Relevant bibliographies by topics / Chiral ionic liquids

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Chiral ionic liquids'

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Published: 4 June 2021
Last updated: 15 February 2022

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Journal articles on the topic "Chiral ionic liquids"

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Nobuoka, Kaoru, Satoshi Kitaoka, Tsutomu Kojima, Yuuki Kawano, Kazuya Hirano, Masakazu Tange, Shunsuke Obata, Yuki Yamamoto, Thomas Harran, and Yuich Ishikawa. "Proline Based Chiral Ionic Liquids for Enantioselective Michael Reaction." Organic Chemistry International 2014 (November 20, 2014): 1–9. http://dx.doi.org/10.1155/2014/836126.

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Chiral ionic liquids, starting from (S)-proline, have been prepared and evaluated the ability of a chiral catalyst. In Michael reaction of trans-β-nitrostyrene and cyclohexanone, all the reactions were carried out under homogeneous conditions without any solvent except for excess cyclohexanone. The chiral ionic liquid catalyst with the positive charge delocalized bulky pyrrolidinium cation shows excellent yields (up to 92%), diastereoselectivities (syn/anti = 96/4), and enantioselectivities (up to 95% ee) and could be reused at least three times without any loss of its catalytic activity. Such results demonstrated a promising new approach for green and economic chiral synthesis by using the chiral ionic liquids as a chiral catalyst and a chiral medium.
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Flieger, Jolanta, Joanna Feder-Kubis, and Małgorzata Tatarczak-Michalewska. "Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques." International Journal of Molecular Sciences 21, no. 12 (June 15, 2020): 4253. http://dx.doi.org/10.3390/ijms21124253.

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Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.
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Vasiloiu, Maria, Sonja Leder, Peter Gaertner, Kurt Mereiter, and Katharina Bica. "Coordinating chiral ionic liquids." Organic & Biomolecular Chemistry 11, no. 46 (2013): 8092. http://dx.doi.org/10.1039/c3ob41635f.

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Lauth-de Viguerie, Nancy, Cosmin Patrascu, Claudia Sugisaki, Christophe Mingotaud, Jean-Daniel Marty, and Yves Génisson. "New Pyridinium Chiral Ionic Liquids." HETEROCYCLES 63, no. 9 (2004): 2033. http://dx.doi.org/10.3987/com-04-10133.

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Zalewska, Karolina, and Luis C. Branco. "Organocatalysis with Chiral Ionic Liquids." Mini-Reviews in Organic Chemistry 11, no. 2 (June 2014): 141–53. http://dx.doi.org/10.2174/1570193x1102140609120011.

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Bica, Katharina, and Peter Gaertner. "Applications of Chiral Ionic Liquids." European Journal of Organic Chemistry 2008, no. 19 (July 2008): 3235–50. http://dx.doi.org/10.1002/ejoc.200701107.

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Ahn, Sangbum, Shohei Yamakawa, and Kazuo Akagi. "Liquid crystallinity-embodied imidazolium-based ionic liquids and their chiral mesophases induced by axially chiral tetra-substituted binaphthyl derivatives." Journal of Materials Chemistry C 3, no. 16 (2015): 3960–70. http://dx.doi.org/10.1039/c4tc02968b.

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The novel liquid crystalline ionic liquids (LCILs) were synthesised by introducing LC chains into both sides of imidazolium derivatives. The LCILs exhibited chiral nematic (N*) phases when the chiral dopants were added to the LCILs.
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Singh, Avtar, Nirmaljeet Kaur, and Harish Kumar Chopra. "Enantioselective Reduction Reactions Using Chiral Ionic Liquids: An Overview." Current Organic Synthesis 15, no. 5 (July 5, 2018): 578–86. http://dx.doi.org/10.2174/1570179415666180427111428.

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Background: Enantioselective reduction reactions play a key role to synthesize compounds of industrial importance. A number of metal and biocatalysts have been developed for their use in this reaction. Chiral ionic liquids (CILs) have been widely used as the reaction medium and the organocatalysts in enantioselective reduction reactions. Objective: This paper focuses on the systematic literature review about the use of chiral ionic liquids (CILs) in the enantioselective reduction reaction. The mechanistic aspects of these species are also taken into account. Conclusion: This review concludes that a number of chiral ionic liquids (CILs) have been successfully employed as the organocatalysts and the reaction medium in the enantioselective reduction reactions. The review also gives an insight into the role of these species in the reaction mechanism. For most of the reactions, chiral ionic liquids provide promising results in terms of yield and enantioselectivity. The recyclability of these chiral moieties from the reaction mixtures offers an additional benefit for the use of these species in asymmetric reactions.
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Wang, Hong Li, Xiao Ling Hu, Ping Guan, Jin Yang Yu, and Yi Mei Tang. "Synthesis and Characterization of Novel Ester Functionalized Chiral Ionic Liquids." Advanced Materials Research 197-198 (February 2011): 471–77. http://dx.doi.org/10.4028/www.scientific.net/amr.197-198.471.

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Three different chiral ionic liquids, chloride (R)-(+)-β-(1-methyl-imidazole)–propio-nate, (R)-(+)-β-(1-methyl-imidazole)-propionate terafluoroborate and hexafluorophosphate, weresuccessfully synthesized via the nucleophilic substitution reaction and the anion metathesis reaction, with (S)-(-)-2-chloro-propionic acid as the chiral source. Structures of the chiral io-nic liquids have been characterized by the infrared spectroscopy, nuclear magnetic resonancespectroscopy and quantum chemical structure optimization method. These new ionic materia-ls can be used as building blocks for the synthesis of ionic liquids.
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Marwani, Hadi. "Spectroscopic evaluation of chiral and achiral fluorescent ionic liquids." Open Chemistry 8, no. 4 (August 1, 2010): 946–52. http://dx.doi.org/10.2478/s11532-010-0062-7.

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AbstractIn this study, spectroscopic investigation of chiral and achiral room temperature ionic liquids is achieved. New ionic liquids were prepared via metathesis, accomplished by the reaction of either L-phenylalanine ethyl ester hydrochloride, chlorpromazine hydrochloride or 1,10-Phenanthroline monohydrate hydrochloride with lithium bis(trifluoromethane) sulfonamide in water. The resulting ionic liquids were produced in high yield and purity. The results obtained by use of 1H NMR and IR experiments were in very good agreement with the chemical structures of the synthesized ionic liquids. In addition, the results of thermal gravimetric analysis suggested that these ionic liquids have good thermal stability. UV-Vis and fluorescence spectroscopy measurements indicated that these ionic liquids are strongly optically absorbent and fluorescent. Lastly, time-based fluorescence steady-state measurements demonstrated the high photostability of these ionic liquids.
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Dissertations / Theses on the topic "Chiral ionic liquids"

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Foreiter, M. B. "Novel chiral ionic liquids." Thesis, Queen's University Belfast, 2014. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.675450.

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Chiral ionic liquids have been present in the literature for more than a decade. The development of original chiral systems of ions is currently far more difficult than ever before. The path of innovation in this topic, however, should not be focussed exclusively on the introduction of chirality into the ionic liquid structure, but should go beyond, towards further functionalisation of these species. The combination of chirality and a functional moiety has been the starting point for the present work. Here, a focus was on creation of chiral ionic liquids possessing distinct functional groups: a strong hydrogen-bonding thiourea group was selected. Consequently, a series of novel chiral thiouronium salts were synthesised. The chirality was sourced in cheap, but structurally robust, chiral amines: (S)-1- phenylethylamine and (+)-dehydroabietylamine. Because the thiourea moiety can be functionalised at five different sites, a wide range of thiouronium and thiourea-functionalised ionic liquids could be prepared and analysed, and the influence coming from their structural diversity explored. The crucial point for the project was a confirmation of rotameric behaviour in these new thiouronium systems. Here, the hindered rotation has been examined by NMR spectroscopy, and compared with literature findings. The key message concludes that, in the thiouronium system, the C-S rotation predominates when placed in a highly polar solvent; then the syn syn conformation dominates. When, on the other hand, the constraints of the surroundings are eliminated, the syn-anti form is energetically preferable. Here, the rotamerism of the thiouronium cation in a neat liquid form was examined for the first time. Finally, these novel chiral compounds have found applications based on molecular recognition by the thiourea moiety. The discrimination of chiral oxoanions by these salts using NMR spectroscopy has been successful. A strong, double hydrogen-bonded connection between the chiral thiouronium moiety and the oxoanion proved to be a key point, generating results a competitive with the literature results. Following this approach, the separation capabilities of thiouronium systems were also explored, given that they can be effective agents for oxoanion extractions. This work demonstrated that a careful design of functional molecules is scientifically significant, and can have a great impact on their applications.
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McCarron, Philip. "Chiral separations using chiral amino acid ionic liquids." Thesis, Queen's University Belfast, 2016. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.707833.

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The backbone of this work is to make a chiral ionic liquid with enantioselective properties. It is envisaged that the ionic liquid will be a component part of a gel matrix, or membrane, which holds a racemic drug in solution, and shows preferential affinity to one enantiomer. This would allow favoured diffusion of the unattached enantiomer, and such a system would be ideal as the reservoir in a drug delivery system. To test this idea, chiral amino acid ionic liquids were used. The thesis introduces ionic liquids by definition, classification, properties and industrial applications, and also the anti-inflammatory drug ibuprofen as the model test compound. The main application, discussed in Chapter 2, was the separation of ibuprofen enantiomers using chiral amino acid ionic liquids as the chiral selector with liquid-liquid extractions. Ionic liquid preparation is included in Chapter 3, as is an overview of HPLC analysis. Chiral interactions may depend on many factors, and these are explained in Chapter 4. Interaction experiments were performed, and techniques complementary to HPLC also explored. Chapter 5 highlights the subtle nature of enantiomeric separations. Here, an increase in enantiomeric excess percentage by physical processes was demonstrated using ionic liquid test strips. They were developed to help determine enantiomeric excess of ibuprofen as it passed through a series of ionic liquid impregnated sections on paper or silica. In Chapter 6, the analytical and preparative technique of countercurrent chromatography is discussed. It concludes with an application that used a thiouronium based ionic liquid to resolve racemic mandelic acid. Overall, the aim was not to develop and optimise a specific application, but to demonstrate proof-of-principle for using chiral ionic liquids to achieve enantiomeric separation. Two new methodologies were unambiguously demonstrated: the use of paper strips and countercurrent chromatography, and both appear to be worthy of future development.
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DONALD, GREGORY THOMAS. "Model Chiral Ionic Liquids for High Performance Liquid Chromatography Stationary Phases." University of Cincinnati / OhioLINK, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1214325450.

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Yunis, Ruhamah. "Synthesis and characterization of amino acid ionic liquids and low symmetry ionic liquids based on the triaminocyclopropenium cation." Thesis, University of Canterbury. Chemistry, 2015. http://hdl.handle.net/10092/10207.

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This thesis involves the synthesis of two main classes of triaminocyclopropenium (tac) Ionic Liquids (ILs) (i) Amino Acid Ionic Liquids (AAILs) and (ii) reduced-symmetry cations. [C₃(NEt₂)₂(NRR’)]X (X = TFSA and MeSO₄) were prepared, whereby NHR is derived from amino acids. Optically pure AAILs, [E₄AminoAcid]X (X = TFSA and MeSO₄) were obtained as a mixture of the IL and its zwitterion. The ratios of these mixtures were determined by pH titration and microanalysis. The AAILs specific rotations and pKa values were determined. AAILs can be used for chiral discrimination and form diasterreomeric salts with the entioenriched sodium salt of Mosher’s acid. The AAILs were also successfully used as a solvent and/or catalyst in an aldol reaction and a Diels-Alder reaction. The low-molecular weight series, [C₃(NMe₂)₂(NRR’)]X and [C₃(NMe₂)₂(NR’2)]X was synthesized and characterized: protic ILs NRR’, where R = ethyl, propyl, allyl, butyl, - CH2CH2OCH₃ and pentyl, R’ = H and X = TFSA: and aprotic ILs NRR’, where R = Me, R’ = ethyl, allyl, propyl, butyl, -CH2CH2OCH₃ and hexyl and X = TFSA and DCA. ILs with C2v symmetry [C₃(NEt₂)₂(NH2)]X (X = TFSA and MeSO₄), [C₃(NEt₂)₂(NBu2)]I, [C₃(NEt₂)₂(NHex₂)]I and [C₃(NEt₂)₂(NHex₂)]OTf were also synthesized and characterized. The C₃h cations, [C₃(NMeR)₃]X (R = ethyl, allyl, -CH2CH2OCH₃ and phenyl, X = TFSA and DCA) were successfully prepared as well. The D₃h cation salts [C₃(NEt₂)₃]X (X = MeC6H4SO₃, OTf, I and F5C6O) and [C₃(NBu2)₃]X (X = B(CN)4 and FAP) were also prepared. The tac-based ILs [C₃(NEt₂)₃]+ and [C₃(NBu2)₃]+ were also complexed with metal halides - - 2- 2- forming salts with FeCl₄ , SnCl₃ , CuCl₄ and ZnCl₄ . Reaction of pentachlorocyclopropane (C₃Cl5H) with BuNH2 gave the open ring allylium product [H2C₃(NBuH)4]2+. This was characterized as Cl- and TFSA- salt. During the synthesis of [C₃(NMe₂)₃]Cl, the open ring cation [HC₃(NMe₂)4]+ was also isolated and was characterized as the TFSA- salt. XX Abstract The TGA, DSC, density, viscosity, conductivity, and molar conductivity properties for the ILs were measured where possible. The viscosity and conductivity data was fitted for the Arrhenius and Vogel-Fulcher Tamman equations. The entire tac-based ILs lie below the KCl ideal line in Walden plot. A fragility plot was obtained by fitting the viscosity data and all the tac-based ILs were fragile. The crystal structures of [C₃(NPhH)₃]TFSA, [C₃(NEt₂)₃]FeCl₄ and [HC₃(NMe₂)4]Cl.2CH₃Cl were determined.
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Roberts, Nicola Jean. "Biocatalytic routes to the synthesis of chiral pharmaceutical intermediates in ionic liquids." Thesis, University College London (University of London), 2005. http://discovery.ucl.ac.uk/1446552/.

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The main objective of this thesis is to identify a generic approach for the application of ionic liquids to bioconversions. Key factors for the operation of bioconversions in ionic liquids have been identified and product recovery options investigated. Two bioconversions were examined. The first was the hydrolytic resolution of racemic 2,3,4,5-tetrahydro-4-methyl-3-oxo-lH-l ,4-benzodiazepine-2-acetic acid methyl ester (SB-235349) to (2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-lH-l,4- benzodiazepine-2-acetic acid (SB-240101) by immobilised Candida antarctica lipase B, CALB (Novozyme 435), performed industrially in t-butanol. Initial studies showed this reaction occurred in several ionic liquids with different physico-chemical properties. Simply replacing the organic solvent with an ionic liquid under otherwise identical conditions reduced the rate of conversion and overall yield. The key factors influencing the rate and yield of this bioconversion in ionic liquids were the type of ionic liquid and the substrate solubility, the reaction temperature and the water content. The final optimised reaction in ionic liquids shows an eighteen-fold enhancement in product formation compared to the optimised t-butanol system. In order for ionic liquids to be applied commercially there are still many issues which still need to be resolved these include: the extraction of substrates and products from the ionic liquid media for down stream processing, and the recycle of the media for subsequent reactions. The next step having optimised the CALB bioconversion of SB- 235349 in ionic liquid media was to extract the SB-240101 product and the un-reacted SB-235349 substrate in order to recycle the ionic liquid. The SB-240101 produced by the reaction was removed by liquid-liquid extraction with 50mM bicarbonate buffer (pH 10); overall 93% of the SB-240101 produced was removed from the ionic liquid into the aqueous buffer phase. The un-reacted 2,3,4,5-tetrahydro-4-methyl-3-oxo-lH- 1,4-benzodiazepine-2-acetic acid methyl, ester (SB-240098) was removed by liquid- liquid extraction with isopropyl alcohol, and 91% was removed from the ionic liquid. The ionic liquid was then regenerated with sodium hydroxide for recycle. The results from the bioconversion with fresh and recycled ionic liquid were almost identical, in both cases around l.8g.L-1 of product was produced in 6 hours. The two-phase extractions were subsequently studied in the Lewis cell, and the mass transfer rate (K0) examined for the extraction of both the substrate and the product from the ionic liquid. Values of K0 determined in the Lewis cell over the Reynolds number range for which a flat, non-perturbed, interface could be maintained were in the range 1.0 - 3.5 X 10-6 m.s-1 for both product and substrate extraction. In both extraction experiments there was a linear increase in K0 with Reynolds number. The second bioconversion the thymidine phosphorylase catalysed synthesis of thymidine from thymine, which is traditionally performed in aqueous media, was then examined in ionic liquids. Initial investigations of this conversion step showed that replacing the aqueous media with an ionic liquid like [BMIM][PF6] under otherwise identical reaction conditions reduced the overall yield, which is attributed to the low solubility of the reagents in this ionic liquid. As the first constraint of the aqueous system was the solubility of the substrates and products; work then focused on those ionic liquids that showed a high solubility for thymine and especially thymidine. A study of the conversion in these high solubility ionic liquids showed conversion to the same degree as that demonstrated in aqueous media. An examination of product recovery from [EMIM][tosylate] following the thymidine transformation showed that the most likely method of product recovery was adsorption to an anion exchange resin 1-X8. In summary the results presented in this thesis show that ionic liquids offer significant advantages as alternative reaction media in industrial bioconversions. These are related to the excellent solvation properties of ionic liquids, and the tunable physicochemical properties of ionic liquids such as miscibility (or immiscibility) with water by changes in the anion or cation. Overall this thesis has identified generic procedures for the design of bioconversions and product recovery options in ionic liquids that have been exemplified using two different bioconversion systems.
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Yu, Jianguo. "Novel chiral phosphonium ionic liquids as solvents and catalysts for cycloadditions : investigation of the Diels-Alder reaction of a series of dienes and dienophiles in novel chiral phosphonium ionic liquids." Thesis, University of Bradford, 2009. http://hdl.handle.net/10454/4307.

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The use of ionic liquids (ILs) as both reagents and solvents is widely recognised. ILs offer a number of advantages compared to regular molecular solvents. These advantages include: chemical and thermal stability, no measurable vapour pressure, no or lower toxicity, non-flammability, catalytic ability, high polarity and they can be recycled. There are a number of research groups investigating the various applications of this reaction medium and most studies have focused on solvents derived from the imidazolium cation. The use of the imidazolium-based ILs in the Diels-Alder reaction has been studied in detail and higher yields compared to conventional methods have been reported. The IL affects the rate and interesting selectivities have been observed. However, not much attention has been paid to the scope and limitations of phosphonium ILs (PILs). Therefore the focus of this thesis is the synthesis and application of novel chiral PILs as environmentally benign, task-specific solvents for the Diels-Alder reaction. In addition, this research seeks alternative ways to eliminate the use of toxic heavy metal catalysts and to exploit methodologies which reduce the energy consumption of the Diels-Alder reaction. A series of CILs were synthesised from the chiral pool and they were characterised by thermogravimetric analysis, differential scanning calorimetry and spectroscopy. They were then investigated as solvents and catalysts in the Diels-Alder reactions of a series of dienes (cyclopentadiene, isoprene, 2,3-dimethylbuta-1,3-diene, furan, pyrrole, N-methyl pyrrole) and dienophiles (methyl acrylate, methyl vinyl ketone, acrylonitrile, dimethyl maleate, acrolein, dimethylacetylene dicarboxylate, maleic anhydride and maleimide). Investigation of the effect of PILs in the presence of three heterogeneous catalysts Al2O3, SiO2 and K-10 montmorillonite were studied. Ultrasound and microwave-assisted Diels-Alder reactions in the PILs, in the absence and presence of the catalysts, were also studied. The reactions of these prototypical substrates illustrated that the solvents are indeed task-specific.
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Sintra, Tânia Ereira. "Synthesis of more benign ionic liquids for specific applications." Doctoral thesis, Universidade de Aveiro, 2017. http://hdl.handle.net/10773/22516.

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Doutoramento em Química
Nas últimas décadas, os líquidos iónicos (ILs) têm sido alvo de elevado interesse quer por parte da academia como a nível industrial. Isto deve-se em grande parte às suas propriedades únicas, assim como à possibilidade de, através de uma apropriada combinação dos seus iões, ser possível ajustar as suas propriedades para uma dada aplicação. Assim, os ILs têm vindo a ser considerados uma abordagem inovador para a “Química verde” e para a sustentabilidade. Contudo, a sua solubilidade em água faz com que estes possam facilmente chegar ao ecossistema aquático, podendo representar um perigo para este. O principal objetivo deste trabalho é estudar novos ILs, mais sustentáveis, assim como algumas das suas potenciais aplicações. Assim, foram investigados ILs como sendo antioxidantes, seletores quirais, hidrótopos, surfactantes, compostos magnéticos, assim como novos compostos hidrofóbicos. Para cada classe de ILs, foi estudada a sua síntese, caracterização físico-química e perfil de ecotoxicidade. Os novos ILs antioxidantes preparados neste trabalho foram avaliados quanto à sua solubilidade em água, estabilidade térmica, citotoxicidade e ecotoxicidade. Foram também estudados vários ILs quirais, quer baseados em aniões quirais (derivados de vários aminoácidos e do ácido tartárico), quer em catiões quirais (derivados da quinina, L-prolina e L-valina), no que respeita à sua estabilidade térmica, rotação ótica e ecotoxicidade. Além disso, foi avaliado o impacto de diferentes estruturas químicas dos ILs, assim como da sua concentração, na solubilidade de fármacos com reduzida solubilidade em água, a fim de analisar o seu comportamento enquanto hidrótopos cataniónicos. Entre as estruturas mais hidrofóbicas referidas neste trabalho estão vários ILs com natureza surfactante e um IL hidrofóbico baseado no anião per-fluoro-tertbutóxido. Relativamente aos ILs com carácter surfactante, foram preparados ILs pertencentes à família dos imidazólios, amónios quaternários e fosfónios, sendo posteriormente avaliados quanto à sua natureza de agregação, propriedades térmicas, ecotoxicidade, e à sua capacidade em promover disrupção celular. Por sua vez, o IL baseado no anião per-fluoro-tert-butóxido foi estudado relativamente às suas propriedades físicas, tais como a sua densidade, viscosidade e tensão superficial, assim como à sua toxicidade. Por fim, 24 ILs magnéticos foram preparados conjugando o catião colínio com diferentes aniões magnéticos ([FeCl4]-, [MnCl4]2-, [CoCl4]2- and [GdCl6]3-), sendo seguidamente avaliados quanto à sua ecotoxicidade. Visando o desenho racional de novos ILs, foi desenvolvido um modelo preditivo QSAR, onde foram utilizandos os dados de ecotoxicidade medidos neste trabalho. As previsões deste modelo relativamente à não toxicidade de um certo número de novos ILs foram testadas com êxito através da síntese destes compostos e posterior avaliação da sua ecotoxicidade utilizando o bioensaio Microtox.
Due to their unique properties, ionic liquids (ILs) have attracted an increased scientific and industrial attention in the last decades. The possibility of tailoring their properties for a specific task by the adequate combination of their ions, makes these ionic compounds good candidates for a wide range of different applications. Actually, ILs have been described as an innovative approach to the “Green Chemistry” and sustainability principles. However, their solubility in water allows their easy access to the aquatic compartment, which makes them potentially hazardous compounds to aquatic organisms. The main goal of this work is to study new, more environmental friendly, IL structures and their main applications. ILs as antioxidants, chiral selectors, hydrotropes, surface-active compounds, with magnetic properties, as well as, new hydrophobic compounds are investigated. The synthesis, physico-chemical characterization and ecotoxicity profile were studied for the various classes of task specific ILs evaluated. New cholinium-based ILs with antioxidant nature were studied regarding their solubility in water, thermal stability, cytotoxicity, and ecotoxicity. Moreover, a large range of chiral ILs (CILs) based on several chiral anions (derived from chiral amino acids and tartaric acid) and chiral cations (based on quinine, L-proline and L-valine), was investigated and their thermal stability, optical rotation and ecotoxicity evaluated. Furthermore, the impact of different ILs structures and concentrations on the solubility of poorly water-soluble drugs was studied, and their role as catanionic hydrotropes investigated. Among the most hydrophobic structures reported in this work are several surface-active ILs and a hydrophobic IL based on the per-fluoro-tert-butoxide anion. The tensioactive ILs, belonging to the imidazolium, quaternary ammonium and phospholium families were tested in terms of their aggregation behavior, thermal properties, ecotoxicity, and their capacity to promore cell disruption. On the other hand, the per-fluoro-tert-butoxide-based IL was evaluated regarding its physical properties, such as density, viscosity, and surface tension and toxicity. Finally, 24 magnetic ILs belonging to the cholinium family and using [FeCl4]-, [MnCl4]2-, [CoCl4]2- and [GdCl6]3- as anions were investigated and their ecotoxicity evaluated. Aiming at the rational design of ILs, a predictive QSAR model was developed with our help, and using ecotoxicity data measured in this work. The predictions of this model concerning the non-toxicity of a number of novel ILs were successfully tested by synthesizing these compounds and evaluating their toxicity using the Microtox bioassay.
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Kim, Hannah. "The synthesis and purification of Chiral Amino Acid Ionic Liquids and Investigation of Quantitative Solvent-Solute Interactions." Thesis, Imperial College London, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.486364.

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This project divides into two halves: the synthesis, purification and characterisation of numerous ionic liquids including amino acid based chiral ionic liquids and polarity studies, which have been undertaken to further the understanding and quantification ofthe solvent-solute interactions by use of Kalmet-Taft measurements. In the early 1980s, the introduction of cleaner technologies to eliminate or significantly reduce hazardous waste generation became a major concern. In particular, a high priority to find alternatives to volatile organic compounds (VOC's), which were found to be very damaging solvents, was realised. Ionic liquids (IL's) remained a curiosity until recently, when the chemists discovered that it was possible to replace the VOC's with IL's and in some cases, the reactions were much improved. Since then, the field of IL's has exploded, which led to a vast increase in the number of publications and in the number of groups throughout the world who have started to work in the field. This project has reviewed some of the synthesis, purification and characterisation of chiral amino acid ILs and improved upon these procedures. The second halfofthe project involved investigating the overall solvating ability some of these purified IL's to obtain a better understanding ofhow these solvents may affect a reaction. This ability is not dependant on one particular physical measurement of the solvent, but is rather a sum ofall the specific and non-specific interactions that might occur between a solvent and solute. A large number of interactions are involved; these could include columbic, directional, inductive, dispersion, hydrogen-bonding, and electron pair donor/acceptor forces. The polarity ofthe IL's and mixtures of ILs with water or dichloromethane were investigated using UV dyes.
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Kholany, Mariam Achraf Mohamed Bahie El Din El. "Enantioselective separation of chiral compounds using aqueous biphasic systems and solid-liquid biphasic system." Master's thesis, Universidade de Aveiro, 2017. http://hdl.handle.net/10773/22708.

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Mestrado em Biotecnologia - Industrial e Ambiental
Tipicamente, apenas um dos enantiómeros é responsável pelo efeito pretendido de um fármaco, sendo que o outro pode levar a respostas menos potentes ou até mesmo indesejadas. As entidades reguladoras praticam políticas restritas em relação à comercialização de fármacos como misturas racémicas. Assim, a indústria farmacêutica tem enfrentado desafios relacionados com o desenvolvimento de métodos para produção de fármacos oticamente puros. No entanto, e considerando a dificuldade acrescida na produção de enantiómeros puros por síntese direta, a síntese de misturas racémicas seguida da sua purificação surge como uma alternativa mais barata, simples e flexível. Os sistemas aquosos bifásicos (SABs) e os sistemas de duas fases sólida-líquida (SDFSL) são técnicas alternativas mais biocompatíveis que têm sido utilizados como técnicas de separação enantiosseletiva de fármacos e/ou aminoácidos com enantiosseletividades bastante promissoras. Para além disso, apresentam benefícios de custo, rapidez, simplicidade e versatilidade de operação e possibilidade de aumento de escala. Este trabalho foca-se no desenvolvimento de SABs e SDFSL constituídos por seletores quirais que possam atuar simultaneamente como solvente. Numa primeira abordagem o objetivo foi desenvolver novos SABs quirais, mais biocompatíveis, simples e eficientes. Para tal, SABs constituídos por açúcares, aminoácidos e líquidos iónicos quirais foram aplicados na resolução enantiomérica de ácido mandélico racémico. O sistema mais promissor, composto por [C1Qui][C1SO4] + K3PO4, obteve um excesso enantiomérico de -33.4%. Numa segunda abordagem, foi possível criar uma alternativa mais simples e mais eficiente recorrendo a SDFSL. Com estes sistemas, foi obtido o valor mais elevado de excesso enantiomérico deste trabalho, de 49.0%, através da precipitação enantiosseletiva do R-ácido mandélico por interação com [N4444][D-Phe].
Conventionally, only one of the enantiomers is responsible for the intended effect of a drug, whilst the other may lead to a less potent or even undesired response. Regulation entities are very strict regarding the commercialization of racemic drugs. Thus, pharmaceutical industry has been facing challenges related to the creation of methods to produce optically active drugs. However, considering the increased difficulty in the production of pure enantiomers by direct synthesis, the synthesis of racemic mixtures followed by their purification appears as a cheaper, simpler and more flexible alternative. Aqueous biphasic systems (ABS) and solid-liquid biphasic system (SLBS) are more biocompatible alternatives that have been used to separate racemic drugs and amino acids with promising enantioselectivities. Furthermore, these are cost-effective, quick, simple and operationally flexible. This work intended to develop ABS and SLBS using chiral selectors that can simultaneously act as solvents. In a first attempt, chiral ABS of better biocompatibility, simplicity and efficiency were developed. For that purpose, ABS constituted by sugars, amino acids and chiral ionic liquids (CILs) were applied for chiral resolution of racemic mandelic acid (MA). The most promising ABS was a system composed of [C1Qui][C1SO4] + K3PO4 which yielded the maximum enantiomeric excess of -33.4%. In a second approach, it was possible to create a simpler and more efficient technique resorting to SLBS. The enantiomeric excess value of 49.0% was achieved, by the enantioselective precipitation of the R-MA caused by interactions with [N4444][D-Phe].
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Wang, Ying. "Chiral ionic liquid in chiral separation and catalysis." Thesis, Queen's University Belfast, 2013. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.603555.

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In this thesis, the results of synthesis of chiral ionic liquids (ILs) and an investigation of their application in chiral separation and catalysis are described. The study of the chiral lLs application was performed using liquid-liquid extraction, crystallization and asymmetric catalysis with analysis of substrate content and enantioselectivity by High Performance Liquid Chromatography (HPLC) . A series of chiral lLS with chiral cations or chiral anions were synthesized through alkylation or anion exchange with optical pure starting materials as the •chiral pool", Properties of chiral ILS made in house were studied using various techniques, The structures and configurations of the chiral ILs can be altered easily to meet the required physical properties, such as melting point and viscosity, Chiral! ILs made in house show chiral affinity with a range of racemic compounds, In the liquid-liquid extraction of menthol from chiral lL, good extraction is observed from the chiral lL layer into alkane !layer without visible leaching of the chiral lL into the alkane layer. In the mandelic acid resolution by • Dutch resolution", 22 different ILS were used as additive in the chiral selector, In general, ILS exhibit a equalize effect on both yield and ee of the final product. For the asymmetric catalysis study, both Mukaiyama-aldol reaction and Diels-Alder reaction were investigated with Cu(II)-PhBOX and Zn(II)-PhBOX as catalyst. In the Mukaiyama-aldol reaction, chiral ILS can be applied . as ligand and an increased ee is observed as compared with the reactions in the absence of the Il. In the Diels-Alder reaction, addition of the chiral Il 19 (Il of (1R,2S.5R)- menthol) with Zn(II)-PhBOX led to an increase in the endo ee from 5 % in DCM, 68 % in ether and 57 % in pure (C 2mim][NH 10 91 % under homogeneous reaction condition and 95 % in biphasic system with both high conversion and high endo selectivity. The endo selectivity of biphasic system with the chiral lL 1 g, [C2mim][NTf21 and ether is 99 %, which means nearly all product goes into endo form with 95 % ee.
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Book chapters on the topic "Chiral ionic liquids"

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Hu, Rongjing, and Lei Yang. "Chiral Ionic Liquids." In Encyclopedia of Ionic Liquids, 1–15. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-10-6739-6_130-1.

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Gaumont, Annie-Claude, Yves Génisson, Frédéric Guillen, Viacheslav Zgonnik, and Jean-Christophe Plaquevent. "Chiral Ionic Liquids for Asymmetric Reactions." In Catalytic Methods in Asymmetric Synthesis, 323–44. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2011. http://dx.doi.org/10.1002/9781118087992.ch7.

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Vasiloiu, Maria, and Katharina Bica. "Chiral Ionic Liquids in Separation Sciences." In Green Chemistry and Sustainable Technology, 167–92. Berlin, Heidelberg: Springer Berlin Heidelberg, 2015. http://dx.doi.org/10.1007/978-3-662-48520-0_8.

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Li, Min, David K. Bwambok, Sayo O. Fakayode, and Isiah M. Warner. "Chiral Ionic Liquids in Chromatographic Separation and Spectroscopic Discrimination." In Chiral Recognition in Separation Methods, 289–329. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/978-3-642-12445-7_11.

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Engel, Robert, Sharon Lall-Ramnarine, Delroy Coleman, and Marie Thomas. "New Cations for Ionic Liquids, Including Chiral Adjuncts with Phosphate and Sulfonylimide Anions." In ACS Symposium Series, 259–66. Washington, DC: American Chemical Society, 2007. http://dx.doi.org/10.1021/bk-2007-0950.ch020.

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Xu, Lijin, Kim Hung Lam, Jiwu Ruan, Qinghua Fan, and Albert S. C. Chan. "Ruthenium Catalyzed Asymmetric Hydrogenation of α- and β-Ketoesters in Room Temperature Ionic Liquids Using Chiral P-Phos Ligand." In ACS Symposium Series, 224–34. Washington, DC: American Chemical Society, 2007. http://dx.doi.org/10.1021/bk-2007-0950.ch017.

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Itoh, Toshiyuki, Yoshikazu Abe, Takuya Hirakawa, Nagisa Okano, Shino Nakajima, Shuichi Hayase, Motoi Kawatsura, Tomoko Matsuda, and Kaoru Nakamura. "Chiral Pyrrolidine-Substituted Ionic Liquid-Mediated Activation of Enzyme." In ACS Symposium Series, 155–67. Washington, DC: American Chemical Society, 2010. http://dx.doi.org/10.1021/bk-2010-1038.ch013.

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Masson, G., and J. Zhu. "Reaction in Chiral Ionic Liquids." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00405.

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Liu, Yong, Jiajian Peng, Shangru Zhai, Ningya Yu, Meijiang Li, Jianjiang Mao, Huayu Qiu, Jianxiong Jiang, and Guoqiao La. "One-pot synthesis of ionic liquid functionalized SBA-15 mesoporous silicas." In Recent Progress in Mesostructured Materials - Proceedings of the 5th International Mesostructured Materials Symposium (IMMS2006), Shanghai, P.R. China, August 5-7, 2006, 127–30. Elsevier, 2007. http://dx.doi.org/10.1016/s0167-2991(07)80281-3.

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Sarkar, M. S., Ji-Young Jung, and Myung-Jong Jin. "VO(acac)2 incorporated in mesoporous silica SBA-15-conflned ionic liquid as a catalyst for epoxidation." In Recent Progress in Mesostructured Materials - Proceedings of the 5th International Mesostructured Materials Symposium (IMMS2006), Shanghai, P.R. China, August 5-7, 2006, 713–16. Elsevier, 2007. http://dx.doi.org/10.1016/s0167-2991(07)80420-4.

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Conference papers on the topic "Chiral ionic liquids"

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Harrison, Benjamin, Richard Czerw, Manohar S. Konchady, Devdas M. Pai, Matt W. Lopatka, and Paul B. Jones. "Ionic Liquids Incorporating Nanomaterials as Lubricants for Harsh Environments." In ASME 2005 International Mechanical Engineering Congress and Exposition. ASMEDC, 2005. http://dx.doi.org/10.1115/imece2005-81680.

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Ionic liquids are salts that are liquid at ambient temperatures, and they produce virtually no hazardous vapors. As lubricating liquids, ionic liquid lubricants are of interest for reducing wear in circumstances where conventional lubricants are impractical such as in aerospace applications and high temperature vacuum bearings. The synthetic flexibility of ionic liquids allows control of the liquidous temperature range, good polymer compatibility, and high thermal stability. In this paper, a variety of ionic liquids were synthesized to build a library for testing. The liquids were thermally characterized by DSC and TGA, and mechanically characterized by pin-on-disk and 4-ball testing. Several chiral ionic liquids were synthesized as candidates for MEMS testing. The chiral nature of the liquids should help prevent crystallization in MEMs applications. Additionally, nanomaterials incorporated into the lubricants imparted lower friction coefficients and enhanced thermal stability.
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Vo-Thanh, Giang, and Thu Truong-Thi-Kim. "Synthesis of Functionalized Chiral Ammonium, Imidazolium and Pyridinium-based Ionic Liquids derived from (-)-Ephedrine using solvent-free microwave activation. Applications for the Asymmetric Michael Addition." In The 17th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2013. http://dx.doi.org/10.3390/ecsoc-17-f003.

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Hirade, Tetsuya. "Positronium bubble oscillation in room temperature ionic liquids." In 2nd Japan–China Joint Workshop on Positron Science (JWPS2013). Japan Society of Applied Physics, 2014. http://dx.doi.org/10.7567/jjapcp.2.011003.

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Chen, Liang, Rundong Jia, Qianqian Huang, and Ru Huang. "Si/SnS2 Vertical Heterojunction Tunneling Transistor with Ionic-Liquid Gate for Ultra-Low Power Application." In 2021 China Semiconductor Technology International Conference (CSTIC). IEEE, 2021. http://dx.doi.org/10.1109/cstic52283.2021.9461446.

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