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

New Series of Green Cyclic Ammonium-Based Room Temperature Ionic Liquids with Alkylphosphite-Containing Anion: Synthesis and Physicochemical Characterization

Zarrougui, R.[Ramzi], Raouafi, N.[Noureddine], Lemordant, D.[Daniel]
J. Chem. Eng. Data 2014, 59, 4, 1193-1201
ABSTRACT
A new series of 12 cyclic ammonium-based room temperature ionic liquids (RTILs) containing an alkylphosphite anion have been synthesized by an alkylation reaction between cyclic tertiary amines and dialkylphosphite. This method constitutes an eco-friendly pathway to RTILs that does not generate any secondary byproducts and avoiding the metathesis reaction involving uses of nonfriendly or expensive salts. Their physicochemical and electrochemical properties have been investigated. The temperature dependency of density, dynamic viscosity, and ionic conductivity were determined at temperatures varying from 293.15 to 323.15 K and were discussed on a structural basis. For the prepared RTILs, the viscosity values are fairly high and low ionic conductivity as compared to usual ILs. The transport properties were found to be temperature-dependent and followed the Arrhenius law. The RTILs potential windows (?E) are comprised between 3.00 and 4.77 V. The electrochemical stability seems to be influenced by the alkyl side chain. An increasing in the carbon number of the cation and anion side chain decreases the electrochemical window of RTILs. The correlation between ionic conductivity and viscosity was studied on the basis of the Walden rule, and the new RTILs can be classified as associated ionic liquids (AILs), an intermediate between a true, ionic liquid and a molecular species.
Compounds
# Formula Name
1 C9H22NO3P N-ethyl-N-methylpyrrolidinium ethylphosphonate
2 C9H22NO4P 4-ethyl-4-methylmorpholin-4-ium ethylphosphonate
3 C10H24NO3P 1-ethyl-1-methylpiperidin-1-ium ethyl phosphonate
4 C13H30NO3P 1-butyl-1-methylpyrrolidin-1-ium butyl phosphonate
5 C13H30NO4P 4-butyl-4-methylmorpholin-4-ium butylphosphonate
6 C14H32NO3P 1-butyl-1-methylpiperidin-1-ium butyl phosphonate
7 C17H38NO3P N-hexyl-N-methylpyrrolidinium hexylphosphonate
8 C17H38NO4P 4-hexyl-4-methylmorpholin-4-ium hexylphosphonate
9 C18H40NO3P 1-hexyl-1-methylpiperidin-1-ium hexylphosphonate
10 C21H46NO3P N-methyl-N-octylpyrrolidinium octylphosphonate
11 C21H46NO4P 4-methyl-4-octylmorpholin-4-ium octylphosphonate
12 C22H48NO3P 1-methyl-1-octylpiperidin-1-ium octyl phosphonate
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
  • Vibrating tube method
  • 13
  • POMD
  • 1
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 1
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 2
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 2
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 2
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 3
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 3
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 3
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 4
  • 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
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 4
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 5
  • 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
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 5
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 6
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 6
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:8
  • 13
  • POMD
  • 6
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 7
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 7
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 7
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 8
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 8
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 8
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 9
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 9
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 9
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 10
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 10
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 10
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 11
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 11
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 11
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13
  • POMD
  • 12
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 13
  • POMD
  • 12
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CONPLT:UFactor:4
  • 13
  • POMD
  • 12
  • Electrical conductivity, S/m ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Alternating current cell with electrodes
  • 13