1-aminium bis((trifluoromethyl)sulfonyl)amide
10	C9H18F6N2O4S2	butyltrimethylammonium bis(trifluoromethylsulfonyl)imide
11	C9H18F6N2O4S2	N-ethyl-N,N-dimethyl-1-propanaminium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
12	CCl4	tetrachloromethane
13	CHBr3	tribromomethane

Datasets

The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type	Compound-#	Property	Variable	Constraint	Phase	Method	#Points
POMD	12 6	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 7	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 8	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 9	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 11	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 10	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 1	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 2	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 3	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 4	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	12 5	Mass fraction - 12 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 6	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 7	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 8	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 9	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 11	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 10	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 1	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 2	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 3	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 4	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3
POMD	13 5	Mass fraction - 13 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Chromatography	3

Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

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

AlSaleem, S. S.[Saleem S.], Zahed, W. M.[Waleed M.], Alnashef, I. M.[Inas M.], Hadj-Kali, M. K.[Mohamed K.]

ABSTRACT