Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Designing eutectic mixtures for the extraction of 2-phenylethanol (PEA) from aqueous phase

Domanska, U.[Urszula], Wieckowski, M.[Mikolaj], Okuniewska, P.[Patrycja]
Fluid Phase Equilib. 2017, 447, 84-94
ABSTRACT
The field of industrial biotechnology is rapidly growing. This includes the use of biosynthesis of the fragrance-row materials in chemical industry, food industry, cosmetical and pharmaceutical industry. The production of 2-phenylethanol (PEA), which is an important flavor and fragrance compound, with a rose-like odor has been significantly increased last decade. The ionic liquids (ILs) and binary eutectic solvents (BES) are proposed as an entrainers for the extraction of PEA in a biphasic biosynthesis. ILs and BES reveal many unique properties which make them very interesting for applications in modern green technologies. In this work we present new experimental results on (solid, or liquid + liquid) phase equilibrium (SLE/LLE) measurements of twelve binary systems composed of pyrrolidinium-based ILs (namely: 1-butyl-1-methylpyrrolidinium chloride, [BMPYR][Cl] and 1-butyl-1-methylpyrrolidinium bis{(trifluoromethyl)sulfonyl}imide [BMPYR][NTf2] as well as 1-hexyl-1-methylpyrrolidinium chloride, [HMPYR][Cl] and 1-hexyl-1- methylpyrrolidinium bis{(trifluoromethyl)sulfonyl}imide [HMPYR][NTf2] with alcohols (1-decanol, 2-methyl-1-butanol, 2-methyl-2-butanol) and oleic acid. Additionally, three ternary LLE mixtures are presented {IL, or BES + PEA + water} at T = 308.15 K and ambient pressure. The data reveals that [HMPYR][NTf2] ionic liquid is more attractive than [BMPYR][NTf2] and that BESs mixtures ([BMPYR][NTf2] + 2-methyl-2-butanol) and ([BMPYR][NTf2] + 2-methyl-2-butanol) present worst selectivities and solute distribution ratios than those observed for pure ILs. However, they may be assumed as an alternative, less cost, solvents for the separation of PEA from the water phase using liquid-liquid extraction at ambient conditions.
Compounds
# Formula Name
1 C9H20ClN 1-butyl-1-methylpyrrolidinium chloride
2 C11H20F6N2O4S2 1-butyl-1-methylpyrrolidinium bis[(trifluoromethyl)sulfonyl]imide
3 C11H24ClN 1-hexyl-1-methylpyrrolidinium chloride
4 C13H24F6N2O4S2 1-hexyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide
5 C8H10O 2-phenylethanol
6 C10H22O decan-1-ol
7 C5H12O 2-methyl-1-butanol
8 C5H12O 2-methylbutan-2-ol
9 C18H34O2 (Z)-9-octadecenoic acid
10 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
  • 1
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Triple point temperature, K ; Crystal 3
  • Crystal 3
  • Crystal 2
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 3
  • Crystal 3
  • Crystal 2
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 2
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 2
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 3
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 4
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 8
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 9
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 9
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 9
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 9
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 9
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 6
  • 1
  • Eutectic temperature, K ; Crystal - 1
  • Crystal - 1
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • 1
  • Eutectic composition: mole fraction - 1 ; Crystal - 1
  • Crystal - 1
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 6
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 12
  • POMD
  • 6
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • VISOBS
  • 8
  • POMD
  • 7
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 8
  • POMD
  • 8
  • 1
  • Eutectic temperature, K ; Crystal - 1
  • Crystal - 1
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 8
  • 1
  • Eutectic composition: mole fraction - 1 ; Crystal - 1
  • Crystal - 1
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 8
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 14
  • POMD
  • 8
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • VISOBS
  • 6
  • POMD
  • 9
  • 1
  • Eutectic temperature, K ; Crystal - 1
  • Crystal - 1
  • Liquid
  • Crystal - 9
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 9
  • 1
  • Eutectic composition: mole fraction - 1 ; Crystal - 1
  • Crystal - 1
  • Liquid
  • Crystal - 9
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 9
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 8
  • POMD
  • 9
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • VISOBS
  • 7
  • POMD
  • 6
  • 2
  • Eutectic temperature, K ; Crystal - 2
  • Crystal - 2
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • 2
  • Eutectic composition: mole fraction - 2 ; Crystal - 2
  • Crystal - 2
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 6
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 15
  • POMD
  • 6
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 9
  • POMD
  • 6
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • VISOBS
  • 11
  • POMD
  • 7
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 27
  • POMD
  • 7
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • VISOBS
  • 10
  • POMD
  • 8
  • 2
  • Eutectic temperature, K ; Crystal - 2
  • Crystal - 2
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 8
  • 2
  • Eutectic composition: mole fraction - 2 ; Crystal - 2
  • Crystal - 2
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 8
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 25
  • POMD
  • 8
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 13
  • POMD
  • 8
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • VISOBS
  • 7
  • POMD
  • 9
  • 2
  • Eutectic temperature, K ; Crystal - 2
  • Crystal - 2
  • Liquid
  • Crystal - 9
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 9
  • 2
  • Eutectic composition: mole fraction - 2 ; Crystal - 2
  • Crystal - 2
  • Liquid
  • Crystal - 9
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 9
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 8
  • POMD
  • 9
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 3
  • POMD
  • 9
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • VISOBS
  • 9
  • POMD
  • 6
  • 3
  • Eutectic temperature, K ; Crystal - 3
  • Crystal - 3
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • 3
  • Eutectic composition: mole fraction - 3 ; Crystal - 3
  • Crystal - 3
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 6
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 14
  • POMD
  • 6
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • VISOBS
  • 14
  • POMD
  • 7
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 9
  • POMD
  • 8
  • 3
  • Eutectic temperature, K ; Crystal - 3
  • Crystal - 3
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 8
  • 3
  • Eutectic composition: mole fraction - 3 ; Crystal - 3
  • Crystal - 3
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 8
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 18
  • POMD
  • 8
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • VISOBS
  • 7
  • POMD
  • 9
  • 3
  • Eutectic temperature, K ; Crystal - 3
  • Crystal - 3
  • Liquid
  • Crystal - 9
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 9
  • 3
  • Eutectic composition: mole fraction - 3 ; Crystal - 3
  • Crystal - 3
  • Liquid
  • Crystal - 9
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 9
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 10
  • POMD
  • 9
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • VISOBS
  • 11
  • POMD
  • 6
  • 4
  • Eutectic temperature, K ; Crystal - 4
  • Crystal - 4
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • 4
  • Eutectic composition: mole fraction - 4 ; Crystal - 4
  • Crystal - 4
  • Liquid
  • Crystal - 6
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 6
  • 4
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 4; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 19
  • POMD
  • 6
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 2
  • POMD
  • 6
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • VISOBS
  • 7
  • POMD
  • 7
  • 4
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 4; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 20
  • POMD
  • 7
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 5
  • POMD
  • 7
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • VISOBS
  • 5
  • POMD
  • 8
  • 4
  • Eutectic temperature, K ; Crystal - 4
  • Crystal - 4
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 8
  • 4
  • Eutectic composition: mole fraction - 4 ; Crystal - 4
  • Crystal - 4
  • Liquid
  • Crystal - 8
  • Air at 1 atmosphere
  • Derived from phase diagram analysis
  • 1
  • POMD
  • 8
  • 4
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 4; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 15
  • POMD
  • 8
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 7
  • POMD
  • 8
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • VISOBS
  • 8
  • POMD
  • 9
  • 4
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 4; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 5
  • POMD
  • 9
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 2
  • POMD
  • 5
  • 10
  • 2
  • Mole fraction - 5 ; Liquid mixture 2
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 2 ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 13
  • POMD
  • 10
  • 2
  • Mole fraction - 2 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 10
  • 2
  • Mole fraction - 2 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • 1
  • POMD
  • 5
  • 10
  • Mole fraction - 5 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 5
  • 10
  • Mole fraction - 5 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • 1