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

Deadline for manuscript submissions: closed (31 August 2022) | Viewed by 29367

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Dr. Reza Haghbakhsh

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1. Department of Chemical Engineering, Faculty of Engineering, University of Isfahan, Isfahan, Iran
2. Department of Chemistry, School of Science and Technology, NOVA University Lisbon, Caparica, Portugal
Interests: green solvents; green chemistry; deep eutectic solvents; ionic liquids; applied thermodynamics; phase equilibria; physical properties; energy
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Dr. Sona Raeissi

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Guest Editor

School of Chemical and Petroleum Engineering, Shiraz University, Shiraz, Iran
Interests: green solvents; green chemistry; deep eutectic solvents; ionic liquids; supercritical fluids; phase equilibria; physical properties; environmental engineering

Dr. Rita Craveiro

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Guest Editor

Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Lisboa, Portugal
Interests: DES; NADES; thermophysical studies biocatalysis; gas absorption; supercritical fluids; green chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In previous decades, industries have mostly developed at the cost of environmental neglect, resulting in numerous environmental issues and, ultimately, a distressing crisis to the planet. Therefore, in the 21^st century, governments and world organizations are attempting to legislate sustainable development laws for industrial advances. “Green chemistry”, as a rather novel field of chemistry and chemical engineering, is one of the key routes to assist researchers in sustainable development. Among the most valuable assets of green chemistry, “green solvents” are the primary candidates to replace the workhorses of industries, i.e., the conventional harmful solvents. In recent decades, green solvents have been studied intensively by scientists and researchers, and the number of published articles has been growing exponentially. The most important green solvents, such as supercritical fluids, ionic liquids, and deep eutectic solvents, have been investigated in various fields and for numerous applications; yet much remains unknown, and there is great room for further investigations into this class of solvents.

This Special Issue aims to publish the most recent advances in the interdisciplinary area of green solvents. All research and review articles dealing with fundamental as well as application-based studies on green solvents are welcome, including, for example, theoretical studies at a molecular scale, thermodynamic investigations covering phase behavior and pure and mixture physical properties, as well as industrially minded endeavors such as separations, reactions, catalysis, chemical processes, bioprocesses, food science, pharmaceuticals, environmental engineering, and innovative techniques.

Dr. Reza Haghbakhsh
Dr. Sona Raeissi
Dr. Rita Craveiro
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

green solvents (deep eutectic solvents, ionic liquids, supercritical fluids)
theoretical and thermodynamic investigations
green processes
sustainable separations
reactions and catalysis
environmental chemistry
bioproducts and biofuels
sustainable foods and pharmaceuticals

Published Papers (13 papers)

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Editorial

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3 pages, 203 KiB

Open AccessEditorial

Editorial for Special Issue: “Recent Advances in Green Solvents”

by Reza Haghbakhsh, Sona Raeissi and Rita Craveiro

Molecules 2023, 28(16), 5983; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28165983 - 10 Aug 2023

Viewed by 657

Abstract

Today, environmental conservation is one of the most urgent targets [...] Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

Research

Jump to: Editorial

14 pages, 5341 KiB

Open AccessArticle

Biodiesel Purification by Solvent-Aided Crystallization Using 2-Methyltetrahydrofuran

by Wan Nur Aisyah Wan Osman, Nur Athirah Izzati Badrol and Shafirah Samsuri

Molecules 2023, 28(3), 1512; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28031512 - 3 Feb 2023

Cited by 3 | Viewed by 1596

Abstract

The previous biodiesel purification by Solvent-Aided Crystallization (SAC) using 1-butanol as assisting agent and parameters for SAC were optimized such as coolant temperature, cooling time and stirring speed. Meanwhile, 2-Methyltetrahydrofuran (2-MeTHF) was selected as an alternative to previous organic solvents for this study. In this context, it is used to replace solvent 1-butanol from a conducted previous study. This study also focuses on the technological improvements in the purification of biodiesel via SAC as well as to produce an even higher purity of biodiesel. Experimental works on the transesterification process to produce crude biodiesel were performed and SAC was carried out to purify the crude biodiesel. The crude biodiesel content was analyzed by using Gas Chromatography–Mass Spectrometry (GC-MS) and Differential Scanning Calorimetry (DSC) to measure the composition of Fatty Acid Methyl Esters (FAME) present. The optimum value to yield the highest purity of FAME for parameters coolant temperature, cooling time, and stirring speed is −4 °C, 10 min and 210 rpm, respectively. It can be concluded that the assisting solvent 2-MeTHF has a significant effect on the process parameters to produce purified biodiesel according to the standard requirement. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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14 pages, 1361 KiB

Open AccessArticle

Prediction of pH Value of Aqueous Acidic and Basic Deep Eutectic Solvent Using COSMO-RS σ Profiles’ Molecular Descriptors

by Manuela Panić, Mia Radović, Marina Cvjetko Bubalo, Kristina Radošević, Marko Rogošić, João A. P. Coutinho, Ivana Radojčić Redovniković and Ana Jurinjak Tušek

Molecules 2022, 27(14), 4489; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27144489 - 13 Jul 2022

Cited by 15 | Viewed by 2194

Abstract

The aim of this work was to develop a simple and easy-to-apply model to predict the pH values of deep eutectic solvents (DESs) over a wide range of pH values that can be used in daily work. For this purpose, the pH values of 38 different DESs were measured (ranging from 0.36 to 9.31) and mathematically interpreted. To develop mathematical models, DESs were first numerically described using σ profiles generated with the COSMOtherm software. After the DESs’ description, the following models were used: (i) multiple linear regression (MLR), (ii) piecewise linear regression (PLR), and (iii) artificial neural networks (ANNs) to link the experimental values with the descriptors. Both PLR and ANN were found to be applicable to predict the pH values of DESs with a very high goodness of fit (R²_{independent validation} > 0.8600). Due to the good mathematical correlation of the experimental and predicted values, the σ profile generated with COSMOtherm could be used as a DES molecular descriptor for the prediction of their pH values. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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12 pages, 4526 KiB

Open AccessArticle

Neutron Total Scattering Investigation of the Dissolution Mechanism of Trehalose in Alkali/Urea Aqueous Solution

by Changli Ma, Taisen Zuo, Zehua Han, Yuqing Li, Sabrina Gärtner, Huaican Chen, Wen Yin, Charles C. Han and He Cheng

Molecules 2022, 27(11), 3395; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27113395 - 25 May 2022

Cited by 3 | Viewed by 1528

Abstract

The atomic picture of cellulose dissolution in alkali/urea aqueous solution is still not clear. To reveal it, we use trehalose as the model molecule and total scattering as the main tool. Three kinds of alkali solution, i.e., LiOH, NaOH and KOH are compared. The most probable all-atom structures of the solution are thus obtained. The hydration shell of trehalose has a layered structure. The smaller alkali ions can penetrate into the glucose rings around oxygen atoms to form the first hydration layer. The larger urea molecules interact with hydroxide groups to form complexations. Then, the electronegative complexation can form the second hydration layer around alkali ions via electrostatic interaction. Therefore, the solubility of alkali aqueous solution for cellulose decreases with the alkali cation radius, i.e., LiOH > NaOH > KOH. Our findings are helpful for designing better green solvents for cellulose. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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11 pages, 2357 KiB

Open AccessArticle

Enhanced Extraction Efficiency of Flavonoids from Pyrus ussuriensis Leaves with Deep Eutectic Solvents

by Jong Woo Lee, Hye Yoon Park and Junseong Park

Molecules 2022, 27(9), 2798; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27092798 - 28 Apr 2022

Cited by 8 | Viewed by 2020

Abstract

In this study, deep eutectic solvents (DESs) were synthesized using different ratios of choline chloride (CC) and dicarboxylic acids, and their eutectic temperatures were determined. The DES synthesized using CC and glutaric acid (GA), which showed a higher extraction efficiency than conventional solvents, was used for the extraction of flavonoid components from Pyrus ussuriensis leaves (PUL), and the extraction efficiency was evaluated using the response surface methodology. The flavonoid components rutin, hyperoside, and isoquercitrin were identified through high-performance liquid chromatography (HPLC), equipped with a Waters 2996 PDA detector, and HPLC mass spectrometry (LC-MS/MS) analyses. The optimum extraction was achieved at a temperature of 30 °C using DES in a concentration of 30.85 wt.% at a stirring speed of 1113 rpm and an extraction time of 1 h. The corresponding flavonoid content was 217.56 μg/mL. The results were verified by performing three reproducibility experiments, and a high significance, with a confidence range of 95%, was achieved. In addition, the PUL extracts exhibited appreciable antioxidant activity. The results showed that the extraction process using the DES based on CC and GA in a 1:1 molar ratio could effectively improve the yield of flavonoids from PUL. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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16 pages, 24862 KiB

Open AccessArticle

Copper-Free Halodediazoniation of Arenediazonium Tetrafluoroborates in Deep Eutectic Solvents-like Mixtures

by Giovanni Ghigo, Matteo Bonomo, Achille Antenucci, Chiara Reviglio and Stefano Dughera

Molecules 2022, 27(6), 1909; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27061909 - 15 Mar 2022

Cited by 9 | Viewed by 3081

Abstract

Deep Eutectic Solvent (DES)-like mixtures, based on glycerol and different halide organic and inorganic salts, are successfully exploited as new media in copper-free halodediazoniation of arenediazonium salts. The reactions are carried out in absence of metal-based catalysts, at room temperature and in a short time. Pure target products are obtained without the need for chromatographic separation. The solvents are fully characterized, and a computational study is presented aiming to understand the reaction mechanism. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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12 pages, 2135 KiB

Open AccessArticle

Hydrothermal CO₂ Reduction by Glucose as Reducing Agent and Metals and Metal Oxides as Catalysts

by Maira I. Chinchilla, Fidel A. Mato, Ángel Martín and María D. Bermejo

Molecules 2022, 27(5), 1652; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27051652 - 2 Mar 2022

Cited by 9 | Viewed by 2769

Abstract

High-temperature water reactions to reduce carbon dioxide were carried out by using an organic reductant and a series of metals and metal oxides as catalysts, as well as activated carbon (C). As CO₂ source, sodium bicarbonate and ammonium carbamate were used. Glucose was the reductant. Cu, Ni, Pd/C 5%, Ru/C 5%, C, Fe₂O₃ and Fe₃O₄ were the catalysts tested. The products of CO₂ reduction were formic acid and other subproducts from sugar hydrolysis such as acetic acid and lactic acid. Reactions with sodium bicarbonate reached higher yields of formic acid in comparison to ammonium carbamate reactions. Higher yields of formic acid (53% and 52%) were obtained by using C and Fe₃O₄ as catalysts and sodium bicarbonate as carbon source. Reactions with ammonium carbamate achieved a yield of formic acid up to 25% by using Fe₃O₄ as catalyst. The origin of the carbon that forms formic acid was investigated by using NaH¹³CO₃ as carbon source. Depending on the catalyst, the fraction of formic acid coming from the reduction of the isotope of sodium bicarbonate varied from 32 to 81%. This fraction decreased in the following order: Pd/C 5% > Ru/C 5% > Ni > Cu > C ≈ Fe₂O₃ > Fe₃O₄. Full article

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17 pages, 2392 KiB

Open AccessArticle

Deep Eutectic Solvents as Phase Change Materials in Solar Thermal Power Plants: Energy and Exergy Analyses

by Hamed Peyrovedin, Reza Haghbakhsh, Ana Rita C. Duarte and Alireza Shariati

Molecules 2022, 27(4), 1427; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27041427 - 20 Feb 2022

Cited by 5 | Viewed by 1861

Abstract

Nowadays, producing energy from solar thermal power plants based on organic Rankine cycles coupled with phase change material has attracted the attention of researchers. Obviously, in such solar plants, the physical properties of the utilized phase change material (PCM) play important roles in the amounts of generated power and the efficiencies of the plant. Therefore, to choose the best PCM, various factors must be taken into account. In addition, considering the physical properties of the candidate PCM, the issue of environmental sustainability should also be considered when making the selection. Deep eutectic solvents (DESs) are novel green solvents, which, in addition to having various favorable characteristics, are environmentally sustainable. Accordingly, in this work, the feasibility of using seven different deep eutectic solvents as the PCMs of solar thermal power plants with organic Rankine cycles was investigated. By applying exergy and energy analyses, the performances of each were compared to paraffin, which is a conventional PCM. According to the achieved results, most of the investigated “DES cycles” produce more power than the conventional cycle using paraffin as its PCM. Furthermore, lower amounts of the PCM are required when paraffin is replaced by a DES at the same operational conditions. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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19 pages, 1917 KiB

Open AccessArticle

The Response Surface Optimization of Supercritical CO₂ Modified with Ethanol Extraction of p-Anisic Acid from Acacia mearnsii Flowers and Mathematical Modeling of the Mass Transfer

by Graciane Fabiela da Silva, Edgar Teixeira de Souza Júnior, Rafael Nolibos Almeida, Ana Luisa Butelli Fianco, Alexandre Timm do Espirito Santo, Aline Machado Lucas, Rubem Mário Figueiró Vargas and Eduardo Cassel

Molecules 2022, 27(3), 970; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030970 - 31 Jan 2022

Cited by 3 | Viewed by 2835

Abstract

A widely disseminated native species from Australia, Acacia mearnsii, which is mainly cultivated in Brazil and South Africa, represents a rich source of natural tannins used in the tanning process. Many flowers of the Acacia species are used as sources of compounds of interest for the cosmetic industry, such as phenolic compounds. In this study, supercritical fluid extraction was used to obtain non-volatile compounds from A. mearnsii flowers for the first time. The extract showed antimicrobial activity and the presence of p-anisic acid, a substance with industrial and pharmaceutical applications. The fractionation of the extract was performed using a chromatographic column and the fraction containing p-anisic acid presented better minimum inhibitory concentration (MIC) results than the crude extract. Thus, the extraction process was optimized to maximize the p-anisic acid extraction. The response surface methodology and the Box–Behnken design was used to evaluate the pressure, temperature, the cosolvent, and the influence of the particle size on the extraction process. After the optimization process, the p-anisic acid yield was 2.51% w/w and the extraction curve was plotted as a function of time. The simulation of the extraction process was performed using the three models available in the literature. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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17 pages, 2874 KiB

Open AccessArticle

Experimental Investigation on Thermophysical Properties of Ammonium-Based Protic Ionic Liquids and Their Potential Ability towards CO₂ Capture

by Nur Hidayah Zulaikha Othman Zailani, Normawati M. Yunus, Asyraf Hanim Ab Rahim and Mohamad Azmi Bustam

Molecules 2022, 27(3), 851; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030851 - 27 Jan 2022

Cited by 7 | Viewed by 2607

Abstract

Ionic liquids, which are extensively known as low-melting-point salts, have received significant attention as the promising solvent for CO₂ capture. This work presents the synthesis, thermophysical properties and the CO₂ absorption of a series of ammonium cations coupled with carboxylate anions producing ammonium-based protic ionic liquids (PILs), namely 2-ethylhexylammonium pentanoate ([EHA][C5]), 2-ethylhexylammonium hexanoate ([EHA][C6]), 2-ethylhexylammonium heptanoate ([EHA][C7]), bis-(2-ethylhexyl)ammonium pentanoate ([BEHA][C5]), bis-(2-ethylhexyl)ammonium hexanoate ([BEHA][C6]) and bis-(2-ethylhexyl)ammonium heptanoate ([BEHA][C7]). The chemical structures of the PILs were confirmed by using Nuclear Magnetic Resonance (NMR) spectroscopy while the density (ρ) and the dynamic viscosity (η) of the PILs were determined and analyzed in a range from 293.15K up to 363.15K. The refractive index (n_D) was also measured at T = (293.15 to 333.15) K. Thermal analyses conducted via a thermogravimetric analyzer (TGA) and differential scanning calorimeter (DSC) indicated that all PILs have the thermal decomposition temperature, T_d of greater than 416K and the presence of glass transition, T_g was detected in each PIL. The CO₂ absorption of the PILs was studied up to 29 bar at 298.15 K and the experimental results showed that [BEHA][C7] had the highest CO₂ absorption with 0.78 mol at 29 bar. The CO₂ absorption values increase in the order of [C5] < [C6] < [C7] anion regardless of the nature of the cation. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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22 pages, 4121 KiB

Open AccessArticle

Novel Binary Mixtures of Alkanolamine Based Deep Eutectic Solvents with Water—Thermodynamic Calculation and Correlation of Crucial Physicochemical Properties

by Bartosz Nowosielski, Marzena Jamrógiewicz, Justyna Łuczak and Dorota Warmińska

Molecules 2022, 27(3), 788; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030788 - 25 Jan 2022

Cited by 10 | Viewed by 2653

Abstract

This paper demonstrates the assessment of physicochemical and thermodynamic properties of aqueous solutions of novel deep eutectic solvent (DES) built of tetrabutylammonium chloride and 3-amino-1-propanol or tetrabutylammonium bromide and 3-amino-1-propanol or 2-(methylamino)ethanol or 2-(butylamino)ethanol. Densities, speeds of sound, refractive indices, and viscosities for both pure and aqueous mixtures of DES were investigated over the entire range of compositions at atmospheric pressure and T = (293.15 ‒ 313.15) K. It was concluded that the experimental data were successfully fitted using the Jouyban–Acree model with respect to the concentration. Obtained results showed that this mathematical equation is an accurate correlation for the prediction of aqueous DES properties. Key physicochemical properties of the mixtures—such as excess molar volumes, excess isentropic compressibilities, deviations in viscosity, and deviations in refractive indices—were calculated and correlated by the Redlich–Kister equation with temperature-dependent parameters. The non-ideal behavior of the studied systems were also evaluated by using the Prigogine−Flory−Patterson theory and the results were interpreted in terms of interactions between the mixture components. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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17 pages, 2881 KiB

Open AccessArticle

Adsorption of N,N,N′,N′-Tetraoctyl Diglycolamide on Hypercrosslinked Polysterene from a Supercritical Carbon Dioxide Medium

by Mikhail Kostenko and Olga Parenago

Molecules 2022, 27(1), 31; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010031 - 22 Dec 2021

Cited by 4 | Viewed by 2077

Abstract

The work considers for the first time the preparation of sorbents based on hypercrosslinked polysterene (HCP) and chelating agent N,N,N′,N′-tetraoctyl diglycolamide (TODGA) by impregnation in the supercritical (SC) CO₂ medium. Such sorbents can be applied for further isolation and separation of lanthanides, actinides and other metals. They are usually prepared by impregnation in toxic organic solvents (e.g., methanol, dichloromethane). Our study shows that application of SC CO₂ instead of organic solvents can significantly speed up the impregnation, perfom it in one stage and make the process more eco-friendly. At the same time, the obtained sorbents are close in their parameters to the classical ones. This article presents the results of measuring the TODGA adsorption isotherms on two HCP sorbents (MN202 and MN270) on a wide range of SC fluid parameters. Adsorption measurements were carried out using on-line supercritical fluid chromatography and gravimetry. Based on the sorption capacity parameter, MN202 sorbent was selected as the better carrier for TODGA. An impregnation temperature increase within the range 313–343 K in isochoric conditions (ρ = 0.780 g/mL) reduces the maximum of TODGA adsorption from ~0.68 mmol/g to ~0.49 mmol/g. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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10 pages, 932 KiB

Open AccessArticle

Ionic Liquid Extraction Behavior of Cr(VI) Absorbed on Humic Acid–Vermiculite

by Hsin-Liang Huang, P.C. Lin, H.T. Wang, Hsin-Hung Huang and Chao-Ho Wu

Molecules 2021, 26(24), 7478; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247478 - 10 Dec 2021

Cited by 2 | Viewed by 1964

Abstract

Cr(VI) can be released into soil as a result of mining, electroplating, and smelting operations. Due to the high toxicity of Cr(VI), its removal is necessary in order to protect ecosystems. Vermiculite is applied in situations where there is a high degree of metal pollution, as it is helpful during the remediation process due to its high cation exchange capacity. The Cr(VI) contained in the vermiculite should be extracted in order to recover it and to reduce the impact on the environment. In this work, adsorption equilibrium data for Cr(VI) in a simulated sorbent for soil remediation (a mixture that included both humic acid (HA) and vermiculite) were a good fit with the Langmuir isotherm model. The simulated sorbent for soil remediation was a favorable sorbent for Cr(VI) when it was in the test soil. An ionic liquid, [C₄mim]Cl (1-butyl-3-methylimidazolium chloride), was studied to determine its efficiency in extracting Cr(VI) from the Cr- contaminated simulated sorbent in soil remediation. At 298 K and within 30 min, approximately 33.48 ± 0.79% of Cr(VI) in the simulated sorbent in soil remediation was extracted into [C₄mim]Cl. Using FTIR spectroscopy, the absorbance intensities of the bands at 1032 and 1010 cm⁻¹, which were attributed to C-O bond stretching in the polysaccharides of HA, were used to detect the changes in HA in the Cr-contaminated simulated sorbent for soil remediation before and after extraction. The results showed that Cr(VI) that has been absorbed on HA can be extracted into [C₄mim]Cl. Using ¹H NMR, it was observed that the 1-methylimizadole of [C₄mim] Cl played an important role in the extraction of Cr(VI), which bonded with HA on vermiculite and was able to be transformed into the [C₄mim]Cl phase. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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