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

Farias, Fabiane Oliveira; Passos, Helena; Sanglard, Matheus Gomes; Igarashi‐Mafra, Luciana; Coutinho, João A. P.; Mafra, Marcos R.

doi:10.1016/j.seppur.2018.02.029

Cited by 51 publications

(56 citation statements)

References 33 publications

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“…They found that at the same solvent composition, the affinity of amino acids to concentrate in the water-rich phase follows the trend serine > glycine > alanine, which is in close agreement with the trend obtained here for the ability of the amino acids to solute out 1-butanol from aqueous media. Previously, Mafra and co-workers studied the partition behavior of several amino acids (glycine, tyrosine, phenylalanine, and tryptophan) in the deep eutectic solvent (DES)-based aqueous triphasic systems composed of choline chloride ([Ch]Cl, the hydrogen bond acceptor)-propanol (the hydrogen bond donor) + K 2 HPO 4 aqueous solutions . They found that the amino acids, tyrosine, phenylalanine, and tryptophan, are mainly partitioned to the [Ch]Cl-rich phase (middle phase), the amino acid glycine is preferentially partitioned to the K 2 HPO 4 -rich phase (bottom phase), and none of the amino acids tend to concentrate in the hydrophobic propanol-rich phase (top phase) .…”

Section: Resultsmentioning

confidence: 99%

Soluting-In, Soluting-Out, and Washing-Out Effects of Various Additives on Aqueous 1-Butanol Solutions

2021

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This work addresses the liquid−liquid demixing (clouding) behavior of 1-butanol aqueous solutions in the presence of various additives, including amino acids, imidazolium-based ionic liquids (ILs), polymers, and 1-/2-propanol, in a wide temperature range (283.1−353.1 K) and at atmospheric pressure (845 hPa). The visual cloud point data revealed that the studied amino acids reduce the water solubility of 1-butanol and expand the immiscibility region (soluting-out effect). At the same amino acid's molality, the soluting-out aptitude follows the trend serine > glycine > alanine > proline > glutamine. However, the ILs and polymers [poly(ethylene glycol) (PEG)] act as cosolvents for 1butanol in aqueous media and broaden the miscibility region (soluting-in effect). An increase in the cation alkyl chain length of ILs and a decrease in PEG molar mass strengthen the soluting-in effect. The clouding phase behavior of aqueous 1-butanol + 1-/2propanol ternary systems at lower temperatures reveals the expansion of the immiscibility region due to the washing-out effect but at higher temperatures exhibits the soluting-in effect. An increase in the concentration of 1-/2-propanol decreases the extent of the washing-out effect. In all cases, the soluting-in/out effects increase with the increase in the concentration of additives. Soluting effects occurring in the studied systems have been quantified by correlating the experimental cloud point data with Setschenow's equation, and the clouding process in the systems studied has been carefully discussed from the thermodynamic point of view. From the gathered results, at higher temperatures, the relative contribution of enthalpy to clouding Gibbs free energy in the presence of soluting-in agent additives is mostly higher than that in the presence of soluting-out agents. However, at lower temperatures, the entropy increase is the driving force of clouding in most of the investigated systems.

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Section: Resultsmentioning

confidence: 99%

Soluting-In, Soluting-Out, and Washing-Out Effects of Various Additives on Aqueous 1-Butanol Solutions

2021

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“…The properties of the liquids (such as viscosity, conductivity, density and so on) can be also tailored by specific amounts of added water in DESs mixtures; i.e., their viscosity can drastically decrease even with small amounts of added water. Other relevant DESs in this topic are the hydrophobic ones: mixtures that are formed by H-bonds but that can be separated from water only by the use of hydrophobic HBD components [33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Probing the structural features and the micro-heterogeneity of various deep eutectic solvents and their water dilutions by the photophysical behaviour of two fluorophores

Tiecco

Guida

Gentili

et al. 2021

Journal of Molecular Liquids

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“…Over the last years, DESs composed of different HBAs (e.g., betaine, choline chloride, and quaternary ammonium salts) and HBDs (e.g., alcohols, carbohydrates, and organic acids) have been tested in ABS formation and the main focus was put on their applicability in the partition of various molecules, including biomolecules. Although, in the first reports, ABSs formed with DESs were described as ternary systems and a DES-rich and a salt-rich phase were considered to coexist, ,− later it was proven that such ABSs are in fact quaternary systems. − The reason for this fact is that DES components are solvated by water leading to the breakage of the hydrogen bond between the HBA and HBD. , As a result, DES components partition independently to both phases, where one of them acts as an additive, enabling the manipulation of the equilibrium and the phase polarities. , Consequently, similarly to IL-based ABSs, these ABSs allowed us to overcome the problems encountered while using polymer-based ABSs, where the restricted polarity and low selectivity were usually observed.…”

Section: Introductionmentioning

confidence: 99%

“…18,22 As a result, DES components partition independently to both phases, where one of them acts as an additive, enabling the manipulation of the equilibrium and the phase polarities. 19,21 Consequently, similarly to IL-based ABSs, these ABSs allowed us to overcome the problems encountered while using polymer-based ABSs, where the restricted polarity and low selectivity were usually observed.…”

Section: ■ Introductionmentioning

confidence: 99%

Novel Acidic Deep Eutectic Solvent-Based Aqueous Biphasic Systems for Efficient Extraction of Pepsin

Marchel

Coroadinha

Marrucho

2020

ACS Sustainable Chem. Eng.

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Owning to its unique properties of breaking down proteins into soluble small peptides, pepsin has been advantageously applied in many different industries, such as food, feed, or pharmaceuticals. However, industrial production of enzymes is still considered a major bottleneck because of the lack of robust, cost-effective, and sustainable purification methods, which can account for up to 65% of the total manufacturing cost. In this work, the potential of betaine hydrochloride (BeHCl)- and BeHCl-based deep eutectic solvents (DESs) as a phase-forming compound of aqueous biphasic systems (ABSs) for the simultaneous extraction and recovery of pepsin is investigated as a sustainable integrated ABS platform for enzyme production. Liquid–liquid equilibrium (LLE) of ABSs composed of polypropylene glycol and DES composed of BeHCl, as a hydrogen-bond acceptor (HBA), and fructose, glucose, sucrose, and urea, as hydrogen-bond donors (HBDs), was measured at a temperature of 25 °C and atmospheric pressure and is presented here. It is shown that the salting-out ability of the HBA is a driving force for ABS formation, and the HBDs act as additives, leading to either increase or decrease in the biphasic region, depending on their chemical structure. The biocompatibility of the prepared DESs and their components was studied using two different human cell lines, HEK 293 and Huh-7. It is shown that these DESs are less toxic at higher concentrations than their separate components. The partitioning studies revealed high affinity of pepsin to the BeHCl-enriched phase in all the studied systems. Very high extraction efficiencies and pepsin recovery yield, above 96 and 141.9%, respectively, were obtained and it was possible to significantly increase the pepsin activity recovery yield up to 141.9% in the BeHCl:glucose-based ABSs. In conclusion, the ABSs formed with DESs allow the development of a promising platform to simultaneously extract, recover, and formulate the BeHCl-pepsin drug, without the need to remove the phase-forming compounds or recover the enzyme from the BeHCl-enriched phase, thus improving sustainability in pharmaceutical manufacturing.

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

Cited by 51 publications

References 33 publications

Soluting-In, Soluting-Out, and Washing-Out Effects of Various Additives on Aqueous 1-Butanol Solutions

Soluting-In, Soluting-Out, and Washing-Out Effects of Various Additives on Aqueous 1-Butanol Solutions

Probing the structural features and the micro-heterogeneity of various deep eutectic solvents and their water dilutions by the photophysical behaviour of two fluorophores

Novel Acidic Deep Eutectic Solvent-Based Aqueous Biphasic Systems for Efficient Extraction of Pepsin

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