ABSTRACT

Hydrophobic ionic liquids containing 1-butyl-2,3-dimethylpyridinium [B2M3MPYR], 1-butyl-3,5-dimethylpyridinium [B3M5MPYR], 1-butyl-2-methyl-5-ethylpyridinium [B2M5EPYR], 1-butyl-2,3,5-trimethylpyridinium [B2M3M5MPYR], 1-octyl-2,3-dimethylpyridinium [O2M3MPYR], 1-octyl-3,5-dimethylpyridinium [O3M5MPYR], 1-octyl-2-methyl-5-ethylpyridinium [O2M5EPYR], or 1-octyl-2,3,5-trimethylpyridinium [O2M3M5MPYR] as the cation and bis(trifluoromethanesulfonyl)imide [NTf2], trifluoromethanesulfonate [TfO], dicyanamide [N(CN)2], thiocyanate [SCN] or iodide as the anion have been synthesized, and their physicochemial properties have been studied. Thermal properties, solubilities in water and water contents, UV-vis spectra, densities, refractive indices, electrochemical windows, and toxicities on Vibrio fischeri have been measured. These ionic liquids, most of which are liquid at room temperature, exhibit high refractive indices and increased hydrophobicity. Despite high toxicity values toward V. fischeri, ionic liquids containing a dialkylpyridinium or trialkylpyridinium cation with an octyl chain represent good alternatives to extracting solvents.

Compounds

#	Formula	Name
1	C15H26IN	3,5-dimethyl-1-octylpyridinium iodide
2	C16H28IN	5-ethyl-2-methyl-1-octylpyridinium iodide
3	C16H28IN	2,3,5-trimethyl-1-octylpyridinium iodide
4	C13H18F6N2O4S2	1-butyl-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)amide
5	C13H18F6N2O4S2	1-butyl-2,3-dimethylpyridinium bis(trifluoromethylsulfonyl)amide
6	C14H20F6N2O4S2	1-butyl-5-ethyl-2-methylpyridinium bis(trifluoromethylsulfonyl)amide
7	C14H20F6N2O4S2	1-butyl-2,3,5-trimethylpyridinium bis(trifluoromethylsulfonyl)amide
8	C17H26F6N2O4S2	3,5-dimethyl-1-octylpyridinium bis(trifluoromethylsulfonyl)amide
9	C17H26F6N2O4S2	2,3-dimethyl-1-octylpyridinium bis(trifluoromethylsulfonyl)amide
10	C18H28F6N2O4S2	5-ethyl-2-methyl-1-octylpyridinium bis(trifluoromethylsulfonyl)amide
11	C18H28F6N2O4S2	2,3,5-trimethyl-1-octylpyridinium bis(trifluoromethylsulfonyl)amide
12	C12H18F3NO3S	1-butyl-3,5-dimethylpyridinium 1,1,1-trifluoromethanesulfonate
13	C12H18F3NO3S	1-butyl-2,3-dimethylpyridinium 1,1,1-trifluoromethanesulfonate
14	C13H20F3NO3S	1-butyl-2,3,5-trimethylpyridinium 1,1,1-trifluoromethanesulfonate
15	C16H26F3NO3S	3,5-dimethyl-1-octylpyridinium 1,1,1-trifluoromethanesulfonate
16	C16H26F3NO3S	2,3-dimethyl-1-octylpyridinium 1,1,1-trifluoromethanesulfonate
17	C17H28F3NO3S	2,3,5-trimethyl-1-octylpyridinium 1,1,1-trifluoromethanesulfonate
18	C13H18N4	1-butyl-3,5-dimethylpyridinium dicyanamide
19	C13H18N4	1-butyl-2,3-dimethylpyridinium dicyanamide
20	C17H26N4	3,5-dimethyl-1-octylpyridinium dicyanamide
21	C18H28N4	5-ethyl-2-methyl-1-octylpyridinium dicyanamide
22	C12H18N2S	1-butyl-3,5-dimethylpyridinium thiocyanate
23	C16H26N2S	3,5-dimethyl-1-octylpyridinium thiocyanate
24	C16H26N2S	2,3-dimethyl-1-octylpyridinium thiocyanate
25	C17H28N2S	2,3,5-trimethyl-1-octylpyridinium thiocyanate
26	C15H26BF4N	3,5-dimethyl-1-octylpyridinium tetrafluoroborate
27	H2O	water

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	Phase	Method	#Points
POMD	1	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	1	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	1	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	2	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	2	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	2	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	3	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	3	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	4	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	4	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	4	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	5	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	5	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	5	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	6	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	6	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	6	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	7	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	7	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	7	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	8	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	8	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	8	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	9	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	9	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	9	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	10	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	10	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	11	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	11	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	11	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	12	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	12	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	12	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	13	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	13	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	13	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	13	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	13	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	14	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	14	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	15	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	15	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	16	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	16	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	16	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	17	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	18	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	18	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	18	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	18	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	19	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	19	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	20	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	20	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	20	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	21	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	21	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	22	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	22	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	22	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	23	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	23	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	23	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	23	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	23	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	24	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	24	Refractive index (Na D-line) ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Standard Abbe refractometry	1
POMD	24	Mass density, kg/m3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid	Liquid	Pycnometric method	1
POMD	25	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	25	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DTA	1
POMD	25	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	26	Molar enthalpy of transition or fusion, kJ/mol ; Crystal		Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	26	Normal melting temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	27 2	Mass fraction - 2 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 3	Mass fraction - 3 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 4	Mass fraction - 4 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 5	Mass fraction - 5 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 6	Mass fraction - 6 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 7	Mass fraction - 7 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 8	Mass fraction - 8 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 9	Mass fraction - 9 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 10	Mass fraction - 10 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 16	Mass fraction - 16 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 15	Mass fraction - 15 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 17	Mass fraction - 17 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 20	Mass fraction - 20 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 21	Mass fraction - 21 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 23	Mass fraction - 23 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1
POMD	27 24	Mass fraction - 24 ; Liquid mixture 1	Temperature, K; Liquid mixture 1 Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid mixture 2	Beer-Lambert's law	1

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

Synthesis, Physicochemical Properties, and Toxicity Data of New Hydrophobic Ionic Liquids Containing Dimethylpyridinium and Trimethylpyridinium Cations

Papaiconomou, N.[Nicolas], Estager, J.[Julien], Traore, Y.[Youssouf], Bauduin, P.[Pierre], Bas, C.[Corine], Legeai, S.[Sophie], Viboud, S.[Sylvie], Draye, M.[Micheline]

ABSTRACT