Kinetics and polarity effects in the synthesis of the ionic liquid, 1-hexyl-3-methyl-imidazolium bromide, using compressed CO2

Nwosu, Sylvia O.; Schleicher, Jay C.; Scurto, Aaron M.

doi:10.1016/j.supflu.2014.10.002

Cited by 4 publications

(2 citation statements)

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“…FTIR measurements were obtained at ambient pressure and 25 °C using a Mettler-Toledo ReactIR iC10 instrument with a SiComp IR probe that has been previously described by our research group. 21 IR characterization of the diethyl phosphate anion was obtained from the literature, and the anion PO stretching peak at 1240 cm −1 was analyzed for solvent dependent interactions with the IL anion. 22 IR spectra of pure [EMIm][DEP] and mixtures of the IL with cosolvent DMSO and antisolvent H 2 O were analyzed between 650 and 4000 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

Cellulose Solubility in Ionic Liquid Mixtures: Temperature, Cosolvent, and Antisolvent Effects

et al. 2016

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Select ionic liquids (ILs) dissolve significant quantities of cellulose through disruption and solvation of inter- and intramolecular hydrogen bonds. In this study, thermodynamic solid-liquid equilibrium was measured with microcrystalline cellulose in a model IL, 1-ethyl-3-methylimidazolium diethyl phosphate ([EMIm][DEP]) and mixtures with protic antisolvents and aprotic cosolvents between 40 and 120 °C. The solubility of cellulose in pure [EMIm][DEP] exhibits an asymptotic maximum of approximately 20 mass % above 100 °C. Solubility studies conducted on antisolvent mixtures with [EMIm][DEP] and [BMIm][Cl] indicate that protic solvents, ethanol, methanol, and water, significantly reduce the cellulose capacity of IL mixtures by 38-100% even at small antisolvent loadings (<5 mass %). Alternatively, IL-aprotic cosolvent (dimethyl sulfoxide, dimethylformamide, and 1,3-dimethyl-2-imidazolidinone) mixtures at mass ratios up to 1:1 enhance cellulose dissolution by 20-60% compared to pure [EMIm][DEP] at select temperatures. Interactions between the IL and molecular solvents were investigated by Kamlet-Taft solvatochromic analysis, FTIR, and NMR spectroscopy. The results indicate that preferential solvation of the IL cation and anion by co- and antisolvents impact the ability of IL ions to interact with cellulose thus affecting the cellulose dissolution capacity of IL-solvent mixtures.

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Section: Methodsmentioning

confidence: 99%

Cellulose Solubility in Ionic Liquid Mixtures: Temperature, Cosolvent, and Antisolvent Effects

et al. 2016

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“…Ionic liquids (ILs) with many attractive properties are considered potential substitutes to many traditional organic solvents in synthesis, catalysis, separation, , extraction, and other chemical processes, which recently attracted the attention of a growing number of researchers. − The high possibility for structure variations makes them potential “designer solvents”. − Their physicochemical properties can be tailored to suit a target function by changing the ion chemical structures or the incorporation of functional groups. − The solvent polarity is the most important property of ILs for choosing an IL for a specific industrial application. − For example, solubility of the proteins depends on the polarity of ILs …”

Section: Introductionmentioning

confidence: 99%

The Polarity of Ionic Liquids: Relationship between Relative Permittivity and Spectroscopic Parameters of Probe

Wang

Zhang

Yao

et al. 2019

Ind. Eng. Chem. Res.

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Polarity is one of the most important properties of ionic liquids (ILs) and an essential requirement when choosing an IL for a specific industrial application. Up to now, several empirical solvent polarity scales, such as Hildebrand solubility parameter, relative permittivity, the electronic transition energy of the longest-wavelength Vis absorption band of betaine dye no. 30 (E T (30) value) and the hyperfine coupling constant (A N ) etc. have been applied to ILs to provide quantitative evaluation of the polarity of ILs. Among them, the E T (30) value is widely used to reflect the polarity of ILs, however, it cannot be determined for opaque solvents or for solvents in which betaine dye no. 30 is insoluble. To broaden its scope of application and uniform the polarity standard, many approaches were used to predict the values of E T (30). Herein, we managed to apply a modified semiempirical reaction field of molecular solvents to predict the E T (30) and A N values of spin probe in ILs. Based on the experimental and estimated E T (30) values of 791 data entries, 240 ILs, 108 cations, and 34 anions of ILs, an "overall" polarity sequence of ILs can be obtained: primary, secondary, and tertiary alkylammonium salts > heterocyclic salts > quaternary alkylammonium salts ≈ phosphonium salts ≈ guanidinium salts.

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Liquid‐liquid‐phase Synthesis of exo‐Vinylene Carbonates from Primary Propargylic Alcohols: Catalyst Design and Recycling

Johnson¹,

Dabral²,

Peter

et al. 2020

ChemCatChem

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A straight‐forward approach to separate catalyst from the exo‐vinylene carbonate (EVC) products of the carboxylative cyclisation of primary propargylic alcohols has been developed. The liquid‐liquid phase synthesis utilises lipophilic silver(I) carboxylate salts and N,N‐dioctyl modified phosphine (FatPhos) ligands to enhance catalyst solubility in non‐polar solvents. Following simple liquid‐liquid phase separation, EVCs relevant as monomers for poly(urethane) and poly(carbonate) synthesis were isolated in the non‐miscible polar phase in good yields. In situ reaction monitoring by ReactIR gave insights into the reaction kinetics and informed the conditions used to afford good EVC selectivity. Under optimised conditions, silver leaching into the product phase was very minor as confirmed by ICP‐MS. Furthermore, a protocol for catalyst recycling by liquid‐liquid separation was demonstrated, with modest loss of catalytic activity over 3 runs.

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Kinetics and polarity effects in the synthesis of the ionic liquid, 1-hexyl-3-methyl-imidazolium bromide, using compressed CO2

Cited by 4 publications

References 60 publications

Cellulose Solubility in Ionic Liquid Mixtures: Temperature, Cosolvent, and Antisolvent Effects

Cellulose Solubility in Ionic Liquid Mixtures: Temperature, Cosolvent, and Antisolvent Effects

The Polarity of Ionic Liquids: Relationship between Relative Permittivity and Spectroscopic Parameters of Probe

Liquid‐liquid‐phase Synthesis of exo‐Vinylene Carbonates from Primary Propargylic Alcohols: Catalyst Design and Recycling

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