Extraction of 2-Phenylethanol (PEA) from Aqueous Solution Using Ionic Liquids: Synthesis, Phase Equilibrium Investigation, Selectivity in Separation, and Thermodynamic Models (original) (raw)
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The Journal of Chemical Thermodynamics, 2016
This work presents some important issues and topics related to possible extraction of 2-phenylethanol (PEA) from aqueous phase ''in situ" during the biosynthesis with ionic liquids (ILs). It consists of a series of experimental phase equilibrium measurements in binary and ternary systems. Three ILs as extraction media are proposed for the extraction process based on phase equilibria in ternary systems {IL (1) + PEA (2) + water (3)} at temperature T = 308.15 K and ambient pressure. The systems are composed of the following ILs: 1-hexyl-1-methylmorpholinium bis{(trifluoromethyl)sulfonyl}imide, [HMMOR][NTf 2 ], 1-allyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}imide, [AMIM][NTf 2 ], and diethylmethylsulfonium bis{(trifluoromethyl)sulfonyl}imide, [S 221 ][NTf 2 ]. A differential scanning calorimetry (DSC) was used to determine the thermal properties of the ILs. The synthesis of new [HMMOR][NTf 2 ] IL and its thermal and physicochemical properties as density, viscosity, surface tension were presented. The volume expansivity, as well as the surface thermodynamic functions, such as surface entropy and enthalpy have been derived from the temperature dependence of the surface tension values, as well as the critical temperature, parachor and speed of sound for all ILs were presented. The correlation of the liquidus curves in binary systems and tie-lines in ternary systems was undertaken with the NRTL equation. These results of solubility can be used to design future alternative technological processes of the extraction of PEA from fermentation broth.
The Journal of Physical Chemistry B, 2009
Extractive fermentation using aqueous biphasic systems (ABS) is a promising separation process since it provides a nondenaturing environment for biomolecules and improves the stability of cells. Due to environmental concerns and toxicity issues related with common volatile organic solvents, ionic liquids (ILs), a new class of nonvolatile alternative solvents, are being currently investigated for extraction purposes. In this work, a wide range of imidazolium-based ILs was studied aiming at obtaining new insights regarding their ability toward the formation of ABS and their capacity to the extraction of biomolecules. On the basis of the IL cations 1-ethyl-3-methylimidazolium and 1-butyl-3-methylimidazolium, the IL anion influence on ABS formation was assessed through their combination with chloride, bromide, acetate, hydrogensulfate, methanesulfonate, methylsulfate, ethylsulfate, trifluomethanesulfonate, trifluoroacetate, and dicyanamide. Ternary phase diagrams (and respective tie-lines) formed by these hydrophilic ILs, water, and the inorganic salt K 3 PO 4 , were measured and are reported. The results indicate that the ability of an IL to induce ABS closely follows the decrease in the hydrogen bond accepting strength or the increase in the hydrogen bond acidity of the IL anion. In addition, the extraction capacity of the studied ABS was evaluated through their application to the extraction of an essential amino acid, L-tryptophan. It is shown that the partition coefficients obtained between the IL and the K 3 PO 4 -aqueous rich phases were substantially larger than those typically obtained with polymers-inorganic salts or polymers-polysaccharides aqueous systems.
Journal of Physical Chemistry B, 2009
Extractive fermentation using aqueous biphasic systems (ABS) is a promising separation process since it provides a nondenaturing environment for biomolecules and improves the stability of cells. Due to environmental concerns and toxicity issues related with common volatile organic solvents, ionic liquids (ILs), a new class of nonvolatile alternative solvents, are being currently investigated for extraction purposes. In this work, a wide range of imidazolium-based ILs was studied aiming at obtaining new insights regarding their ability toward the formation of ABS and their capacity to the extraction of biomolecules. On the basis of the IL cations 1-ethyl-3-methylimidazolium and 1-butyl-3-methylimidazolium, the IL anion influence on ABS formation was assessed through their combination with chloride, bromide, acetate, hydrogensulfate, methanesulfonate, methylsulfate, ethylsulfate, trifluomethanesulfonate, trifluoroacetate, and dicyanamide. Ternary phase diagrams (and respective tie-lines) formed by these hydrophilic ILs, water, and the inorganic salt K 3 PO 4 , were measured and are reported. The results indicate that the ability of an IL to induce ABS closely follows the decrease in the hydrogen bond accepting strength or the increase in the hydrogen bond acidity of the IL anion. In addition, the extraction capacity of the studied ABS was evaluated through their application to the extraction of an essential amino acid, L-tryptophan. It is shown that the partition coefficients obtained between the IL and the K 3 PO 4 -aqueous rich phases were substantially larger than those typically obtained with polymers-inorganic salts or polymers-polysaccharides aqueous systems.
This work focusses on the application and pre-screening of selected ILs for different industrial separation problems based on limiting activity coefficients at infinite dilution, and liquid-liquid equilibrium data at different temperatures. The selected ionic liquids for pre-screening based on activity coefficients at infinite dilution data include (1,3- dimethyimidazolium dimethylphosphate, trioctylmethylammonium chloride, trihexyltetradecylphosphonium dicyanamide, 2,3-dihydroxypropyl-N-methyl-2- oxopyrrolidinium chloride, 2,3-epoxypropyl methyl-2-oxopyrrolidinium chloride) and deep eutectic solvent (1-butyl-3-methylimidazolium chloride + glycerol) at 1:2 molar ratio. These ionic liquids were tested in 33 solutes (alkanes, alkenes, alkynes, alcohols, tetrahydrofuran, ketones, aromatic hydrocarbons, thiophene, acetonitrile) and water at T = (313 – 343) K and at p = 101 kPa. The use of ionic liquid as a stationary phase on the column loading ranged between (30 – 36) % by mass. Thermo...
The Journal of Chemical Thermodynamics, 2018
The present work was focused on the study of two imidazolium-based ionic liquids (ILs) as solvents in liquid-liquid extraction of ethanol from aqueous mixtures. With this aim, the experimental liquid-liquid equilibria (LLE) data of water (1) + ethanol (2) + 1ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([emim][Tf 2 N]) (3) and water (1) + ethanol (2) + 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([hmim][Tf N]) (4) systems were obtained at different temperatures: 283.2, 303.2, and 323.2 K, in order to check the influence of temperature. The results were correlated by non-random two-liquid (NRTL) and universal quasichemical (UNIQUAC) models with good concordance in both cases. Finally, the ability of the two ILs to act as solvents was studied by evaluating the coefficient distribution and the selectivity of ternary systems and compared with another IL from the literature.
The Journal of Chemical Thermodynamics, 2018
The separation of olefins/paraffins is a challenge for the petrochemical industry due to the close boiling points of these hydrocarbons. In this work we have studied the feasibility of different imidazolium and pyridinium-based ionic liquids (ILs) as alternative solvents in the cyclohexane/cyclohexene separation. Five ILs have been studied, namely 1-butyl-4methylpyridinium tricyanomethanide ([4bmpy][TCM]), bis(1-ethyl-3-methylimidazolium) tetrathiocyanatocobaltate ([emim] 2 [Co(SCN) 4 ]), bis(1-butyl-3-methylimidazolium) tetrathiocyanatocobaltate ([bmim] 2 [Co(SCN) 4 ]), 1-ethyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide ([4empy][Tf 2 N]), and 1-butyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide ([4bmpy][Tf 2 N]). Experimental liquid-liquid equilibrium (LLE) data were obtained for the equimolar ternary mixtures {cyclohexane (1) + cyclohexene (2) + IL (3)} at T = (298.2, 313.2 and 328.2) K and atmospheric pressure in order to study the effect of the temperature on the extractive properties. Afterwards, LLE data for every ternary system was determined at the best temperature and for the whole cyclohexane/cyclohexene composition range. These ILs have shown promising results in terms of distribution ratio and selectivity, showing the [4bmpy][TCM] IL the best extractive properties at 298.2 K and atmospheric pressure. The Non-Random Two Liquids (NRTL) model was used to successfully correlate the experimental LLE data.
Liquid-Liquid Extraction in Systems Containing Butanol and Ionic Liquids – A Review
Chemical and Process Engineering, 2017
Room-temperature ionic liquids (RTILs) are a moderately new class of liquid substances that are characterized by a great variety of possible anion-cation combinations giving each of them different properties. For this reason, they have been termed as designer solvents and, as such, they are particularly promising for liquid-liquid extraction, which has been quite intensely studied over the last decade. This paper concentrates on the recent liquid-liquid extraction studies involving ionic liquids, yet focusing strictly on the separation of n-butanol from model aqueous solutions. Such research is undertaken mainly with the intention of facilitating biological butanol production, which is usually carried out through the ABE fermentation process. So far, various sorts of RTILs have been tested for this purpose while mostly ternary liquid-liquid systems have been investigated. The industrial design of liquid-liquid extraction requires prior knowledge of the state of thermodynamic equilib...
The Journal of Chemical Thermodynamics, 2012
In this work, the ionic liquids 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [EMim] [NTf 2 ], 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [BMim][NTf 2 ], 1-butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide, [BMpy][NTf 2 ], 1-butyl-3-methylpyridinium trifluoromethanesulfonate, [BMpy][TfO], have been investigated for their use as solvents in extraction processes for the ethanol removal from its azeotropic mixture with hexane. Therefore, the experimental determination of the liquid + liquid equilibrium for the ternary systems {hexane (1) + ethanol (2) + [EMim][NTf 2 ] (3)}, {hexane (1) + ethanol (2) + [BMim][NTf 2 ] (3)}, {hexane (1) + ethanol (2) + [BMpy][NTf 2 ] (3)} and {hexane (1) + ethanol (2) + [BMpy][TfO] (3)} was carried out at T = 298.15 K and atmospheric pressure. Classical parameters such as selectivity and solute distribution ratio, derived from the tie-line data, were calculated and afterwards, the structural influence of the ionic liquids on the extraction process was analyzed. Finally, the experimental LLE data were correlated by means of the NRTL and UNIQUAC models.
Application of Ionic Liquids in Separation and Fractionation Processes
2018
Aqueous biphasic systems Liquid-liquid systems formed by two water-soluble components dissolved in water, which above given concentrations form two phases. Biorefinery Facility with integrated processes to convert biomass into energy, fuels, materials, and commodity and value-added chemicals. Green chemistry Concept addressing the design of chemical products and processes aiming at reduce or eliminate the use and generation of hazardous substances. Ionic liquids Low melting temperature salts, composed of organic cations and organic/inorganic anions. Natural products Compounds that can be obtained from biomass. Solid-liquid extraction Process in which a solvent is added to solid biomass samples in order to extract target compounds. Definition of the Subject