ABSTRACT

Binary liquid-liquid equilibria in mixtures of fluorinated benzenes and ionic liquid, 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([emim][Tf2N]), have been measured using the volumetric method over a temperature range from about (283 to 373) K. A general trend between the magnitude of the dipole moment (polarity) and the miscibility was found, although other intermolecular interactions (higher-order moments, o-electron effects, and hydrogen bonding) may also be playing a role for a more detailed trend. The fluorinated benzenes having the largest dipole moments (1,2-difluorobenzene, 1,2,3,4-tetrafluorobenzene, and 1,2,3-trifluorobenzene) were completely miscible in the [emim][Tf2N]. The binary systems (1,4- difluorobenzene, 1,3,5-trifluorobenzene, and 1,2,4,5-tetrafluorobenzene) with zero dipole moments, and the binary systems (1,2,4-trifluorobenzene, fluorobenzene, 1,3-difluorobenzene, pentafluorobenzene, and 1,2,3,5- tetrafluorobenzene) with dipole moments of about 1.4 D were only partially miscible in [emim][Tf2N] (immiscibility gaps from about (11 to 50) mol % in [emim][Tf2N]). The binary system (1,2,4-trifluorobenzene + [emim][Tf2N]) shows a lower critical solution temperature (LCST) of about 354 K. The excess molar volumes range from (-1 to -10) cm3 * mol-1. Observed LLE are well correlated by use of the nonrandom two liquid (NRTL) solution model.

Compounds

#	Formula	Name
1	C6H5F	fluorobenzene
2	C6H4F2	1,2-difluorobenzene
3	C6H4F2	1,3-difluorobenzene
4	C6H4F2	1,4-difluorobenzene
5	C6H3F3	1,2,3-trifluorobenzene
6	C6H3F3	1,2,4-trifluorobenzene
7	C6H3F3	1,3,5-trifluorobenzene
8	C6H2F4	1,2,3,4-tetrafluorobenzene
9	C6H2F4	1,2,3,5-tetrafluorobenzene
10	C6H2F4	1,2,4,5-tetrafluorobenzene
11	C6HF5	pentafluorobenzene
12	C8H11F6N3O4S2	1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide

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	1	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	2	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	3	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	4	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	5	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	6	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	7	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	8	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	9	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	10	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	11	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Pycnometric method	2
POMD	1 12	Mole fraction - 1 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	1 12	Mole fraction - 1 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	1 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 1; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	1 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2 Mole fraction - 1; Liquid mixture 2		Liquid mixture 2 Liquid mixture 1	Pycnometric method	6
POMD	3 12	Mole fraction - 3 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	3 12	Mole fraction - 3 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	3 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 3; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	3 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2	Mole fraction - 3; Liquid mixture 2	Liquid mixture 2 Liquid mixture 1	Pycnometric method	6
POMD	4 12	Mole fraction - 4 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	4 12	Mole fraction - 4 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	4 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 4; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	4 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2 Mole fraction - 4; Liquid mixture 2		Liquid mixture 2 Liquid mixture 1	Pycnometric method	6
POMD	6 12	Mole fraction - 6 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	3
POMD	6 12	Mole fraction - 6 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	3
POMD	6 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 6; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	3
POMD	6 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2	Mole fraction - 6; Liquid mixture 2	Liquid mixture 2 Liquid mixture 1	Pycnometric method	3
POMD	7 12	Mole fraction - 7 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	7 12	Mole fraction - 7 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	7 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 7; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	7 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2	Mole fraction - 7; Liquid mixture 2	Liquid mixture 2 Liquid mixture 1	Pycnometric method	6
POMD	9 12	Mole fraction - 9 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	9 12	Mole fraction - 9 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	9 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 9; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	9 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2	Mole fraction - 9; Liquid mixture 2	Liquid mixture 2 Liquid mixture 1	Pycnometric method	6
POMD	10 12	Mole fraction - 10 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	10 12	Mole fraction - 10 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	10 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 10; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	10 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2 Mole fraction - 10; Liquid mixture 2		Liquid mixture 2 Liquid mixture 1	Pycnometric method	6
POMD	11 12	Mole fraction - 11 ; Liquid mixture 1	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	volumetric method	6
POMD	11 12	Mole fraction - 11 ; Liquid mixture 2	Temperature, K; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 2 Liquid mixture 1	volumetric method	6
POMD	11 12	Molar volume, m3/mol ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Mole fraction - 11; Liquid mixture 1		Liquid mixture 1 Liquid mixture 2	Pycnometric method	6
POMD	11 12	Molar volume, m3/mol ; Liquid mixture 2	Temperature, K; Liquid mixture 2 Mole fraction - 11; Liquid mixture 2		Liquid mixture 2 Liquid mixture 1	Pycnometric method	6

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

Liquid-Liquid Equilibria in Binary Mixtures Containing Fluorinated Benzenes and Ionic Liquid 1-Ethyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide

Shiflett, M. B.[Mark B.], Yokozeki, A.

ABSTRACT