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At least 19 recordsLinked to original sources
PubMed2002

Enzyme catalysis in ionic liquids.

Ionic liquids offer new possibilities for the application of solvent engineering to biocatalytic reactions. Although in many cases ionic liquids have simply been used to replace organic solvents, they have often led to improved process performance. Unlike conventional organic solvents, ionic liquids possess no vapor pressure, are able to dissolve many compounds, and can be used to form two-phase systems with many solvents. To date, reactions involving lipases have benefited most from the use of ionic liquids, but the use of ionic liquids with other enzymes and in whole-cell processes has also been described. In some cases, remarkable results with respect to yield, (enantio)selectivity or enzyme stability were observed.

Bacteria↗
PubMed2001

Capillary electrophoretic application of 1-alkyl-3-methylimidazolium-based ionic liquids.

Ionic substances with melting points at or close to room temperature are referred to as ionic liquids. Interest in ionic liquids for their potential in different chemical processes is increasing, because they are environmentally benign and are good solvents for a wide range of both organic and inorganic materials. In this study, a capillary electrophoretic method for resolving phenolic compounds found in grape seed extracts is reported. The method, in which 1-alkyl-3-methylimidazolium-based ionic liquids are used as the running electrolytes, is simple and reproducible. The separation mechanism seems to involve association between the imidazolium cations and the polyphenols. The role of the alkyl substituents on the imidazolium cations was investigated and will be discussed.

Journal Article↗
PubMed2004

Electrospray mass spectrometry of undiluted ionic liquids.

Ionic liquids have been analyzed in undiluted form using electrospray mass spectrometry (ES-MS); results indicate that signal-to-noise ratios for minor constituents are comparable to those observed in conventional, diluted ES-MS and that this approach could be readily applied for mass spectrometric analysis of ionic liquids and ionic impurities/additives dissolved therein, especially those that are solvent reactive.

Journal Article↗
PubMed2006

Lewis base ionic liquids.

Ionic liquids which are (weak) Lewis bases have a number of interesting and useful properties different to those of traditional ionic liquids, including volatility and the possibility of being distillable in some cases, a base catalysis effect in others and enhancement of the acidity of dissolved acids.

Journal Article↗
PubMed2006

Reversible physical absorption of SO2 by ionic liquids.

Ionic liquids can reversibly absorb large amounts of molecular SO(2) gas under ambient conditions with the gas captured in a restricted configuration, possibly allowing SO(2) to probe the internal cavity structures in ionic liquids besides being useful for SO(2) removal in pollution control.

Journal Article↗
PubMed2005

Transprotection of silyl ethers of nucleosides in FeCl3 based ionic liquids.

Ionic liquid mediated deprotection of tert-butyldimethyl silyl (TBDMS) ethers derived from various primary and secondary alcohols have been studied and the reaction conditions optimized. Deprotection of the silyl ethers in FeCl3 based ionic liquids in presence of acetic anhydride yielded the acetate esters of the corresponding alcohols in good yields. The transprotection methodology was extended to the silyl ethers of nucleosides to yield the corresponding acetylated products.

Acetates↗
PubMed2004

Using Caenorhabditis elegans to probe toxicity of 1-alkyl-3-methylimidazolium chloride based ionic liquids.

Ionic liquids are gaining attention as new solvents within the green chemistry community; however this attention has quickly outstripped current environmental and toxicological data available. In the present communication, we establish the use of Caenorhabditis elegans as a model organism for inexpensively and quickly exploring toxicological effects of 1-alkyl-3-methylimidazolium chloride ionic liquids.

Animals↗
PubMed2006

Amineborane-based chemical hydrogen storage: enhanced ammonia borane dehydrogenation in ionic liquids.

Ionic liquids are shown to provide advantageous media for amineborane-based chemical hydrogen storage systems. Both the extent and rate of hydrogen release from ammonia borane dehydrogenation are significantly increased at 85, 90, and 95 degrees C when the reactions are carried out in 1-butyl-3-methylimidazolium chloride compared to analogous solid-state reactions. NMR studies in conjunction with DFT/GIAO chemical shift calculations indicate that both polyaminoborane and the diammoniate of diborane, [(NH3)2BH2+]BH4-, are initial products in the reactions.

Journal Article↗
PubMed2006

Chemoenzymatic dynamic kinetic resolution of rac-1-phenylethanol in ionic liquids and ionic liquids/supercritical carbon dioxide systems.

Continuous dynamic kinetic resolution processes in different ionic liquid/supercritical carbon dioxide biphasic systems were carried out by simultaneously using both immobilized Candida antarctica lipase B (Novozym 435) and silica modified with benzenosulfonic acid (SCX) catalysts at 40 degrees C and 10 MPa. SCX was seen to act as an efficient heterogeneous chemical catalyst for the racemization of (S)-1-phenylethanol in different ionic liquid media ([emim][NTf(2)], [btma][NTf(2)] and [bmim][PF(6)]). Coating both chemical and enzymatic catalysts with ILs greatly improved the efficiency of the process, providing a good yield (76%) of (R)-1-phenylethyl propionate product with excellent enantioselectivity (ee = 91-98%) in continuous operation.

Benzyl Alcohols↗
PubMed2004

Matrix-assisted laser desorption/ionization mass spectrometry for the characterization of ionic liquids and the analysis of amino acids, peptides and proteins in ionic liquids.

Ionic liquids are interesting solvents for a number of applications in chemistry and biotechnology. We characterized five different ionic liquids by laser desorption/ionization (LDI) and by matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS) and studied the analysis of amino acids, peptides and proteins dissolved in these solvents. Signals of both anions and cations of the ionic liquids could be observed both in LDI- and in MALDI-MS. In the latter case, adduct formation between anions and cations of the analytes was observed. Amino acids, peptides and proteins could be analyzed in ionic liquids after addition of matrix substances. Sodium and potassium adducts were not observed in any analysis involving ionic liquids. Low molecular mass compounds and peptides could be analyzed best in the presence of water-immiscible ionic liquids, whereas proteins gave the best results in water-miscible ionic liquids. Optimal analysis conditions such as molar matrix-to-analyte and ionic liquid-to-matrix ratios were determined. Homogeneity of samples in the presence of ionic liquids was reduced compared with classical MALDI preparations. Relative quantitation of amino acids was possible using isotope-labeled internal standards. MALDI-MS thus can be used for the analysis of chemical reactions and the screening of enzyme-catalyzed reactions in ionic liquids and for the analysis of the biocatalysts dissolved in these solvents. Theoretical aspects of ion formation in the presence of ionic liquids both in LDI and MALDI analysis are discussed.

Amino Acids↗
PubMed2003

Catalytic asymmetric hydrogenation in a room temperature ionic liquid using chiral Rh-complex of ionic liquid grafted 1,4-bisphosphine ligand.

Introduction of imidazolium ionic liquid pattern to the catalyst not only avoided catalyst leaching but also increased the stability of catalyst in ionic liquid, and thus, the Rh-complex of 1,4-bisphosphine bearing two imidazolium salt moieties was successfully immobilized in an ionic liquid and reused several times for the hydrogenation of an enamide without significant loss of catalytic efficiency.

Journal Article↗
PubMed2006

Assessing the roles of the constituents of ionic liquids in dynamic solvation: Comparison of an ionic liquid in micellar and bulk form.

Dynamic solvation of the dye, coumarin 153, is compared in an ionic liquid that forms micelles in water against the bulk solvent. This provides the unprecedented opportunity of investigating the behavior of the ionic liquid in two globally different configurations. It is proposed that the imidazolium moiety is in both cases responsible for the majority of the solvation, which manifests itself in the first 100 ps. Exploiting the use of ionic liquids capable of accommodating specific structures thus provides a deeper insight into how solutes interact with these fascinating and interesting solvents (at least those that are imidazolium based) that are gaining ever increasing interest in the scientific community.

Coumarins↗
PubMed2007

Michael additions of methylene active compounds to chalcone in ionic liquids without any catalyst: the peculiar properties of ionic liquids.

Michael additions of malonodinitrile as well as several other reagents to chalcone have been found to proceed well in pure ionic liquids, without the addition of any catalyst. The catalytic effect of the residual acidity caused by hydrolysis of ionic liquids anions was excluded because HCl in dichloromethane did not catalyse the Michael addition of malonodinitrile. Piperidine was tested as the catalyst and was found to be a much better catalyst in ionic liquids than in dichloromethane. Therefore, the following question arose: what is the effect of ionic liquids on the dissociation constants of C--H acids?

Journal Article↗
PubMed2005

Magnitude and directionality of interaction in ion pairs of ionic liquids: relationship with ionic conductivity.

The intermolecular interaction energies of nine ion pairs of room temperature ionic liquids were studied by MP2/6-311G level ab initio calculations. The magnitude of the interaction energies of 1-ethyl-3-methylimidazolium (emim) complexes follows the trend CF(3)CO(2)(-) > BF(4)(-) > CF(3)SO(3)(-) > (CF(3)SO(2))(2)N(-) approximately PF(6)(-) (-89.8, -85.2, -82.6, -78.8, and -78.4 kcal/mol, respectively). The interaction energies of BF(4)(-) complexes with emim, ethylpyridinium (epy), N-ethyl-N,N,N-trimethylammonium ((C(2)H(5))(CH(3))(3)N), and N-ethyl-N-methylpyrrolidinium (empro) are not very different (-85.2, -82.8, -84.6, and -84.4 kcal/mol, respectively), while the size of the orientation dependence of the interaction energies follows the trend emim > epy approximately (C(2)H(5))(CH(3))(3)N > empro. Comparison with the experimental ionic conductivities shows that the magnitude and directionality of the interaction energy of the ion pairs play a crucial role in determining the ionic dissociation/association dynamics in the ionic liquids. The electrostatic interaction is the major source of attraction between ions. The induction contribution is small but not negligible. The hydrogen bonding with the C(2)-H of imidazolium is not essential for the attraction in the ion pair. The interaction energy of the BF(4)(-) complex with 1-ethyl-2,3-dimethylimidazolium (em2im) (-81.8 kcal/mol) is only 4% smaller than that of the emim complex.

Journal Article↗
PubMed2006

Combustible ionic liquids by design: is laboratory safety another ionic liquid myth?

The non-flammability of ionic liquids (ILs) is often highlighted as a safety advantage of ILs over volatile organic compounds (VOCs), but the fact that many ILs are not flammable themselves does not mean that they are safe to use near fire and/or heat sources; a large group of ILs (including commercially available ILs) are combustible due to the nature of their positive heats of formation, oxygen content, and decomposition products.

Journal Article↗
PubMed2006

Penicillin acylase catalysis in the presence of ionic liquids.

Several ionic liquids were used as reaction media for penicillin G acylase catalysis. In all the assayed ionic liquids, [bmim]PF6 proved good media for PGA-catalyzed hydrolysis. A novel [bmim]PF6/water two-phase system is provided for 6-aminopenicillanic acid (APA) production, which will be more benefical than aquous batch systems used widely in industrial production of APA.

Catalysis↗
PubMed2004

Nucleophilicity in ionic liquids. 3. Anion effects on halide nucleophilicity in a series of 1-butyl-3-methylimidazolium ionic liquids.

We have continued the study of halide nucleophilicity in ionic liquids, concentrating on the effect of changing the anion ([BF(4)](-), [PF(6)](-), [SbF(6)](-), [OTf](-), and [N(Tf)(2)](-)) when the cation is [bmim](+) (where bmim = 1-butyl-3-methylimidazolium). It was found that the nucleophilicities of all the halides were lower in all of the ionic liquids than in dichloromethane. Changing the anion affected the order of halide nucleophilicity, e.g., in [bmim][BF(4)] the order of nucleophilicity was Cl(-)>Br(-)>I(-) while in [bmim][N(Tf)(2)] the order was Cl(-)<Br(-)<I(-). It was also found that the nucleophilicity of each halide was different in each ionic liquid, with chloride being almost four times as nucleophilic in [bmim][BF(4)] as in [bmim][SbF(6)]. Similarly bromide was more than four times as nucleophilic in [bmim][BF(4)] as in [bmim][PF(6)]. The activation parameters DeltaG++, DeltaH++, and DeltaS++ have been measured for the reaction of chloride in each of the ionic liquids, plus the reaction of bromide in [bmim][BF(4)] and [bmim][PF(6)]. These data were also compared to each other as well as to a similar reaction in dichloromethane (where these parameters have been estimated for both the free ion and the ion-pair). These studies show that the reaction in the ionic liquids has a high activation free energy barrier, due to the solvent-solute interactions within the ionic liquids. These interactions are described and discussed.

Journal Article↗