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

Synthesis and Physical Properties of Choline Carboxylate Ionic Liquids

Muhammad, N.[Nawshad], Hossain, M. I., Man, Z.[Zakaria], El-Harbawi, M.[Mohanad], Bustam, M. A.[M. Azmi], Noaman, Y. A.[Yousr Abdulhadi], Alitheen, N. B. M.[Noorjahan Banu Mohamed], Ng, M. K.[Mei Kee], Hefter, G.[Glenn], Yin, C.-Y.[Chun-Yang]
J. Chem. Eng. Data 2012, 57, 8, 2191-2196
ABSTRACT
A series of choline carboxylate ionic liquids (ILs) have been synthesized by neutralization of choline hydroxide solution with acetic, propanoic, butanoic, pivalic, and hexanoic acids. The salts so obtained were characterized by NMR spectroscopy, thermal methods, and elemental analysis. Key physical properties (density, viscosity, and refractive index) were measured for the propanoate, butanoate, and hexanoate salts at temperatures from (293.15 to 353.15) K. The densities were used to estimate the molecular volumes, standard entropies, crystal lattice energies, and thermal expansion coefficients. All five choline carboxylates were found to have cytotoxicities (IC50 values) above 10 mM toward the human breast cancer cell line, MCF-7, indicating they are much less toxic than common imidazolium-based ILs.
Compounds
# Formula Name
1 C7H16NO2 2-acetoxy-N,N,N-trimethylethanaminium
2 C10H23NO3 choline pivalate
3 C8H19NO3 cholinium propanoate
4 C9H21NO3 choline butanoate
5 C11H25NO3 2-hydroxy-N,N,N-trimethylethanaminium hexanoate
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
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • AC calorimetry
  • 1
  • POMD
  • 2
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • AC calorimetry
  • 1
  • POMD
  • 3
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONCYL:UFactor:2
  • 13
  • POMD
  • 3
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 9
  • POMD
  • 3
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 4
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONCYL:UFactor:2
  • 13
  • POMD
  • 4
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 9
  • POMD
  • 4
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 5
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONCYL:UFactor:2
  • 13
  • POMD
  • 5
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 9
  • POMD
  • 5
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13