Extraction of 2-phenylethanol (PEA) from aqueous phases using tetracyanoborate-based ionic liquids

Królikowski, Marek; Pachla, Julita; Ramjugernath, Deresh; Naidoo, Paramespri; Domańska, Urszula

doi:10.1016/j.molliq.2016.10.041

Cited by 12 publications

(18 citation statements)

References 35 publications

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“…As usual, the complete miscibility in the liquid phase is observed for both ILs in the binary {IL (1) + PEA (2)} system. The solubility of PEA in water is x 2 = 0.582 at T = 308.15 K as it was observed in all our investigations. − …”

Section: Results and Discussionsupporting

confidence: 79%

“…The well-known synthetic method was used for the measurements of solubility of [DoMIM][NTf 2 ] in the saturated solution. , The sample of (IL + PEA) was prepared by weighing. The solution was heated very slowly (<2 K·h –1 ) with continuous stirring inside a Pyrex glass cell placed in a thermostat.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…Many solvents were already described in the literature, such as oleic acid, alcohols, esters, polypropylene glycol 1200, and ionic liquids (ILs) . Recently, intensive investigations were reported using ILs as extractive solvents. − However, ILs are expensive solvents and in many cases are not attractive for the biotransformation, and the enhancement of PEA production in a biphasic system in comparison with traditional organic solvents was observed. ,, …”

Section: Introductionmentioning

confidence: 99%

“…Different ILs were investigated in the ternary liquid–liquid phase equilibrium (LLE) {IL + PEA + water} systems. The imidazolium-, isoquinolinium-, pyrrolidinium-, piperidinium-, ammonium-, morpholinium-, and sulfonium-based ILs with different anions such as bis{(trifluomethyl)sulfonyl}imide [NTf 2 ] − , tetracyanoborate [TCB] − , and bis(fluorosulfonyl)imide (FSI – ). − The best selectivities of PEA extraction ( S 23 ) and solute distribution ratios (β 2 ) were observed in these ternary systems for N -octylisoquinolinium bis{(trifluoromethyl)sulfonyl}imide, [C 8 iQuin][NTf 2 ], for N -methyl- N -trioctylammonium bis{(trifluoromethyl)sulfonyl}imide, [N 1888 ][NTf 2 ], and for N -triethyl- N -octylammonium bis{(trifluoromethyl)sulfonyl}imide, [N 2228 ][NTf 2 ] . In general, the tetracyanoborate-based ILs and bis(fluorosulfonyl)imide-based ILs were less effective in the extraction processes.…”

Section: Introductionmentioning

confidence: 99%

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Phase Equilibrium Investigation on 2-Phenylethanol in Binary and Ternary Systems: Influence of High Pressure on Density and Solid–Liquid Phase Equilibrium

et al. 2018

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Ionic liquids (ILs) are important new solvents proposed for applications in different separation processes. Herein, an idea of possible use of high pressure in a general strategy of production of 2-phenylethanol (PEA) is discussed. In this work, we present the influence of pressure on the density in binary systems of {1-hexyl-1-methylpyrrolidynium bis{(trifluoromethyl)sulfonyl}imide, [HMPYR][NTf], or 1-dodecyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}imide, [DoMIM][NTf] + PEA} in a wide range of temperatures (298.15-348.15 K) and pressures (0.1-40 MPa). The densities at ambient and high pressures are measured to present the physicochemical properties of the ILs used in the process of separation of PEA from aqueous phase. The Tait equation was used for the correlation of density of one-component and two-component systems as a function of mole fraction, temperature, and pressure. The influence of pressure is not significant. These systems exhibit mainly negative molar excess volumes, V. The solid-liquid phase equilibrium (SLE) of [DoMIM][NTf] in PEA at atmospheric pressure was measured and compared to the SLE high-pressure results. Additionally, the ternary liquid-liquid phase equilibrium (LLE) at ambient pressure in the {[DoMIM][NTf] (1) + PEA (2) + water (3)} at temperature T = 308.15 K was investigated. The solubility of water in the [DoMIM][NTf] is quite high in comparison with that measured by us earlier for ILs ( x = 0.403) at T = 308.15 K, which results in not very successful average selectivity of extraction of PEA from the aqueous phase. The [DoMIM][NTf] has shown strong interaction with PEA without the immiscibility region. The ternary system revealed Treybal's type phase equilibrium in which two partially miscible binaries ([DoMIM][NTf] + water) and (PEA + water) exist. From the results of LLE in the ternary system, the selectivity and the solute distribution ratio of separation of water/PEA were calculated and compared to the results obtained for the ILs measured earlier by us. The popular NRTL model was used to correlate the experimental tie-lines in ternary LLE. These results may help in a new technological project of "in situ" extraction of PEA from aqueous phase during the biosynthesis.

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Section: Results and Discussionsupporting

confidence: 79%

Section: Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phase Equilibrium Investigation on 2-Phenylethanol in Binary and Ternary Systems: Influence of High Pressure on Density and Solid–Liquid Phase Equilibrium

et al. 2018

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“…In the food industry, 2-PE improves the aromatic profile of several fermented beverages, and is used as an additive in candies and non-alcoholic beverages (Domańska et al, 2017;Etschmann et al, 2002;Królikowski et al, 2016). However, while products labeled as "natural" are favored by the consumers, 2-PE has been largely produced by chemical synthesis (Lu et al, 2016).…”

mentioning

confidence: 99%

Intensification of 2-phenylethanol production using an aerated system assisted by a membrane-based solvent extraction technique

Cordero-Soto¹,

Castillo‐Araiza²,

Rutiaga-Quiñones³

et al. 2021

RMIQ

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Cyanoborates

Ignat’ev

Finze

2019

Eur J Inorg Chem

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Cyanoborate chemistry has emerged to an important topic during the last two decades, beginning with two independent reports on the successful synthesis of the tetracyanoborate anion [B(CN) 4 ]in 2000. A wealth of cyanoborate anions with different substituents in addition to CN group(s) bonded to boron, i.e. hydrogen, halogen, aryl, alkenyl, alkyl, perfluoroalkyl, and alkoxy, have been developed, which enable the tuning of properties of compounds and materials based on them. The readily accessible alkali metal cyanoborates are convenient starting materials for the preparation of cyanoborates with various organic, inorganic, and metal cations as well as cyanoborate coordination compounds. A focus has been on low-[a] Julius-Maximilians-Universität Würzburg,

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Extraction of 2-phenylethanol (PEA) from aqueous phases using tetracyanoborate-based ionic liquids

Cited by 12 publications

References 35 publications

Phase Equilibrium Investigation on 2-Phenylethanol in Binary and Ternary Systems: Influence of High Pressure on Density and Solid–Liquid Phase Equilibrium

Phase Equilibrium Investigation on 2-Phenylethanol in Binary and Ternary Systems: Influence of High Pressure on Density and Solid–Liquid Phase Equilibrium

Intensification of 2-phenylethanol production using an aerated system assisted by a membrane-based solvent extraction technique

Cyanoborates

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