Designer solvent ability of alcohols in aqueous biphasic systems composed of deep eutectic solvents and potassium phosphate

Abstract Deep eutectic solvents (DES) have been proposed as phase forming components of aqueous biphasic systems (ABS). However, the DES hydrogen bonding complexes are not stable in the high concentrations of water present in this type of systems. Therefore, as previously shown, DES-based ABS should be treated as quaternary systems. This confers DES-based ABS with an extra degree of freedom for the design of separation processes since while one of the DES components acts as a phase forming component, the other could induce the modification of the ABS phase properties and, consequently, the control of the partition of various biomolecules. In this context, the designer solvent effect of the hydrogen bond donor (HBD), using four different alcohols – ethanol, n-propanol 1,2-propanediol and ethylene glycol – mixed at three different molar fractions (2:1; 1:1 and 1:2) with cholinium chloride (the hydrogen bond acceptor, HBA) in quaternary systems composed of K2HPO4 and water, was evaluated in this work. The results show that the presence of the HBD has an impact upon the liquid–liquid equilibrium, and these changes are dependent on the alcohol nature. The NRTL model was correlated to the tie-line experimental data with a low mean deviation. Moreover, several biomolecules (phenolic compounds, alkaloids, and amino acids) were use as molecular probes to evaluate the ability of alcohols to tune the partition in the studied systems. The alcohol presence changes the properties of the ABS’s phases and it is here shown that the HBD of the DES can indeed be used to modulate the partition behavior of target molecules.

[1]  Juan A Asenjo,et al.  Aqueous two-phase systems for protein separation: a perspective. , 2011, Journal of chromatography. A.

[2]  J. Coutinho,et al.  Ionic liquids as adjuvants for the tailored extraction of biomolecules in aqueous biphasic systems , 2010 .

[3]  Geert-Jan Witkamp,et al.  Natural deep eutectic solvents as new potential media for green technology. , 2013, Analytica chimica acta.

[4]  Thomas de Quincey [C] , 2000, The Works of Thomas De Quincey, Vol. 1: Writings, 1799–1820.

[5]  S. Moore,et al.  A modified ninhydrin reagent for the photometric determination of amino acids and related compounds. , 1954, The Journal of biological chemistry.

[6]  Shu’ni Li,et al.  Liquid–liquid equilibria for water + 1-propanol/2-propanol + potassium chloride + cesium chloride quaternary systems at 298.1 ± 0.1 K , 2008 .

[7]  Kaijia Xu,et al.  Ternary and binary deep eutectic solvents as a novel extraction medium for protein partitioning , 2016 .

[8]  F. O. Farias,et al.  Is It Possible To Create Ternary-like Aqueous Biphasic Systems with Deep Eutectic Solvents? , 2017 .

[9]  D. Prazeres,et al.  Purification of plasmid DNA with aqueous two phase systems of PEG 600 and sodium citrate/ammonium sulfate , 2009 .

[10]  João A. P. Coutinho,et al.  Are Aqueous Biphasic Systems Composed of Deep Eutectic Solvents Ternary or Quaternary Systems , 2016 .

[11]  이화영 X , 1960, Chinese Plants Names Index 2000-2009.

[12]  Marco Rito-Palomares,et al.  Aqueous Two-Phase Systems , 2011 .

[13]  Thermodynamic modelling of phase equilibrium for water + poly(Ethylene glycol) + salt aqueous two-phase systems , 2002 .

[14]  Emma L. Smith,et al.  Deep eutectic solvents (DESs) and their applications. , 2014, Chemical reviews.

[15]  Kaijia Xu,et al.  A green deep eutectic solvent-based aqueous two-phase system for protein extracting. , 2015, Analytica chimica acta.

[16]  Yonghua Wang,et al.  Aqueous two-phase system based on natural quaternary ammonium compounds for the extraction of proteins. , 2016, Journal of separation science.

[17]  F. O. Farias,et al.  Is It Possible To Create Ternary-like Aqueous Biphasic Systems with Deep Eutectic Solvents ? , 2017 .

[18]  J. Coutinho,et al.  Switchable (pH-Driven) Aqueous Biphasic Systems formed by Ionic Liquids as Integrated Production-Separation Platforms. , 2017, Green chemistry : an international journal and green chemistry resource : GC.

[19]  Siyu Yang,et al.  Phase equilibria and salt effect on the aqueous two-phase system of ethanol + 2-propanol + salt [(NH4)2SO4/Na2SO4] + water , 2017, Journal of Thermal Analysis and Calorimetry.

[20]  J. Chen,et al.  Deep eutectic solvents as novel extraction media for protein partitioning. , 2014, The Analyst.

[21]  F. O. Farias,et al.  Study of the pseudo-ternary aqueous two-phase systems of deep eutectic solvent (choline chloride:sugars) + K2HPO4 + water , 2017 .

[22]  J. Coutinho,et al.  Thermoreversible (Ionic-Liquid-Based) Aqueous Biphasic Systems , 2016, Scientific Reports.

[23]  F. Tjerneld,et al.  Partition of proteins in aqueous polymer two-phase systems and the effect of molecular weight of the polymer. , 1987, Biochimica et biophysica acta.

[24]  Yongsheng Yan,et al.  Phase Diagrams of Ammonium Sulfate + Ethanol/1-Propanol/2-Propanol + Water Aqueous Two-Phase Systems at 298.15 K and Correlation , 2010 .

[25]  Lynn F. Gladden,et al.  Glycerol eutectics as sustainable solvent systems , 2010 .

[26]  Kaijia Xu,et al.  Development of green betaine-based deep eutectic solvent aqueous two-phase system for the extraction of protein. , 2016, Talanta.

[27]  John A. Nelder,et al.  A Simplex Method for Function Minimization , 1965, Comput. J..

[28]  João A P Coutinho,et al.  Aqueous biphasic systems: a boost brought about by using ionic liquids. , 2012, Chemical Society reviews.

[29]  David L. Jones,et al.  Simple method to enable the high resolution determination of total free amino acids in soil solutions and soil extracts , 2002 .

[30]  J. Coutinho,et al.  A Triple Salting-Out Effect is Required for the Formation of Ionic-Liquid-Based Aqueous Multiphase Systems. , 2017, Angewandte Chemie.

[31]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[32]  Ana M. Azevedo,et al.  Partitioning of human antibodies in polyethylene glycol–sodium citrate aqueous two-phase systems , 2009 .

[33]  J. Prausnitz,et al.  LOCAL COMPOSITIONS IN THERMODYNAMIC EXCESS FUNCTIONS FOR LIQUID MIXTURES , 1968 .

[34]  J. Coutinho,et al.  Lipase purification using ionic liquids as adjuvants in aqueous two-phase systems , 2015 .

[35]  APPLICATION OF A GENERALIZED MAXIMUM LIKELIHOOD METHOD IN THE REDUCTION OF MULTICOMPONENT LIQUID-LIQUID EQUILIBRIUM DATA , 1997 .