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

Solubilities of Cinnamic Acid Esters in Ionic Liquids

Panteli, E. K.[Eleni K.], Voutsas, E. C.[Epaminondas C.]
J. Chem. Eng. Data 2009, 54, 3, 812-818
ABSTRACT
The solubilities of three cinnamic acid esters, namely, methyl ferulate, methyl p-coumarate, and methyl sinapate, in eight imidazolium-based ionic liquids composed of the PF6 - and BF4 - anions have been measured at (30, 39, and 48) deg C. Higher solubilities of the three esters were observed in the ionic liquids composed of the BF4 - anion than those composed of the PF6 - anion. Also, higher solubilities are observed in alkylsubstituted (on the imidazolium cation moiety) ILs than in polar-substituted ILs, whereas, as the alkyl chain length on the cation moiety increases, the solubility increases as well. Moreover, using the van t Hoff equations, the apparent Gibbs energy, enthalpy, and entropy of solution were calculated. Positive values of the three thermodynamic functions were found in all cases. Finally, successful correlations of the experimental data were achieved with the UNIQUAC and the NRTL activity coefficient models.
Compounds
# Formula Name
1 C10H10O3 2-propenoic acid, 3-(4-hydroxyphenyl)-, methyl ester
2 C11H12O4 methyl 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
3 C12H14O5 3,5-dimethoxy-4-hydroxy cinnamic acid methyl ester
4 C8H15F6N2P 1-butyl-3-methylimidazolium hexafluorophosphate
5 C12H23F6N2P 1-octyl-3-methylimidazolium hexafluorophosphate
6 C6H11F6N2OP 3-(2-hydroxyethyl)-1-methylimidazolium hexafluorophosphate
7 C7H13F6N2OP 1-(2-methoxyethyl)-3-methyl-imidazolium hexafluorophosphate
8 C8H15BF4N2 1-butyl-3-methylimidazolium tetrafluoroborate
9 C12H23BF4N2 1-methyl-3-octylimidazolium tetrafluoroborate
10 C6H11BF4N2O 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate
11 C7H13BF4N2O 1-(2-methoxyethyl)-3-methyl-imidazolium tetrafluoroborate
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
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 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
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • 9
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 1
  • 10
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 1
  • 11
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 2
  • 5
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 2
  • 6
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 2
  • 7
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 2
  • 8
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 2
  • 9
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 2
  • 10
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 2
  • 11
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 3
  • 5
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 3
  • 6
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 3
  • 7
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 3
  • 8
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 3
  • 9
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 3
  • 10
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 3
  • 11
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 1
  • 4
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 2
  • 4
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • Chromatography
  • 3
  • POMD
  • 3
  • 4
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 3
  • POMD
  • 1
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 1
  • 7
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 1
  • 8
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3