Low melting mixtures in organic synthesis – an alternative to ionic liquids?

Ruß, Carolin; König, Burkhard

doi:10.1039/c2gc36005e

Cited by 573 publications

(274 citation statements)

References 87 publications

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“…We wish to show the effect of this hydrogen-bond acceptor to the selectivity to furanic derivatives by preventing secondary reactions in the presence of different catalysts. One interesting class of solvents that was used in the conversion of carbohydrates to furanic derivatives is deep eutectic solvent (DES) [7] and low melting mixtures (LMMs) [8]. The concept of natural deep eutectic solvents was first introduced by Abbott et al in 2003 [9].…”

Section: Scheme 2 Examples Of Lmms and Dessmentioning

confidence: 99%

“…In general, DES is formed as a result of hydrogen-bonding interactions between two components. Therefore, one of the constituents is a hydrogen-bond acceptor (usually ChCl or NH4Cl), whereas the other constituent is a hydrogen-bond donor like natural polyols (glycerol), carboxylic acids (lactic acid (Lac), oxalic acid, citric acid) or ureas [7,8,[10][11][12][13][14][15][16][17]. If carbohydrates are used as hydrogen-bond donors with ChCl, the name used is "low melting mixtures" (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Jérôme

Vigier²

2017

Catalysts

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Abstract:The synthesis of furanic derivatives (5-hydroxymethylfurfural (HMF), furfural . . . ) from carbohydrates is of high interest for a wide range of applications. These reactions are carried out in the presence of various solvents, and among them choline chloride can be used. It is a salt that can form a low melting mixture with a carbohydrate (fructose, glucose . . . ) or a deep eutectic mixture with carboxylic acid. A review of the studies performed in the conversion of carbohydrates to furanic derivatives in the presence of choline chloride is presented here with the advantages and drawbacks of this solvent. Choline chloride can enhance the selectivity to HMF by stabilizing effect and allows the conversion of highly concentrated feed. However, the extraction of the products from these solvents still needs improvement.

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Section: Scheme 2 Examples Of Lmms and Dessmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Jérôme

Vigier²

2017

Catalysts

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“…Moreover, it was shown that addition of agents able to break the DES complex allows recrystallization and recovery of one or both of the initial components, since these remain in their molecular state upon melting [5,6]. DES exhibit a wide range of properties which make them an attractive family of solvents for different applications in catalysis, organic synthesis, dissolution and extraction processes, electrochemistry and material chemistry [2e5, 7,8]. The [Ch]Cl:urea mixture (1:2 mol), for example, was used in the Perkin condensation of cinnamic acid [9], reduction of epoxides [10] or in an electrophilic substitution of quinone derivatives [11].…”

Section: Introductionmentioning

confidence: 99%

Measurement and PC-SAFT modeling of solid-liquid equilibrium of deep eutectic solvents of quaternary ammonium chlorides and carboxylic acids

Pontes

Crespo

Martins

et al. 2017

Fluid Phase Equilibria

110

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a b s t r a c tIn this study the solid-liquid equilibria (SLE) of 15 binary mixtures composed of one of three different symmetrical quaternary ammonium chlorides and one of five different fatty acids were measured. The experimental data obtained showed extreme negative deviations to ideality causing large meltingtemperature depressions (up to 300 K) that are characteristic for deep eutectic systems. The experimental data revealed that cross-interactions between quaternary ammonium salt and fatty acid increase with increasing alkyl chain length of the quaternary ammonium chloride and with increasing chain length of the carboxylic acid. The pronounced decrease of melting temperatures in these deep eutectic systems is mainly caused by strong hydrogen-bonding interactions, and thermodynamic modeling required an approach that takes hydrogen bonding into account. Thus, the measured phase diagrams were modeled with perturbed-chain statistical associating fluid theory based on the classical molecular homonuclear approach. The model showed very good agreement with the experimental data using a semi-predictive modeling approach, in which binary interaction parameters between quaternary ammonium chloride and carboxylic acid correlated with chain length of the components. This supports the experimental findings on the phase behavior and interactions present in these systems and it allows estimating eutectic points of such highly non-ideal mixtures.

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“…It is composed of several components, which associate with each other in some way and result in a considerably lower freezing point of the mixture compared with each component [9,10]. Among the variety of DES, the mixture of quaternary ammonium salt and hydrogen bond donor is the most widely used type of DES in ionothermal synthesis of molecular sieves.…”

Section: Il and Desmentioning

confidence: 99%

Ionothermal Synthesis of Molecular Sieves

Tian

Liu

2016

Green Chemistry and Sustainable Technology

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The synthesis of molecular sieves in ionic liquid or deep eutectic solvent is termed ionothermal synthesis. It involves an ionic reaction environment with extremely low volatility, and thus, can avoid the safety risks of hydro/solvothermal reactions, and bring great convenience and flexibility to both the synthesis of molecular sieves and the study on their formation mechanisms. In this chapter, first introduced are the special physicochemical properties of ionic liquids and deep eutectic solvents, and the distinctive opportunities brought by them to synthesize molecular sieves. A detailed methodological illustration of ionothermal synthesis technique is provided subsequently. The molecular sieves ionothermally synthesized are summarized by their features such as composition, structure, porosity and morphology. Then follows a review on the fascinating structure-directing effect of various guest species in ionothermal synthesis. Finally, a prospect is given on the future development of ionothermal synthesis.

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Low melting mixtures in organic synthesis – an alternative to ionic liquids?

Cited by 573 publications

References 87 publications

Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Measurement and PC-SAFT modeling of solid-liquid equilibrium of deep eutectic solvents of quaternary ammonium chlorides and carboxylic acids

Ionothermal Synthesis of Molecular Sieves

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