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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Green Chemistry".

Deadline for manuscript submissions: 30 November 2024 | Viewed by 16072

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Special Issue Editors

Dr. Iuliia V. Voroshylova

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REQUIMTE/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
Interests: molecular dynamics simulations; density functional theory; ionic liquids; deep eutectic solvents; electric double layer; interface; electrolyte; energy storage

Dr. Elisabete Ferreira

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Guest Editor Assistant

REQUIMTE/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
Interests: deep eutectic solvents; molecular dynamics; force field; electrodeposition; surface; electrode; solvent

Special Issue Information

Dear Colleagues,

In recent years, deep eutectic solvents (DESs) have gained significant attention from both academic and industrial communities. This is of no surprise, as DESs are a promising class of solvents with unique properties and potential applications in various fields. DESs are formed by combining two or more components in a specific ratio to create a eutectic mixture that remains liquid at or near room temperature, which makes them suitable for use as solvents for chemical reactions, separations, extractions, biotechnology, and the synthesis of nanoparticles, biomaterials, and pharmaceuticals.

Attractive properties of DESs, such as low volatility, high thermal stability, and high conductivity, means they can be used as potential electrolytes in energy storage devices, such as batteries and supercapacitors. Recent research has focused on optimizing the properties of DES-based electrolytes to improve the performance and stability of these devices.

Besides that, DESs can be considered “green” substances, as long as they are derived from natural compounds such as sugars, amino acids, and choline chloride. There are reports of DESs showing promise as sustainable alternatives to traditional solvents, as they are biodegradable, non-toxic, and renewable. Thus, they can be used in the extraction and purification of bioactive compounds from natural sources, such as plants and fungi. DESs have been found to effectively extract a wide range of compounds, including flavonoids, alkaloids, and terpenoids. DES-based drug delivery systems also seem to be promising.

Overall, the use of DESs in various fields is an active area of research, and new advances are being made all the time. The unique properties of DESs make them promising candidates for a wide range of applications, and their potential as sustainable and green solvents is particularly exciting.

The topics covered in this Special Issue represent recent findings in the synthesis of new DESs, theirs properties, and application in different fields. Both review and original research articles are welcomed, highlighting the latest developments and future challenges in this rapidly growing field.

Dr. Iuliia V. Voroshylova
Guest Editor

Dr. Elisabete Ferreira
Guest Editor Assistant

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Keywords

green chemistry
natural compounds
sustainable processes
solvents
electrolytes
extraction

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Published Papers (12 papers)

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Research

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17 pages, 10109 KiB

Open AccessArticle

Development of Thin Film Microextraction with Natural Deep Eutectic Solvents as ‘Eutectosorbents’ for Preconcentration of Popular Sweeteners and Preservatives from Functional Beverages and Flavoured Waters

by Justyna Werner and Daria Mysiak

Molecules 2024, 29(19), 4573; https://doi.org/10.3390/molecules29194573 - 26 Sep 2024

Viewed by 812

Abstract

An eco-friendly method for the determination of sweeteners (aspartame, acesulfame-K) and preservatives (benzoic acid, sorbic acid, methylparaben, ethylparaben) in functional beverages and flavoured waters using thin film microextraction (TFME) and high-performance liquid chromatography with UV detection (HPLC-UV) was proposed. A series of fourteen green and renewable solidified natural deep eutectic solvents (NADESs) were prepared and tested as ‘eutectosorbents’ in TFME for the first time. In the proposed method, the NADES containing acetylcholine chloride and 1-docosanol at a 1:3 molar ratio was finally chosen to coat a support. Four factors, i.e., the mass of the NADES, pH of the samples, extraction time, and desorption time, were tested in the central composite design to select the optimal TFME conditions. Limits of detection were equal to 0.022 µg mL⁻¹ for aspartame, 0.020 µg mL⁻¹ for acesulfame-K, 0.018 µg mL⁻¹ for benzoic acid, 0.026 µg mL⁻¹ for sorbic acid, 0.013 µg mL⁻¹ for methylparaben, and 0.011 µg mL⁻¹ for ethylparaben. Satisfactory extraction recoveries between 82% and 96% were achieved with RSDs lower than 6.1% (intra-day) and 7.4% (inter-day). The proposed ‘eutectosorbent’ presented good stability that enabled effective extractions for 16 cycles with recovery of at least 77%. The proposed NADES-TFME/HPLC-UV method is highly sensitive and selective. However, the use of a solid NADES as a sorbent, synthesized without by-products, without the need for purification, and with good stability on a support with the possibility of reusability increases the ecological benefit of this method. The greenness aspect of the method was evaluated using the Complex modified Green Analytical Procedure Index protocol and is equal to 84/100. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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12 pages, 2235 KiB

Open AccessArticle

Deep Eutectic Solvent-Based Aqueous Two-Phase Systems and Their Application in Partitioning of Phenol Compounds

by Isabela N. Souza, Lucas C. V. Rodrigues, Cleide M. F. Soares, Filipe S. Buarque, Ranyere L. Souza and Álvaro S. Lima

Molecules 2024, 29(18), 4383; https://doi.org/10.3390/molecules29184383 - 15 Sep 2024

Cited by 1 | Viewed by 829

Abstract

This work studies the partition of phenolic compounds, namely caffeic acid, syringic acid, vanillic acid, ferulic acid, and vanillin, in aqueous two-phase systems (ATPSs) formed by acetonitrile and deep eutectic solvents (DESs) based on choline chloride ([Ch]Cl) and carbohydrates (sucrose, d-glucose, d-mannose, arabinose, and d-xylose). The binodal curves built at 25 °C and 0.1 MPa using DES were compared with ATPS composed of [Ch]Cl and the same carbohydrates. The ability to form ATPS depends on the number and kind of hydroxyl groups in DES’s hydrogen-bond donor compound (carbohydrates). ATPS based on DES showed biphasic regions larger than the systems based on [Ch]Cl and carbohydrates alone due to the larger hydrophilicity of DES. The ATPS were used to study the partition of the phenolic compounds. For all the systems, the biomolecules preferentially partitioned to the acetonitrile-rich phase (K > 1), and the best recovery in the top phase ranged between 53.36% (caffeic acid) and 90.09% (vanillin). According to the remarkable results, DES-based ATPS can selectively separate ferulic acid and vanillin for the top phase and syringic, caffeic, and vanillic acids for the bottom phase, achieving a selectivity higher than two. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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19 pages, 7028 KiB

Open AccessArticle

Characterization of Camphene- and Fenchol-Based Hydrophobic Eutectic Solvents and Their Application in Aldehyde Extraction

by Alexander Kaufmann, Lars Häcker, Jacob Michael Mayer, Hansjörg Weber and Marlene Kienberger

Molecules 2024, 29(17), 4232; https://doi.org/10.3390/molecules29174232 - 6 Sep 2024

Viewed by 641

Abstract

Binary terpenoid-based eutectic systems consisting of the natural substances camphene (CA), fenchol (FE), thymol (TH), menthol (ME), dodecanoic acid (DA), and 1-dodecanol (DO) are synthesized and screened for their Solid–Liquid Equilibrium (SLE) and eutectic compositions. Out of nine eutectic systems, 13 solvent compositions at eutectic points and next to them, in addition to the reference solvent, TH:ME, are synthesized and applied for the solvent extraction of the aromatic aldehydes vanillin (VAN), syringaldehyde (SYR), and p-hydroxybenzaldehyde (HYD) from an acidic aqueous model solution. The extraction efficiency is determined from aldehyde concentrations measured by High-Performance Liquid Chromatography (HPLC), taking into consideration mutual solubility measured by Karl Fischer titration (KF) and a Total Organic Carbon-analysis (TOC). Physicochemical properties, such as the density, viscosity, and stability of the solvents, are evaluated and discussed. Additionally, ¹H-NMR measurements are performed to verify hydrogen bonding present in some of the solvents. The results show that all synthesized eutectic systems have a strong hydrophobic character with a maximum water saturation of ≤2.21 vol.% and solvent losses of ≤0.12 vol.% per extraction step. The hydrophobic eutectic solvents based on CA exhibit lower viscosities, lower mutual solubility, and lower extraction efficiency for the aromatic aldehydes when compared with FE-based solvents. The highest extraction efficiencies for VAN (>95%) and for SYR (>93%) at an extraction efficiency of 92.61% for HYD are achieved by the reference solvent TH:ME (50:50 mol.%). With an extraction efficiency of 93.08%, HYD is most preferably extracted by the FE–DO-solvent (80:20 mol.%), where the extraction efficiencies for VAN and SYR reach their maximum at 93.37% and 90.75%, respectively. The drawbacks of the high viscosities of 34.741 mPas of the TH:ME solvent and 31.801 mPas of the FE–DO solvent can be overcome by the CA–TH solvent, which has a viscosity of 3.436 mPas, while exhibiting extraction efficiencies of 71.92% for HYD, >95% for VAN, and >93% for SYR, respectively. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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11 pages, 1522 KiB

Open AccessArticle

Deep Eutectic Solvent + Water System in Carbon Dioxide Absorption

by Jing Fan, Xin Zhang, Nan He, Fenhong Song and Hongwei Qu

Molecules 2024, 29(15), 3579; https://doi.org/10.3390/molecules29153579 - 29 Jul 2024

Viewed by 899

Abstract

In the present work, deep eutectic solvents (DESs) were synthesized in a one-step process by heating the hydrogen bond acceptors (HBAs) tetrabutylammonium bromide and tetrabutylphosphonium bromide, along with two hydrogen bond donors (HBDs) ethanolamine and N-methyldiethanolamine, which were mixed in certain molar ratios. This mixture was then mixed with water to form a DES + water system. The densities of the prepared DES + water systems were successfully measured using the U-tube oscillation method under atmospheric pressure over a temperature range of 293.15–363.15 K. The CO₂ trapping capacity of the DES + water systems was investigated using the isovolumetric saturation technique at pressures ranging from 0.1 MPa to 1 MPa and temperatures ranging from 303.15 K to 323.15 K. A semi-empirical model was employed to fit the experimental CO₂ solubility data, and the deviations between the experimental and fitted values were calculated. At a temperature of 303.15 K and a pressure of 100 kPa, the CO₂ solubilities in the DES + water systems of TBAB and MEA, with molar ratios of 1:8, 1:9, and 1:10, were measured to be 0.1430 g/g, 0.1479 g/g, and 0.1540 g/g, respectively. Finally, it was concluded that the DES + water systems had a superior CO₂ capture capacity compared to the 30% aqueous monoethanolamine solution commonly used in industry, indicating the potential of DES + water systems for CO₂ capture. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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21 pages, 3087 KiB

Open AccessArticle

Synthesis and Properties of Hydrophilic and Hydrophobic Deep Eutectic Solvents via Heating-Stirring and Ultrasound

by María Isabel Martín, Irene García-Díaz, María Lourdes Rodríguez, María Concepción Gutiérrez, Francisco del Monte and Félix A. López

Molecules 2024, 29(13), 3089; https://doi.org/10.3390/molecules29133089 - 28 Jun 2024

Viewed by 1142

Abstract

Deep eutectic solvents (DESs) have emerged as a greener alternative to other more polluting traditional solvents and have attracted a lot of interest in the last two decades. The DESs are less toxic dissolvents and have a lower environmental footprint. This paper presents an alternative synthesis method to the classical heating–stirring method. The ultrasound method is one of the most promising synthesis methods for DESs in terms of yield and energy efficiency. Therefore, the ultrasound synthesis method was studied to obtain hydrophobic (Aliquat 336:L-Menthol (3:7); Lidocaine:Decanoic acid (1:2)) and hydrophilic DESs based on choline chloride, urea, ethylene glycol and oxalic acid. The physical characterization of DESs via comparison of Fourier transform infrared (FTIR) spectra showed no difference between the DESs obtained by heating–stirring and ultrasound synthesis methods. The study and comparison of all the prepared DESs were carried out via nuclear magnetic resonance spectroscopy (NMR). The density and viscosity properties of DESs were evaluated. The density values were similar for both synthesis methods. However, differences in viscosity values were detected due to the presence of some water in hygroscopic DESs. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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16 pages, 8015 KiB

Open AccessArticle

Sustainable and Biomimetic Methodology for Extraction of High-Value-Added Compounds in Almond Hulls

by Gabriela Cremasco, Adam T. Sutton, Cristiano S. Funari, Dario R. Arrua, Kelly J. Dussan, Emily F. Hilder, Vanderlan S. Bolzani and Daniel Rinaldo

Molecules 2024, 29(13), 3034; https://doi.org/10.3390/molecules29133034 - 26 Jun 2024

Viewed by 1128

Abstract

Almond trees are the most cultivated nut tree in the world. The production of almonds generates large amounts of by-products, much of which goes unused. Herein, this study aimed to develop a green chemistry approach to identify and extract potentially valuable compounds from almond by-products. Initially, a screening was performed with 10 different Natural Deep Eutectic Solvents (NADESs). The mixture lactic acid/glycerol, with a molar ratio 1:1 (1:50 plant material to NADES (w/v) with 20% v/v of water) was identified as the best extraction solvent for catechin, caffeoylquinic acid, and condensed tannins in almond hulls. Subsequently, a method was optimized by a Design of Experiment (DoE) protocol using a miniaturized extraction technique, Microwave-Assisted Extraction (MAE), in conjunction with the chosen NADESs. The optimal conditions were found to be 70 °C with 15 min irradiation time. The optimal extraction conditions determined by the DoE were confirmed experimentally and compared to methods already established in the literature. With these conditions, the extraction of metabolites was 2.4 times higher, according to the increase in total peak area, than the established literature methods used. Additionally, by applying the multiparameter Analytical Greenness Metric (AGREE) and Green Analytical Process Index (GAPI) metrics, it was possible to conclude that the developed method was greener than the established literature methods as it includes various principles of green analytical chemistry. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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14 pages, 6590 KiB

Open AccessArticle

Natural Deep Eutectic Solvents as Rust Removal Agents from Lithic and Cellulosic Substrates

by Francesco Gabriele, Cinzia Casieri and Nicoletta Spreti

Molecules 2024, 29(3), 624; https://doi.org/10.3390/molecules29030624 - 28 Jan 2024

Cited by 1 | Viewed by 1624

Abstract

The peculiar physicochemical features of deep eutectic solvents (DESs), in particular their tunability, make them ideal media for various applications. Despite their ability to solubilize metal oxides, their use as rust removers from valuable substrates has not yet been thoroughly investigated. In this study, we chose three known DESs, consisting of choline chloride and acetic, oxalic or citric acid for evaluating their ability to remove corrosion products from a cellulose-based material as linen fabric and two different lithotypes, as travertine and granite. The artificial staining was achieved by placing a rusty iron grid on their surfaces. The DESs were applied by means of cellulose poultice on the linen fabrics, while on the rusted stone surfaces with a cotton swab. Macro- and microscopic observations, colorimetry and SEM/EDS analysis were employed to ascertain the cleaning effectiveness and the absence of side effects on the samples after treatment. Oxalic acid-based DES was capable of removing rust stains from both stone and cellulose-based samples, while choline chloride/citric acid DES was effective only on stone specimens. The results suggest a new practical application of DESs for the elimination of rust from lithic and cellulosic substrates of precious and artistic value. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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13 pages, 2031 KiB

Open AccessArticle

Preparation and Characterization of Zinc(II)-Based Lewis/Brønsted Acidic Deep Eutectic Solvents

by Chiara Pelosi, Aldo Quaranta, Marco Rollo, Elisa Martinelli, Celia Duce, Gianluca Ciancaleoni and Luca Bernazzani

Molecules 2023, 28(24), 8054; https://doi.org/10.3390/molecules28248054 - 12 Dec 2023

Viewed by 1858

Abstract

Lewis/Brønsted acidic deep eutectic solvents (LBDESs) are a recent class of solvents that combine the two types of acidity. In some cases, this synergy leads to enhanced catalytic properties for many reactions and applications. For this reason, it is important to discover more LBDESs. In this work, we prepared and characterized four different zinc(II)-based LBDESs, mixing ZnCl₂ and various Brønsted acids: acetic, glycolic, levulinic, and formic acids. Apart from the latter, for which the corresponding DES is not thermally stable, the samples have been characterized in terms of density, viscosity, and conductivity. Notably, as zinc(II) is a diamagnetic metal, all of them are suitable for NMR spectroscopy, for example, for kinetic and mechanistic studies. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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14 pages, 2735 KiB

Open AccessArticle

Epsom Salt-Based Natural Deep Eutectic Solvent as a Drilling Fluid Additive: A Game-Changer for Shale Swelling Inhibition

by Muhammad Hammad Rasool and Maqsood Ahmad

Molecules 2023, 28(15), 5784; https://doi.org/10.3390/molecules28155784 - 31 Jul 2023

Cited by 5 | Viewed by 1601

Abstract

Shale rock swelling poses a significant challenge during drilling a well, leading to issues related to wellbore instability. Water-based mud with specific shale inhibitors is preferred over oil-based drilling mud due to its lower environmental impact. Recently, ionic liquids (ILs) have emerged as potential shale inhibitors due to their adjustable properties and strong electrostatic attraction. However, research has shown that the most commonly used class of ILs (imidazolium) in drilling mud are toxic, non-biodegradable, and expensive. Deep Eutectic Solvents (DESs), the fourth generation of ionic liquids, have been proposed as a cheaper and non-toxic alternative to ILs. However, ammonium salt-based DESs are not truly environmentally friendly. This research explores the utilization of Natural Deep Eutectic Solvent (NADES) based on Epsom salt (a naturally occurring salt) and glycerine as a drilling fluid additive. The drilling mud is prepared according to API 13B-1 standards. Various concentrations of NADES-based mud are tested for yield point, plastic viscosity, and filtration properties for both aged and non-aged samples. The linear swell meter is used to determine the percentage swelling of the NADES-based mud, and the results are compared with the swelling caused by KCl- and EMIM-Cl-based mud. FTIR analysis is conducted to understand the interaction between NADES and clay, while surface tension, d-spacing (XRD), and zeta potential are measured to comprehend the mechanism of swelling inhibition by NADES. The findings reveal that NADES improves the yield point and plastic viscosity of the mud, resulting in a 26% reduction in mudcake thickness and a 30.1% decrease in filtrate volume at a concentration of 1%. NADES achieves a significant 49.14% inhibition of swelling at the optimal concentration of 1%, attributed to its ability to modify surface activity, zeta potential of clay surfaces, and d-spacing of clay layers. Consequently, NADES emerges as a non-toxic, cost-effective, and efficient shale inhibitor that can replace ILs and DESs. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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10 pages, 2593 KiB

Open AccessCommunication

CO₂ Capture Mechanism by Deep Eutectic Solvents Formed by Choline Prolinate and Ethylene Glycol

by Mingzhe Chen and Jinming Xu

Molecules 2023, 28(14), 5461; https://doi.org/10.3390/molecules28145461 - 17 Jul 2023

Cited by 8 | Viewed by 1633

Abstract

The choline prolinate ([Ch][Pro]) as a hydrogen bond acceptor and ethylene glycol (EG) as a hydrogen bond donor are both used to synthesize the deep eutectic solvents (DESs) [Ch][Pro]-EG to capture CO₂. The CO₂ capacity of [Ch][Pro]-EG is determined, and the nuclear magnetic resonance (NMR) and infrared (IR) spectrum are used to investigate the CO₂ capture mechanism. The results indicate that CO₂ reacts with both the amino group of [Pro]⁻ anion and the hydroxyl group of EG, and the mechanism found in this work is different from that reported in the literature for the [Ch][Pro]-EG DESs. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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Review

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26 pages, 2426 KiB

Open AccessReview

Investigating Biomolecules in Deep Eutectic Solvents with Molecular Dynamics Simulations: Current State, Challenges and Future Perspectives

by Jan Philipp Bittner, Irina Smirnova and Sven Jakobtorweihen

Molecules 2024, 29(3), 703; https://doi.org/10.3390/molecules29030703 - 2 Feb 2024

Cited by 8 | Viewed by 2248

Abstract

Deep eutectic solvents (DESs) have recently gained increased attention for their potential in biotechnological applications. DESs are binary mixtures often consisting of a hydrogen bond acceptor and a hydrogen bond donor, which allows for tailoring their properties for particular applications. If produced from sustainable resources, they can provide a greener alternative to many traditional organic solvents for usage in various applications (e.g., as reaction environment, crystallization agent, or storage medium). To navigate this large design space, it is crucial to comprehend the behavior of biomolecules (e.g., enzymes, proteins, cofactors, and DNA) in DESs and the impact of their individual components. Molecular dynamics (MD) simulations offer a powerful tool for understanding thermodynamic and transport processes at the atomic level and offer insights into their fundamental phenomena, which may not be accessible through experiments. While the experimental investigation of DESs for various biotechnological applications is well progressed, a thorough investigation of biomolecules in DESs via MD simulations has only gained popularity in recent years. Within this work, we aim to provide an overview of the current state of modeling biomolecules with MD simulations in DESs and discuss future directions with a focus for optimizing the molecular simulations and increasing our fundamental knowledge. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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Other

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17 pages, 2026 KiB

Open AccessOpinion

Electrodeposition in Deep Eutectic Solvents: The “Obvious”, the “Unexpected” and the “Wonders”

by Thomas Doneux, Alassane Sorgho, Fousséni Soma, Quentin Rayée and Moussa Bougouma

Molecules 2024, 29(14), 3439; https://doi.org/10.3390/molecules29143439 - 22 Jul 2024

Viewed by 758

Abstract

Deep eutectic solvents (DESs) are attracting considerable attention as non-conventional media for electrodeposition processes. This opinion contribution discusses the debated nature and definition of these solvents as well as some practical considerations of relevance when performing electrodeposition studies in DESs. Using a few illustrative case studies, it is shown that speciation is a key factor determining the electrochemical behaviour of chemical elements in different DESs, and that accounting for the speciation strong similarities can often be found with more conventional or more documented solvents. The need for thermodynamic data is emphasised and it is suggested to expand the composition range of these solvents beyond fixed ratios between the components to exploit the full potentialities of DESs. Full article

(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)

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