Investigation of green solvents for the extraction of phenol and natural alkaloids: Solvent and extractant selection

Wu, Yue; Li, Wen; Vovers, Jessica; Lu, Hiep Thuan; Stevens, Geoffrey W.; Mumford, Kathryn A.

doi:10.1016/j.cej.2022.136054

Cited by 19 publications

(6 citation statements)

References 55 publications

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“…Fractional HSP values, which can be plotted on ternary diagrams to facilitate the assessment of interactions, have been used to identify green extraction solvents for alkaloids [32] and to screen solvent mixtures for pharmaceutical cocrystal formation [33]. HSP is a powerful tool used for solvent screening and is especially useful for large molecules, such as polymers or biomolecules, as highlighted by Abbott [34].…”

Section: Solubility Parametersmentioning

confidence: 99%

Solvent Replacement Strategies for Processing Pharmaceuticals and Bio-Related Compounds—A Review

Lee,

Chong,

Ota

et al. 2024

Liquids

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An overview of solvent replacement strategies shows that there is great progress in green chemistry for replacing hazardous di-polar aprotic solvents, such as N,N-dimethylformamide (DMF), 1-methyl-2-pyrrolidinone (NMP), and 1,4-dioxane (DI), used in processing active industrial ingredients (APIs). In synthetic chemistry, alcohols, carbonates, ethers, eucalyptol, glycols, furans, ketones, cycloalkanones, lactones, pyrrolidinone or solvent mixtures, 2-methyl tetrahydrofuran in methanol, HCl in cyclopentyl methyl ether, or trifluoroacetic acid in propylene carbonate or surfactant water (no organic solvents) are suggested replacement solvents. For the replacement of dichloromethane (DCM) used in chromatography, ethyl acetate ethanol or 2-propanol in heptanes, with or without acetic acid or ammonium hydroxide additives, are suggested, along with methanol acetic acid in ethyl acetate or methyl tert-butyl ether, ethyl acetate in ethanol in cyclohexane, CO2-ethyl acetate, CO2-methanol, CO2-acetone, and CO2-isopropanol. Supercritical CO2 (scCO2) can be used to replace many organic solvents used in processing materials from natural sources. Vegetable, drupe, legume, and seed oils used as co-extractants (mixed with substrate before extraction) can be used to replace the typical organic co-solvents (ethanol, acetone) used in scCO2 extraction. Mixed solvents consisting of a hydrogen bond donor (HBD) solvent and a hydrogen bond acceptor (HBA) are not addressed in GSK or CHEM21 solvent replacement guides. Published data for 100 water-soluble and water-insoluble APIs in mono-solvents show polarity ranges appropriate for the processing of APIs with mixed solvents. When water is used, possible HBA candidate solvents are acetone, acetic acid, acetonitrile, ethanol, methanol, 2-methyl tetrahydrofuran, 2,2,5,5-tetramethyloxolane, dimethylisosorbide, Cyrene, Cygnet 0.0, or diformylxylose. When alcohol is used, possible HBA candidates are cyclopentanone, esters, lactone, eucalytol, MeSesamol, or diformylxylose. HBA—HBA mixed solvents, such as Cyrene—Cygnet 0.0, could provide interesting new combinations. Solubility parameters, Reichardt polarity, Kamlet—Taft parameters, and linear solvation energy relationships provide practical ways for identifying mixed solvents applicable to API systems.

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Section: Solubility Parametersmentioning

confidence: 99%

Solvent Replacement Strategies for Processing Pharmaceuticals and Bio-Related Compounds—A Review

Lee,

Chong,

Ota

et al. 2024

Liquids

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“…They also compared the solvent-based affinity separation processes using Cyrene and sulfolane for aromatic/aliphatic separations [70]. Mumford et al found that Cyrene is not a suitable solvent for liquid-liquid extraction for natural alkaloid extraction [71]. As a novel biosolvent, Cyrene shows more than promising features useful for designing greener and more sustainable methods for crystallisation, purification, extraction and formulation of bioactive compounds from natural sources.…”

Section: Cyrene For Extraction and Separationmentioning

confidence: 99%

Preparation and Application of Green Sustainable Solvent Cyrene

Wang,

Dai,

Luo

et al. 2023

Chemistry

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The bio-based solvent dihydrolevoglucosenone (Cyrene) is a green and sustainable alternative to petroleum-based dipolar aprotic solvents. Cyrene can be prepared from cellulose in a simple two-step process and can be produced in a variety of yields. Cyrene is compatible with a large number of reactions in the chemical industry and can be applied in organic chemistry, biocatalysis, materials chemistry, graphene and lignin processing, etc. It is also green, non-mutagenic and non-toxic, which makes it very promising for applications. In this paper, we have also screened all articles related to Cyrene on the Web of Science and visualised them through Cite Space.

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“…1 Ionic liquids (ILs) were invented as an alternative green solvent with a few significant characteristics, including low vapor pressure at ambient temperature, good conductivity, high thermal stability, nonflammability, and nonvolatility. 2 These properties are due to the fact that ionic liquids have a melting point lower than the ambient temperature (100 °C) and are bulk ions that are asymmetrical (e.g., ammonium, imidazolium, etc.). 3 Such a melting temperature allows good separation for mixtures of high-temperature boiling components.…”

Section: Introductionmentioning

confidence: 99%

“…), with drawbacks that include low thermal stability, high volatility, low recyclability, high flammability, nonbiodegradability, toxicity, high costs, and low yield production, as well as many other environmental aspects . Ionic liquids (ILs) were invented as an alternative green solvent with a few significant characteristics, including low vapor pressure at ambient temperature, good conductivity, high thermal stability, nonflammability, and nonvolatility . These properties are due to the fact that ionic liquids have a melting point lower than the ambient temperature (100 °C) and are bulk ions that are asymmetrical (e.g., ammonium, imidazolium, etc.)…”

Section: Introductionmentioning

confidence: 99%

Separation Performance of Ethaline: Infinite Dilution Activity Coefficients and the Excess Thermodynamic Properties

Manyoni

Redhi

2023

J. Chem. Eng. Data

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This paper presents excess thermodynamic data of a mixture of choline chloride, a hydrogen bond acceptor (HBA), and ethylene glycol, a hydrogen bond donor (HBD), with a molar ratio of 1:2, correspondingly. This mixture is popularly known as ethaline. A gas−liquid chromatograph (GLC) fitted with a thermal conductivity detector (TCD) was used to determine infinite dilution activity coefficient (IDAC) values of different functional groups (e.g., alkanes, alkenes, alkynes, cycloalkanes, aromatics, alcohols, ketones, and water) for 32 different organic solutes at different temperatures (T = 313.15−343.15 K) and air pressures. The partial excess molar properties, including Gibbs free energy, enthalpy, and entropy, were computed from the infinite dilution activity coefficient measurements at T = 323.15 K. Furthermore, the separation performance of common separation problems, i.e., hexane/ benzene, cyclohexane/hexane, ethanol/toluene, and acetone/methanol, was evaluated through the selectivity and capacity values, and this was also computed from the infinite dilution activity coefficient values. It was found that ethaline could not be suitable for prospective separation issues, as a result of the poor thermodynamic data that were measured.

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Investigation of green solvents for the extraction of phenol and natural alkaloids: Solvent and extractant selection

Cited by 19 publications

References 55 publications

Solvent Replacement Strategies for Processing Pharmaceuticals and Bio-Related Compounds—A Review

Solvent Replacement Strategies for Processing Pharmaceuticals and Bio-Related Compounds—A Review

Preparation and Application of Green Sustainable Solvent Cyrene

Separation Performance of Ethaline: Infinite Dilution Activity Coefficients and the Excess Thermodynamic Properties

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