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Journal ArticleDOI

Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis

07 Jul 1999-Chemical Reviews (American Chemical Society)-Vol. 99, Iss: 8, pp 2071-2084
About: This article is published in Chemical Reviews.The article was published on 1999-07-07. It has received 12178 citations till now. The article focuses on the topics: Ionic liquid & C4mim.
Citations
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Journal ArticleDOI
TL;DR: There are indications that switching from a normal organic solvent to an ionic liquid can lead to novel and unusual chemical reactivity, which opens up a wide field for future investigations into this new class of solvents in catalytic applications.
Abstract: Ionic liquids are salts that are liquid at low temperature (<100 degrees C) which represent a new class of solvents with nonmolecular, ionic character. Even though the first representative has been known since 1914, ionic liquids have only been investigated as solvents for transition metal catalysis in the past ten years. Publications to date show that replacing an organic solvent by an ionic liquid can lead to remarkable improvements in well-known processes. Ionic liquids form biphasic systems with many organic product mixtures. This gives rise to the possibility of a multiphase reaction procedure with easy isolation and recovery of homogeneous catalysts. In addition, ionic liquids have practically no vapor pressure which facilitates product separation by distillation. There are also indications that switching from a normal organic solvent to an ionic liquid can lead to novel and unusual chemical reactivity. This opens up a wide field for future investigations into this new class of solvents in catalytic applications.

5,387 citations

Journal ArticleDOI
TL;DR: There have been parallel and collaborative exchanges between academic research and industrial developments since the materials were first reported in 1914, it is demonstrated.
Abstract: In contrast to a recently expressed, and widely cited, view that “Ionic liquids are starting to leave academic labs and find their way into a wide variety of industrial applications”, we demonstrate in this critical review that there have been parallel and collaborative exchanges between academic research and industrial developments since the materials were first reported in 1914 (148 references)

4,865 citations

Journal ArticleDOI
TL;DR: Eutectic mixtures of urea and a range of quaternary ammonium salts are liquid at ambient temperatures and have interesting solvent properties.

3,550 citations

Journal ArticleDOI
TL;DR: A series of hydrophilic and hydrophobic 1-alkyl-3-methylimidazolium room temperature ionic liquids (RTILs) have been prepared and characterized to determine how water content, density, viscosity, surface tension, melting point, and thermal stability are affected by changes in alkyl chain length and anion.

3,469 citations

References
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Book
01 Jan 1966
TL;DR: Common physical techniques used in purification chemical methods used in Purification purification of organic chemicals Purification of inorganic and metal organic chemicals general methods for the purification classification of classes of compounds and natural products biochemicals and related products as mentioned in this paper.
Abstract: Common physical techniques used in purification chemical methods used in purification purification of organic chemicals purification of inorganic and metal organic chemicals general methods for the purification of classes of compounds purification of natural products biochemicals and related products.

10,132 citations

MonographDOI
12 Dec 2002
TL;DR: In this article, Solvent effects on acid/base equilibria and Tautomeric Equilibria have been investigated in terms of acid-base behavior and specific Solute/Solvent interactions.
Abstract: INTRODUCTION SOLUTE-SOLVENT INTERACTIONS Solutions Intermolecular Forces Solvation Preferential Solvation Micellar Solvation (Solubilization) Ionization and Dissociation CLASSIFICATION OF SOLVENTS Classification of Solvents According to Chemical Constitution Classification of Solvents Using Physical Constants Classification of Solvents in Terms of Acid-Base Behaviour Classification of Solvents in Terms of Specific Solute/Solvent Interactions Classification of Solvents Using Multivariate Statistical Methods SOLVENT EFFECTS ON THE POSITION OF HOMOGENEOUS CHEMICAL EQUILIBRIA General Remarks Solvent Effects on Acid/Base Equilibria Solvent Effects on Tautomeric Equilibria Solvent Effects on other Equilibria SOLVENT EFFECTS ON THE RATES OF HOMOGENEOUS CHEMICAL REACTIONS General Remarks Gas-Phase Reactivities Qualitative Theory of Solvent Effects on Reaction Rates Quantitative Theories of Solvent Effects on Reaction Rates Specific Solvation Effects on Reaction Rates SOLVENT EFFECTS ON THE ABSORPTION SPECTRA OF ORGANIC COMPOUNDS General Remarks Solvent Effects on UV/Vis Spectra Solvent Effects on Infrared Spectra Solvent Effects on Electron Spin Resonance Spectra Solvent Effects on Nuclear Magnetic Resonance Spectra EMPIRICAL PARAMETERS OF SOLVENT POLARITY Linear Gibbs Energy Relationships Empirical Parameters of Solvent Polarity from Equilibrium Measurements Empirical Parameters of Solvent Polarity from Kinetic Measurements Empirical Parameters of Solvent Polarity from Spectroscopic Measurements Empirical Parameters of Solvent Polarity from Other Measurements Interrelation and Application of Solvent Polarity Parameters Multiparameter Approaches SOLVENTS AND GREEN CHEMISTRY Green Chemistry Reduction of Solvent Use Green Solvent Selection Non-Traditional Solvents Outlook APPENDIX: PROPERTIES, PURIFICATION, AND USE OF ORGANIC SOLVENTS Physical Properties Purification of Organic Solvents Spectroscopic Solvents Solvents as Reaction Media Solvents for Recrystallization Solvents for Extraction and Partitioning (Distribution) Solvents for Adsorption Chromatography Solvents for Acid/Base Titrations in Non-Aqueous Media Solvents for Electrochemistry Toxicity of Organic Solvents

5,515 citations

Journal ArticleDOI
TL;DR: There are indications that switching from a normal organic solvent to an ionic liquid can lead to novel and unusual chemical reactivity, which opens up a wide field for future investigations into this new class of solvents in catalytic applications.
Abstract: Ionic liquids are salts that are liquid at low temperature (<100 degrees C) which represent a new class of solvents with nonmolecular, ionic character. Even though the first representative has been known since 1914, ionic liquids have only been investigated as solvents for transition metal catalysis in the past ten years. Publications to date show that replacing an organic solvent by an ionic liquid can lead to remarkable improvements in well-known processes. Ionic liquids form biphasic systems with many organic product mixtures. This gives rise to the possibility of a multiphase reaction procedure with easy isolation and recovery of homogeneous catalysts. In addition, ionic liquids have practically no vapor pressure which facilitates product separation by distillation. There are also indications that switching from a normal organic solvent to an ionic liquid can lead to novel and unusual chemical reactivity. This opens up a wide field for future investigations into this new class of solvents in catalytic applications.

5,387 citations

Journal ArticleDOI
TL;DR: New, hydrophobic ionic liquids with low melting points (<−30 °C to ambient temperature) have been synthesized and investigated, based on 1,3-dialkyl imidazolium cations and hydrophilic anions and thus water-soluble.
Abstract: New, hydrophobic ionic liquids with low melting points (<−30 °C to ambient temperature) have been synthesized and investigated, based on 1,3-dialkyl imidazolium cations and hydrophobic anions. Other imidazolium molten salts with hydrophilic anions and thus water-soluble are also described. The molten salts were characterized by NMR and elemental analysis. Their density, melting point, viscosity, conductivity, refractive index, electrochemical window, thermal stability, and miscibility with water and organic solvents were determined. The influence of the alkyl substituents in 1, 2, 3, and 4(5)-positions on these properties was scrutinized. Viscosities as low as 35 cP (for 1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide (bis(triflyl)amide) and trifluoroacetate) and conductivities as high as 9.6 mS/cm were obtained. Photophysical probe studies were carried out to establish more precisely the solvent properties of 1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide). The hydrophobi...

4,089 citations

Journal ArticleDOI
TL;DR: In this paper, a new approach for the calculation of solvation phenomena is presented, based on the perfect, Le., conductor-like, screening of the solute molecule and a quantitative calculation of the deviations from ideality appearing in real solvents.
Abstract: Starting from the question of why dielectric continuum models give a fairly good description of molecules in water and some other solvents, a totally new approach for the calculation of solvation phenomena is presented. It is based on the perfect, Le., conductor-like, screening of the solute molecule and a quantitative calculation of the deviations from ideality appearing in real solvents. Thus, a new point of view to solvation phenomena is presented, which provides an alternative access to many questions of scientific and technical importance. The whole theory is based on the results of molecular orbital continuum solvation models. A few representative solvents are considered, and the use of the theory is demonstrated by the calculation of vapor pressures, surface tensions, and octanol/water partition coefficients.

3,220 citations