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Synthesis of novel room temperature chiral ionic liquids: application as reaction media for the heck arylation of aza-endocyclic acrylates
Pastre, Julio C.;Génisson, Yves;Saffon, Nathalie;Dandurand, Jany;Correia, Carlos R. D.;
Journal of the Brazilian Chemical Society , 2010, DOI: 10.1590/S0103-50532010000500009
Abstract: new achiral and chiral rtils were prepared using novel and/or optimized synthetic routes. these new series of imidazolinium, imidazolium, pyridinium and nicotine-derived ionic liquids were fully characterized including differential scanning calorimetry (dsc) analysis. the performance of these achiral and chiral room temperature ionic liquids (rtils) was demonstrated by means of the heck arylation of endocyclic acrylates employing arenediazonium salts and aryl iodides. the heck arylations performed in the presence of these ionic entities, either as a solvent or as an additive, were effective leading to complete conversion of the substrate and good to excellent yield of the heck adduct. in spite of the good performances, no asymmetric induction was observed in any of the cases studied. two new diastereoisomeric nhc-palladium complexes were prepared in good yields from a chiral imidazolium salt and their structure characterized by x-ray diffraction. overall, the heck arylations employing arenediazonium tetrafluoroborates in rtils were more effective than the traditional protocols employing aryl iodides in terms of reactivity and yields.
Moisture Stable Ambient Temperature Ionic Liquids: Solvents for the New Millennium. 1. The Heck Reaction  [PDF]
Joshua Howarth,Andrea Dallas
Molecules , 2000, DOI: 10.3390/50600851
Abstract: In this paper we report examples of the Heck reaction in the new moisture stable ambient temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF6). We have found that the yield of product is comparable with Heck reactions carried out in DMF, the conventional solvent for this reaction, and that the ionic liquid/catalyst mixture can be recycled several times.
Progress in Imidazolium Ionic Liquids Assisted Fabrication of Carbon Nanotube and Graphene Polymer Composites  [PDF]
Rengui Peng,Yuanzhen Wang,Wei Tang,Yingkui Yang,Xiaolin Xie
Polymers , 2013, DOI: 10.3390/polym5020847
Abstract: Carbon nanotubes (CNTs) and graphene sheets are the most promising fillers for polymer nanocomposites due to their superior mechanical, electrical, thermal optical and gas barrier properties, as well as high flame-retardant efficiency. The critical challenge, however, is how to uniformly disperse them into the polymer matrix to achieve a strong interface for good load transfer between the two. This problem is not new but more acute in CNTs and graphene, both because they are intrinsically insoluble and tend to aggregate into bundles and because their surfaces are atomically smooth. Over the past decade, imidazolium ionic liquids (Imi-ILs) have played a multifunctional role (e.g., as solvents, dispersants, stabilizers, compatibilizers, modifiers and additives) in the fabrication of polymer composites containing CNTs or graphene. In this review, we first summarize the liquid-phase exfoliation, stabilization, dispersion of CNTs and graphene in Imi-ILs, as well as the chemical and/or thermal reduction of graphene oxide to graphene with the aid of Imi-ILs. We then present a full survey of the literature on the Imi-ILs assisted fabrication of CNTs and graphene-based nanocomposites with a variety of polymers, including fluoropolymers, hydrocarbon polymers, polyacrylates, cellulose and polymeric ionic liquids. Finally, we give a future outlook in hopes of facilitating progress in this emerging area.
Use of ionic liquids in biodiesel production: a review
Andreani, L.;Rocha, J. D.;
Brazilian Journal of Chemical Engineering , 2012, DOI: 10.1590/S0104-66322012000100001
Abstract: this paper discusses the feasibility of the use of ionic liquids as catalysts in the biodiesel production field, describing some studies already published in the literature on this theme. ionic liquids are regarded as a new generation of catalysts in the chemical industry, with several uses in different commercial segments. however only a few publications involving this topic can be found in the literature addressing the manufacture of biodiesel from vegetable oils or animal fats. through the analysis of the data generated in the studies reviewed, it is possible to affirm that ionic liquids present great potential as catalysts for biodiesel production, but there are some challenges to be faced, such as the production of ionic liquids with low cost, easy recovery and with the possibility of reutilization of the catalyst for several cycles.
Carbon-Carbon Cross Coupling Reactions in Ionic Liquids Catalysed by Palladium Metal Nanoparticles  [PDF]
Martin H. G. Prechtl,Jackson D. Scholten,Jairton Dupont
Molecules , 2010, DOI: 10.3390/molecules15053441
Abstract: A brief summary of selected pioneering and mechanistic contributions in the field of carbon-carbon cross-coupling reactions with palladium nanoparticles (Pd-NPs) in ionic liquids (ILs) is presented. Five exemplary model systems using the Pd-NPs/ILs approach are presented: Heck, Suzuki, Stille, Sonogashira and Ullmann reactions which all have in common the use of ionic liquids as reaction media and the use of palladium nanoparticles as reservoir for the catalytically active palladium species.
Vapor Pressure of Ionic Liquids  [PDF]
Markus Bier,S. Dietrich
Physics , 2010, DOI: 10.1080/00268971003604609
Abstract: We argue that the extremely low vapor pressures of room temperature ionic liquids near their triple points are due to the combination of strong ionic characters and of low melting temperatures.
Qijun Wang,Yuanxin Wu,Shengdong Zhu
BioResources , 2011,
Abstract: Cellulosic ethanol production has drawn much attention in recent years. However, there remain significant technical challenges before such production can be considered as economically feasible at an industrial scale. Among them, the efficient conversion of carbohydrates in lignocellulosic biomass into fermentable sugars is one of the most challenging technical difficulties in cellulosic ethanol production. Use of ionic liquids has opened new avenues to solve this problem by two different pathways. One is pretreatment of lignocellulosic biomass using ionic liquids to increase its enzymatic hydrolysis efficiency. The other is to transform the hydrolysis process of lignocellulosic biomass from a heterogeneous reaction system to a homogeneous one by dissolving it into ionic liquids, thus improving its hydrolysis efficiency.
Ahmad Adlie Shamsuri,Dzulkefly Kuang Abdullah
Makara Seri Sains , 2010,
Abstract: Ionic liquids are considered as an ideal alternative to volatile organic solvents and chemical industries in the future,because they are non-volatile. Ionic liquids are also considered as new novel chemical agents and widely regarded as agreener alternative to many commonly used solvents. Ionic liquids have been studied for a wide range of syntheticapplications and have attracted considerable interest for use as electrolytes in the areas of organic synthesis, catalysis,solar cell, fuel cells, electrodeposition and supercapacitors. However, some ionic liquids suffer from more or less somedrawbacks such as toxicity, preparation and high cost in the process for use. Most recently, three types of ionic liquidsare attracted much attentions specifically traditional ionic liquid, protic ionic liquid and deep eutectic solvent, wheretheir preparation, mechanism and limitation were differentiated. However, those liquids are having their ownadvantages and limitations based on applications. Traditional ionic liquid and protic ionic liquid are highly cost andtoxic for applied engineering research, but they consist of micro-biphasic systems composed of ionic compounds whichhave more varieties in the applications. The deep eutectic solvent is very economic for large-scale possessing but thereare only limited ionic mixtures to certain application such as electrochemistry.
Ionic Liquids in Tribology  [PDF]
Ichiro Minami
Molecules , 2009, DOI: 10.3390/molecules14062286
Abstract: Current research on room-temperature ionic liquids as lubricants is described. Ionic liquids possess excellent properties such as non-volatility, non-flammability, and thermo-oxidative stability. The potential use of ionic liquids as lubricants was first proposed in 2001 and approximately 70 articles pertaining to fundamental research on ionic liquids have been published through May 2009. A large majority of the cations examined in this area are derived from 1,3-dialkylimidazolium, with a higher alkyl group on the imidazolium cation being beneficial for good lubrication, while it reduces the thermo-oxidative stability. Hydrophobic anions provide both good lubricity and significant thermo-oxidative stability. The anions decompose through a tribochemical reaction to generate metal fluoride on the rubbed surface. Additive technology to improve lubricity is also explained. An introduction to tribology as an interdisciplinary field of lubrication is also provided.
On the Chemical Stabilities of Ionic Liquids  [PDF]
Subbiah Sowmiah,Venkatesan Srinivasadesikan,Ming-Chung Tseng,Yen-Ho Chu
Molecules , 2009, DOI: 10.3390/molecules14093780
Abstract: Ionic liquids are novel solvents of interest as greener alternatives to conventional organic solvents aimed at facilitating sustainable chemistry. As a consequence of their unusual physical properties, reusability, and eco-friendly nature, ionic liquids have attracted the attention of organic chemists. Numerous reports have revealed that many catalysts and reagents were supported in the ionic liquid phase, resulting in enhanced reactivity and selectivity in various important reaction transformations. However, synthetic chemists cannot ignore the stability data and intermolecular interactions, or even reactions that are directly applicable to organic reactions in ionic liquids. It is becoming evident from the increasing number of reports on use of ionic liquids as solvents, catalysts, and reagents in organic synthesis that they are not totally inert under many reaction conditions. While in some cases, their unexpected reactivity has proven fortuitous and in others, it is imperative that when selecting an ionic liquid for a particular synthetic application, attention must be paid to its compatibility with the reaction conditions. Even though, more than 200 room temperature ionic liquids are known, only a few reports have commented their effects on reaction mechanisms or rate/stability. Therefore, rather than attempting to give a comprehensive overview of ionic liquid chemistry, this review focuses on the non-innocent nature of ionic liquids, with a decided emphasis to clearly illuminate the ability of ionic liquids to affect the mechanistic aspects of some organic reactions thereby affecting and promoting the yield and selectivity.
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