Multi-Interactions in Ionic Liquids for Natural Product Extraction

Zhang, Ying; Cao, Yingying; Wang, Hui

doi:10.3390/molecules26010098

Cited by 13 publications

(3 citation statements)

References 99 publications

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“…Even though a vast number of works on the structure and properties of ionic liquids are present in the literature, experimental as well as theoretical studies are needed on this topic, especially considering those ILs that are less often used and more environmentally benign, e.g., ammonium, diazolium/triazolium, or nature-inspired ILs [ 4 , 8 , 9 ]. Two of the most widely explored groups of ILs are imidazolium and pyridinium [ 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Markiewicz

Klimaszyk

Jarek

et al. 2021

IJMS

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The application of ionic liquids (ILs) has grown enormously, from their use as simple solvents, catalysts, media in separation science, or electrolytes to that as task-specific, tunable molecular machines with appropriate properties. A thorough understanding of these properties and structure–property relationships is needed to fully exploit their potential, open new directions in IL-based research and, finally, properly implement the appropriate applications. In this work, we investigated the structure–properties relationships of a series of alkyltriethylammonium bis(trifluoromethanesulfonyl)imide [TEA-R][TFSI] ionic liquids in relation to their thermal behavior, structure organization, and self-diffusion coefficients in the bulk state using DSC, FT-IR, SAXS, and NMR diffusometry techniques. The phase transition temperatures were determined, indicating alkyl chain dependency. Fourier-transformed infrared spectroscopy studies revealed the structuration of the ionic liquids along with alkyl chain elongation. SAXS experiments clearly demonstrated the existence of polar/non-polar domains. The alkyl chain length influenced the expansion of the non-polar domains, leading to the expansion between cation heads in polar regions of the structured IL. 1H NMR self-diffusion coefficients indicated that alkyl chain elongation generally caused the lowering of the self-diffusion coefficients. Moreover, we show that the diffusion of anions and cations of ILs is similar, even though they vary in their size.

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Section: Introductionmentioning

confidence: 99%

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Markiewicz

Klimaszyk

Jarek

et al. 2021

IJMS

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“…[1,2] Due to their low vapor pressure, they have become a sustainable alternative to the volatile organic solvents commonly used in a vast type of chemical processes, such as the extraction of valuable secondary metabolites from plants, which is well documented in the literature. [3][4][5][6] It has been claimed that the proven efficiency of ILs in the extractions of value-added compounds is enhanced due to their capacity to also solvate cellulose, which allows the goal compounds to be released in the media in larger quantities. In addition, if ultrasound radiation is used, simultaneously to ILs (ionic liquid-ultrasound assisted extraction, IL-USAE), the yield of the process increases even more.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, the long alkyl chain at the imidazolium ring seems to play an important role, because other 1-alkyl-3-imidazolium bromides (where alkyl chains were C 2 H 5 , C 6 H 13 , or C 10 H 21 ) had a poorer performance. This fact was attributed by the authors to the capacity of [Dodmim][Br] to form micelles and to its appropriate viscosity; nevertheless, other authors have reported that long alkyl groups at the cation promote an increase in the viscosity of ILs, [6,19] which could avoid a proper mass transfer of the analytes.…”

Section: Introductionmentioning

confidence: 99%

Phenolic compounds extraction from propolis using imidazole‐based ionic liquids: A theoretical and experimental study

Pale-Ezquivel

Vera‐Guzmán

Domínguez

et al. 2023

J of Physical Organic Chem

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The stability and non‐covalent interactions (NCI) of complexes formed by pinocembrin (PC), pinobanksin (PB), and pinobanksin 3‐acetate (PA) with a series of imidazolium‐based ionic liquids ([Bmim][BF4], [Bmim][Br], [Omim][Br], [Umim][Br], [OmimOH][Cl], and [UnmimOH][Br]) were evaluated through thermochemical parameters obtained from density functional theory (DFT) calculations, as well as atoms in molecules (AIM) and NCI analyses. The theoretical data were contrasted with experimental results obtained from the extraction of the three phenolic compounds from a propolis sample with aqueous solutions of the imidazolium salts. Calculations predicted that the complex formation processes at 298 K are spontaneous and close to the thermodynamic equilibrium (ΔGm ± 10 kcal/mol) in all the cases. However, [Omim][Br] forms the more stable complexes with the three flavonoids, which present a good correlation with greater amounts of PC, PB, and PA obtained during the extractions with this salt, with respect to the others. The hydrogen bond between the anion and the hydroxyl group of phenolic type is one of the most important NCI between the chemical species that conform the complexes; however, the functionalized cation UnmimOH+ can interact, even better than bromide, with the flavonoids through a hydrogen bond between hydroxyl groups. This could explain the higher values obtained through the Folin–Ciocalteu test used to evaluate the total phenolic content in the propolis extracts. This is not the case for the OmimOH+ functionalized cation, because the more electronegative counterion (Cl−) avoids an analogous behavior.

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Solid‐Phase Extraction and Clean‐Up Procedures in Pharmaceutical Analysis

Campíns‐Falcó

Herráez‐Hernández

Molíns-Legua

et al. 2022

Encyclopedia of Analytical Chemistry

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Solid‐phase extraction (SPE) using small cartridges filled with sorbents of a small particle size has rapidly established itself as an important sample clean‐up technique since the 1980s. It has prospered at the expense of traditional liquid–liquid extraction (LLE) which is considered labor‐intensive and frequently plagued by problems, such as emulsion formation and use of large volumes of hazardous solvents. A remarkable characteristic of SPE is its easy adaptation to on‐line mode by column switching techniques; switching can be affected manually or by automated controllers. The same analyte/sorbent interactions that are exploited in liquid chromatography (LC) are of use in SPE, but particle sizes employed are generally greater. Chemically bonded silica (SI), usually with C 18 and C 8 organic groups, is by far the most commonly used material. Cross‐linked polystyrene and other polymeric resins and mixed‐mode SPE sorbents are also widely used. Recently, different sorbents have been introduced in order to improve the selectivity such as molecularly imprinted polymers (MIPs) and immunoaffinity sorbents or to improve the extraction capacity through the increment of the surface‐to‐volume ratio (i.e. hypercross‐linked resins). Advances in material science in general and in nanomaterials in particular mark a trend in this field. Also, ionic liquids (ILs), carbon‐based materials, sol‐gel‐based compounds, and metal‐organic frameworks (MOFs), among others, are being introduced. Current trends in SPE are aimed toward the development of miniaturized systems which facilitate its automation and increase its precision, throughput, and cost‐effectiveness. Its compatibility with the goals of sustainable chemistry is remarkable. Examples of such trends are the new formats of SPE such as solid‐phase microextraction (SPME) including in‐tube solid‐phase microextraction (IT‐SPME) and tip‐based microextraction, between other formats. There are different approaches to automation for both off‐line and on‐line SPE, which involve different levels of apparatus cost. SPE is generally easier and cheaper than LLE for achieving this last goal. The precision obtained is similar for both techniques, while the recoveries obtained by SPE are generally better than those obtained by LLE. Enrichment, derivatization, and fractionation can also be carried out by use of SPE sorbents as supports.

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Multi-Interactions in Ionic Liquids for Natural Product Extraction

Cited by 13 publications

References 99 publications

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Phenolic compounds extraction from propolis using imidazole‐based ionic liquids: A theoretical and experimental study

Solid‐Phase Extraction and Clean‐Up Procedures in Pharmaceutical Analysis

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