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16 pages, 5366 KiB

Open AccessArticle

Solubility and Stability of Carotenoids in Ammonium- and Phosphonium-Based Ionic Liquids: Effect of Solvent Nature, Temperature and Water

by Wanting Cheng, Feng Xian, Zhanluo Zhou, Kun Hu and Jing Gao

Molecules 2023, 28(8), 3618; https://doi.org/10.3390/molecules28083618 - 21 Apr 2023

Cited by 5 | Viewed by 3209

Abstract

Ionic liquids (ILs) have arisen as alternatives to organic solvents and been used in natural pigment extraction in recent decades. However, the solubility and stability of carotenoids in phosphonium- and ammonium-based ILs are insufficiently explored. In this work, the physicochemical properties of the [...] Read more.

Ionic liquids (ILs) have arisen as alternatives to organic solvents and been used in natural pigment extraction in recent decades. However, the solubility and stability of carotenoids in phosphonium- and ammonium-based ILs are insufficiently explored. In this work, the physicochemical properties of the ILs, and the dissolution behavior and storage stability of three carotenoids (astaxanthin, β-carotene, and lutein) in the IL aqueous solution were investigated. The results showed that the solubility of the carotenoids in the acidic IL solution is higher than that in the alkaline IL solution, and the optimal pH is about 6. The solubility of astaxanthin (40 mg/100 g), β-carotene (105 mg/100 g), and lutein (5250 mg/100 g) was the highest in tributyloctylphosphonium chloride ([P₄₄₄₈]Cl) due to the van der Waals forces with [P₄₄₄₈]⁺ and hydrogen bonding with Cl⁻. A high temperature was beneficial to improve the solubility, but it can reduce the storage stability. Water has no significant effect on the carotenoid stability, but a high water content decreases the carotenoid solubility. A IL water content of 10–20%, an extraction temperature of 338.15 K, and a storage temperature of less than 298.15 K are beneficial for reducing the IL viscosity, improving carotenoid solubility, and maintaining good stability. Moreover, a linear correlation was found between the color parameters and carotenoid contents. This study provides some guidance for screening suitable solvents for carotenoid extraction and storage. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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17 pages, 7144 KiB

Open AccessArticle

Screening of Ionic Liquids against Bamboo Mildew and Its Inhibition Mechanism

by Chunlin Liu, Shiqin Chen, Yingying Shan, Chungui Du, Jiawei Zhu, Qichao Bao, Yuran Shao, Wenxiu Yin, Fei Yang, Ying Ran and Yuting Wang

Molecules 2023, 28(8), 3432; https://doi.org/10.3390/molecules28083432 - 13 Apr 2023

Cited by 1 | Viewed by 1651

Abstract

Ionic liquids are a class of organic molten salts that consist entirely of cations and anions. They are characterized by their low vapor pressure, low viscosity, low toxicity, high thermal stability, and strong antifungal potential. In this study, the inhibitory performance of ionic [...] Read more.

Ionic liquids are a class of organic molten salts that consist entirely of cations and anions. They are characterized by their low vapor pressure, low viscosity, low toxicity, high thermal stability, and strong antifungal potential. In this study, the inhibitory performance of ionic liquid cations against Penicillium citrinum, Trichoderma viride, and Aspergillus niger was investigated, along with the mechanism of cell membrane disruption. The Oxford cup method, SEM, and TEM were employed to examine the extent of damage and the specific site of action of ionic liquids on the mycelium and cell structure of these fungi. The results showed that 1-decyl-3-methylimidazole had a strong inhibitory effect on TV; benzyldimethyldodecylammonium chloride had a weak inhibitory effect on PC, TV, AN, and a mixed culture; while dodecylpyridinium chloride exhibited significant inhibitory effects on PC, TV, AN, and Mix, with more prominent effects observed on AN and Mix, exhibiting MIC values of 5.37 mg/mL, 5.05 mg/mL, 5.10 mg/mL, and 5.23 mg/mL, respectively. The mycelium of the mildews showed drying, partial loss, distortion, and uneven thickness. The cell structure showed separation of the plasma wall. The absorbance of the extracellular fluid of PC and TV reached the maximum after 30 min, while that of AN reached the maximum after 60 min. The pH of the extracellular fluid decreased initially and then increased within 60 min, followed by a continuous decrease. These findings provide important insights for the application of ionic liquid antifungal agents in bamboo, medicine, and food. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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22 pages, 5338 KiB

Open AccessArticle

Lignosulfonate-Based Ionic Liquids as Asphaltene Dispersants

by Ariff Mahtar, Aliyu Adebayo Sulaimon and Cecilia Devi Wilfred

Molecules 2023, 28(8), 3390; https://doi.org/10.3390/molecules28083390 - 12 Apr 2023

Cited by 2 | Viewed by 2017

Abstract

Asphaltenes are recognized as being troublesome from upstream to downstream in the oil industry due to their tendency to precipitate and self-associate. Their extraction from asphaltenic crude oil for a cost-effective refining process is a crucial and critical challenge in the oil and [...] Read more.

Asphaltenes are recognized as being troublesome from upstream to downstream in the oil industry due to their tendency to precipitate and self-associate. Their extraction from asphaltenic crude oil for a cost-effective refining process is a crucial and critical challenge in the oil and gas sector. Lignosulfonate (LS), as a by-product of the wood pulping process in the papermaking industry, is a highly available and underutilized feedstock. This study aimed to synthesize novel LS-based ionic liquids (ILs) by reacting lignosulfonate acid sodium salt [Na]₂[LS] with different alkyl chains of piperidinium chloride for asphaltene dispersion. The synthesized ILs, 1-hexyl-1-methyl-piperidinium lignosulfonate [C₆C₁Pip]₂[LS], 1-octyl-1-methyl-piperidinium lignosulfonate [C₈C₁Pip]₂[LS], 1-dodecyl-1-methyl-piperidinium lignosulfonate [C₁₂C₁Pip]₂[LS] and 1-hexadecyl-1-methyl-piperidinium lignosulfonate [C₁₆C₁Pip]₂[LS] were characterized using FTIR-ATR and ¹H NMR for functional groups and structural confirmation. The ILs depicted high thermal stability because of the presence of a long side alkyl chain and piperidinium cation following thermogravimetric analysis (TGA). Asphaltene dispersion indices (%) of ILs were tested by varying contact time, temperature and ILs concentration. The obtained indices were high for all ILs, with a dispersion index of more than 91.2% [C₁₆C₁Pip]₂[LS], representing the highest dispersion at 50,000 ppm. It was able to lower asphaltene particle size diameter from 51 nm to 11 nm. The kinetic data of [C₁₆C₁Pip]₂[LS] were consistent with the pseudo-second-order kinetic model. The dispersion index (%), asphaltene particle growth and the kinetic model agreed with the molecular modeling studies of the HOMO–LUMO energy of IL holds. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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17 pages, 3471 KiB

Open AccessArticle

Thermoresponsive Ionic Liquid with Different Cation–Anion Pairs as Draw Solutes in Forward Osmosis

by DaEun Yang and Hyo Kang

Molecules 2022, 27(24), 8869; https://doi.org/10.3390/molecules27248869 - 13 Dec 2022

Cited by 2 | Viewed by 1544

Abstract

We synthesized various phosphonium- and ammonium-based ionic liquids (ILs), using benzenesulfonate (BS) and 4-methylbenzenesulfonate (MBS) to establish the criteria for designing an ideal draw solute in a forward osmosis (FO) system. Additionally, the effects of monocationic, dicationic, and anionic species on FO performance [...] Read more.

We synthesized various phosphonium- and ammonium-based ionic liquids (ILs), using benzenesulfonate (BS) and 4-methylbenzenesulfonate (MBS) to establish the criteria for designing an ideal draw solute in a forward osmosis (FO) system. Additionally, the effects of monocationic, dicationic, and anionic species on FO performance were studied. Monocationic compounds ([P₄₄₄₄][BS], [P₄₄₄₄][MBS], [N₄₄₄₄][BS], and [N₄₄₄₄][MBS]) were obtained in one step via anion exchange. Dicationic compounds ([(P₄₄₄₄)₂][BS], [(P₄₄₄₄)₂][MBS], [(N₄₄₄₄)₂][BS], and [(N₄₄₄₄)₂][MBS]) were prepared in two steps via a Menshutkin SN₂ reaction and anion exchange. We also investigated the suitability of ILs as draw solutes for FO systems. The aqueous [P₄₄₄₄][BS], [N₄₄₄₄][BS], [N₄₄₄₄][MBS], and [(N₄₄₄₄)₂][BS] solutions did not exhibit thermoresponsive behavior. However, 20 wt% [P₄₄₄₄][MBS], [(P₄₄₄₄)₂][BS], [(P₄₄₄₄)₂][MBS], and [(N₄₄₄₄)₂][MBS] had critical temperatures of approximately 43, 33, 22, and 60 °C, respectively, enabling their recovery using temperature. An increase in IL hydrophobicity and bulkiness reduces its miscibility with water, demonstrating that it can be used to tune its thermoresponsive properties. Moreover, the FO performance of 20 wt% aqueous [(P₄₄₄₄)₂][MBS] solution was tested for water flux and found to be approximately 10.58 LMH with the active layer facing the draw solution mode and 9.40 LMH with the active layer facing the feed solution. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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13 pages, 2296 KiB

Open AccessArticle

Structural, Thermal, and Storage Stability of Rapana Thomasiana Hemocyanin in the Presence of Cholinium-Amino Acid-Based Ionic Liquids

by Maya Guncheva, Krassimira Idakieva, Svetla Todinova, Denitsa Yancheva, Tsvetelina Paunova-Krasteva, Paula Ossowicz and Ewa Janus

Molecules 2021, 26(6), 1714; https://doi.org/10.3390/molecules26061714 - 19 Mar 2021

Cited by 2 | Viewed by 2413

Abstract

Novel biocompatible compounds that stabilize proteins in solution are in demand for biomedical and/or biotechnological applications. Here, we evaluated the effect of six ionic liquids, containing mono- or dicholinium [Chol]_1or2 cation and anions of charged amino acids such as lysine [Lys], arginine [...] Read more.

Novel biocompatible compounds that stabilize proteins in solution are in demand for biomedical and/or biotechnological applications. Here, we evaluated the effect of six ionic liquids, containing mono- or dicholinium [Chol]_1or2 cation and anions of charged amino acids such as lysine [Lys], arginine [Arg], aspartic acid [Asp], or glutamic acid [Glu], on the structure, thermal, and storage stability of the Rapana thomasiana hemocyanin (RtH). RtH is a protein with huge biomedicinal potential due to its therapeutic, drug carrier, and adjuvant properties. Overall, the ionic liquids (ILs) induce changes in the secondary structure of RtH. However, the structure near the Cu-active site seems unaltered and the oxygen-binding capacity of the protein is preserved. The ILs showed weak antibacterial activity when tested against three Gram-negative and three Gram-positive bacterial strains. On the contrary, [Chol][Arg] and [Chol][Lys] exhibited high anti-biofilm activity against E. coli 25213 and S. aureus 29213 strains. In addition, the two ILs were able to protect RtH from chemical and microbiological degradation. Maintained or enhanced thermal stability of RtH was observed in the presence of all ILs tested, except for RtH-[Chol]₂[Glu]. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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19 pages, 4040 KiB

Open AccessArticle

Performance of p-Toluenesulfonic Acid–Based Deep Eutectic Solvent in Denitrogenation: Computational Screening and Experimental Validation

by Ainul F. Kamarudin, Hanee F. Hizaddin, Lahssen El-blidi, Emad Ali, Mohd A. Hashim and Mohamed K. Hadj-Kali

Molecules 2020, 25(21), 5093; https://doi.org/10.3390/molecules25215093 - 3 Nov 2020

Cited by 11 | Viewed by 3396

Abstract

Deep eutectic solvents (DESs) are green solvents developed as an alternative to conventional organic solvents and ionic liquids to extract nitrogen compounds from fuel oil. DESs based on p-toluenesulfonic acid (PTSA) are a new solvent class still under investigation for extraction/separation. This [...] Read more.

Deep eutectic solvents (DESs) are green solvents developed as an alternative to conventional organic solvents and ionic liquids to extract nitrogen compounds from fuel oil. DESs based on p-toluenesulfonic acid (PTSA) are a new solvent class still under investigation for extraction/separation. This study investigated a new DES formed from a combination of tetrabutylphosphonium bromide (TBPBr) and PTSA at a 1:1 molar ratio. Two sets of ternary liquid–liquid equilibrium experiments were performed with different feed concentrations of nitrogen compounds ranging up to 20 mol% in gasoline and diesel model fuel oils. More than 99% of quinoline was extracted from heptane and pentadecane using the DES, leaving the minutest amount of the contaminant. Selectivity was up to 11,000 for the heptane system and up to 24,000 for the pentadecane system at room temperature. The raffinate phase’s proton nuclear magnetic resonance (¹H-NMR) spectroscopy and GC analysis identified a significantly small amount of quinoline. The selectivity toward quinoline was significantly high at low solute concentrations. The root-mean-square deviation between experimental data and the non-random two-liquid (NRTL) model was 1.12% and 0.31% with heptane and pentadecane, respectively. The results showed that the TBPBr/PTSADES is considerably efficient in eliminating nitrogen compounds from fuel oil. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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21 pages, 1549 KiB

Open AccessReview

Applications of Ionic Liquids in Whole-Cell and Isolated Enzyme Biocatalysis

by Hasan Tanvir Imam, Vladimír Krasňan, Martin Rebroš and Andrew Craig Marr

Molecules 2021, 26(16), 4791; https://doi.org/10.3390/molecules26164791 - 7 Aug 2021

Cited by 34 | Viewed by 5682

Abstract

Ionic liquids have unique chemical properties that have fascinated scientists in many fields. The effects of adding ionic liquids to biocatalysts are many and varied. The uses of ionic liquids in biocatalysis include improved separations and phase behaviour, reduction in toxicity, and stabilization [...] Read more.

Ionic liquids have unique chemical properties that have fascinated scientists in many fields. The effects of adding ionic liquids to biocatalysts are many and varied. The uses of ionic liquids in biocatalysis include improved separations and phase behaviour, reduction in toxicity, and stabilization of protein structures. As the ionic liquid state of the art has progressed, concepts of what can be achieved in biocatalysis using ionic liquids have evolved and more beneficial effects have been discovered. In this review ionic liquids for whole-cell and isolated enzyme biocatalysis will be discussed with an emphasis on the latest developments, and a look to the future. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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76 pages, 30546 KiB

Open AccessReview

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

by Valerio Zullo, Anna Iuliano and Lorenzo Guazzelli

Molecules 2021, 26(7), 2052; https://doi.org/10.3390/molecules26072052 - 3 Apr 2021

Cited by 38 | Viewed by 6201

Abstract

Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid [...] Read more.

Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid and hydroxymethyl furfural, as well as solvents like cyrene or gamma-valerolactone. Therefore, there is great anticipation for novel applications involving materials and chemicals derived from sugars. In the field of ionic liquids (ILs), sugar-based ILs have been overlooked for a long time, mainly on account of their multistep demanding preparation. However, exploring new strategies for accessing sugar-based ILs, their study, and their exploitation, are attracting increasing interest. This is due to the growing concerns about the negative (eco)toxicity profile of most ILs in conjunction with their non-sustainable nature. In the present review, a literature survey concerning the development of sugar-based ILs since 2011 is presented. Their preparation strategies and thermal behavior analyses, sorted by sugar type, make up the first two sections with the intention to provide the reader with a useful guide. A final overview of the potential applications of sugar-based ILs and their future perspectives complement the present analysis. Full article

(This article belongs to the Special Issue Greener Ionic Liquids)

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