Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Measurements of the solubilities of derivatized amino acids in supercritical carbon dioxide

Freitag, J.[Joerg], Yokoyama, Y.[You], Kuramochi, H.[Hidetoshi], Kawamoto, K.[Katsuya], Nagahama, K.[Kunio], Kato, S.[Satoru]
Fluid Phase Equilib. 2007, 257, 2, 201-206
ABSTRACT
The solubilities of phenylalanine and tyrosine in supercritical carbon dioxide (SCCO2) were measured after derivatization as the N-acetyl amino acid ethyl ester, N-carbobenzoxy amino acid and N-acetyl amino acid. Using an SCCO2 flow system, a measuring method of the saturated solubilities of the derivatized amino acids was established in which the contact height of the extraction cell, i.e. a packed column, is increased till the concentration of a derivatized amino acid at the exit of the cell reaches a plateau. The solubilities of N-acetyl phenylalanine ethyl ester (APEE) exceeded 0.001 mole fraction, which is higher than those of caffeine produced in industrial SCCO2 processes. A possible way of separating the amino acid mixtures using polarity differences in different amino acid side chains was demonstrated using the solubility data of the N-acetyl-amino acid ethyl esters in SCCO2, as the solubilities of APEE are higher than those of N-acetyl tyrosine ethyl ester by two orders of magnitude.
Compounds
# Formula Name
1 C13H17NO3 N-acetyl-L-phenylalanine, ethyl ester
2 C11H13NO3 acetyl-L-phenylalanine
3 C17H17NO4 ((benzyloxy)carbonyl)-L-phenylalanine
4 C13H17NO4 N-acetyl-L-tyrosine, ethyl ester
5 C11H13NO4 acetyl-L-tyrosine
6 C17H17NO5 N-[(phenylmethoxy)carbonyl]-L-tyrosine
7 CO2 carbon dioxide
8 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 Constraint Phase Method #Points
  • POMD
  • 7
  • 1
  • Mole fraction - 1 ; 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 - 1
  • Chromatography
  • 11
  • POMD
  • 7
  • 2
  • Mole fraction - 2 ; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 2
  • Chromatography
  • 5
  • POMD
  • 7
  • 3
  • Mole fraction - 3 ; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 3
  • Chromatography
  • 5
  • POMD
  • 7
  • 4
  • 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
  • Chromatography
  • 11
  • POMD
  • 7
  • 5
  • Mole fraction - 5 ; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 5
  • Chromatography
  • 5
  • POMD
  • 7
  • 6
  • Mole fraction - 6 ; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 6
  • Chromatography
  • 5
  • POMD
  • 1
  • 8
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 4
  • 8
  • Mole fraction - 4 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • Chromatography
  • 3