Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Phase equilibria of phenol + toluene + quaternary ammonium salts for the separation of phenols from oil with forming deep eutectic solvents

Lin, Z.[Zengqi], Hou, Y.[Yucui], Ren, S.[Shuhang], Ji, Y.[Youan], Yao, C.[Congfei], Niu, M.[Muge], Wu, W.[Weize]
Fluid Phase Equilib. 2016, 429, 67-75
ABSTRACT
Phenolic compounds (such as phenol, cresol and xylenol), which are basic materials for the organic chemical industry, are mainly produced from coal liquefaction oil, coal tar, petroleum, and biomass pyrolysis oil. It has been reported that the separation of phenols from oil with forming deep eutectic solvents based on quaternary ammonium salt is an efficient and environmentally friendly method. However, the phase equilibrium of quaternary ammonium salt + phenol + oil mixtures has not been reported in the literature. In this work, the phase equilibrium for separating phenol from model oil with choline chloride (ChCl), tetraethylammonium chloride (TEAC), and tetramethylammonium chloride (TMAC) was studied. Phase equilibria of three ternary systems of toluene + phenol + quaternary ammonium salt were measured at 25, 40 and 65 deg. C, and phase behaviors of the ternary systems were studied. Effects of temperature, type and dosage of quaternary ammonium salt on the equilibrium were investigated. The results show that low temperatures are beneficial to extraction of phenol and the phenol removal efficiency decreases with increasing temperature. For the quaternary ammonium salts, TEAC has the strongest ability to separate phenol, but the concentration of toluene entrained in the DES phase is the largest. Only TMAC is dissolved in the oil phase to a small extant, which can cause the loss of extractant. ChCl not only has high phenol removal efficiency, but also causes a small concentration of toluene entrained in the DES phase, which shows that ChCl is an efficient and environmentally friendly extractant.
Compounds
# Formula Name
1 C5H14ClNO choline chloride
2 C8H20ClN tetraethylammonium chloride
3 C4H12ClN tetramethylammonium chloride
4 C6H6O phenol
5 C7H8 toluene
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
  • 5
  • 4
  • Mass fraction - 4 ; Liquid mixture 1
  • Mass fraction - 4 ; Liquid mixture 2
  • Mass fraction - 5 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Mass fraction - 5; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 15
  • POMD
  • 2
  • 5
  • 4
  • Mass fraction - 4 ; Liquid mixture 2
  • Mass fraction - 4 ; Liquid mixture 1
  • Mass fraction - 5 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Mass fraction - 5; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 18
  • POMD
  • 3
  • 5
  • 4
  • Mass fraction - 4 ; Liquid mixture 1
  • Mass fraction - 4 ; Liquid mixture 2
  • Mass fraction - 5 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Mass fraction - 5; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 9