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

New Highly CO2-Philic Diglycolic Acid Esters: Synthesis and Solubility in Supercritical Carbon Dioxide

Yang, H.-J.[Hai-Jian], Tian, J.[Jia], Kim, H.[Hakwon]
J. Chem. Eng. Data 2010, 55, 10, 4130-4139
ABSTRACT
A series of diglycolic acid esters, potent CO2-philic chelating agents, were designed and synthesized. The solubilities of these compounds in supercritical CO2 were determined at temperatures from (313 to 333) K and pressures from (8.6 to 20.4) MPa. All of the synthesized esters showed good to high solubility (as high as 1.6*10-2 mol*L-1 for compound 1 at 9.3 MPa and 313 K) in supercritical CO2 at easily accessible temperatures and pressures. To confirm the tested solubility, two density-based correlations proposed by Bartle and Chrastil were investigated for the seven glycolic acid esters.The results showed good self-consistency of the data calculated by the Bartle semiempirical equation and differed from the measured values by between (4 and 37) %. Better agreement with experimental solubility data is obtained with the Chrastil model, and values of AARD lower than 11 % were observed. Solubility data were also used to estimate the partial molar volume 2 for each diglycolic acid ester in the supercritical phase using the theory developed by Kumar and Johnston.
Compounds
# Formula Name
1 C12H22O5 dibutyl 2,2'-oxydiacetate
2 C16H30O5 dihexyl 2,2'-oxydiacetate
3 C20H38O5 dioctyl 2,2'-oxydiacetate
4 C24H46O5 didecyl 2,2'-oxydiacetate
5 C28H54O5 didodecyl 2,2'-oxydiacetate
6 C32H62O5 ditetradecyl 2,2'-oxydiacetate
7 C36H70O5 dihexadecyl 2,2'-oxydiacetate
8 CO2 carbon dioxide
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
  • 8
  • 1
  • Mole fraction - 1 ; Gas
  • Temperature, K; Gas
  • Pressure, kPa; Gas
  • Gas
  • Liquid
  • static analytical
  • 15
  • POMD
  • 8
  • 2
  • Mole fraction - 2 ; Gas
  • Temperature, K; Gas
  • Pressure, kPa; Gas
  • Gas
  • Liquid
  • static analytical
  • 15
  • POMD
  • 8
  • 3
  • Mole fraction - 3 ; Gas
  • Temperature, K; Gas
  • Pressure, kPa; Gas
  • Gas
  • Liquid
  • static analytical
  • 15
  • POMD
  • 4
  • 8
  • Mole fraction - 4 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 4
  • static analytical
  • 15
  • POMD
  • 8
  • 5
  • Mole fraction - 5 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 5
  • static analytical
  • 15
  • POMD
  • 8
  • 6
  • Mole fraction - 6 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 6
  • static analytical
  • 15
  • POMD
  • 8
  • 7
  • Mole fraction - 7 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 7
  • static analytical
  • 15