APPLICATIONS OF IONIC LIQUIDS IN SCIENCE AND TECHNOLOGY ppt

APPLICATIONS OF IONIC LIQUIDS IN SCIENCE AND TECHNOLOGY Edited by Scott T. Handy Applications of Ionic Liquids in Science and Technology Edited by Scott T. Handy Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia Copyright © 2011 InTech All chapters are Open Access articles distributed under the Creative Commons Non Commercial Share Alike Attribution 3.0 license, which permits to copy, distribute, transmit, and adapt the work in any medium, so long as the original work is properly cited. After this work has been published by InTech, authors have the right to republish it, in whole or part, in any publication of which they are the author, and to make other personal use of the work. Any republication, referencing or personal use of the work must explicitly identify the original source. Statements and opinions expressed in the chapters are these of the individual contributors and not necessarily those of the editors or publisher. No responsibility is accepted for the accuracy of information contained in the published articles. The publisher assumes no responsibility for any damage or injury to persons or property arising out of the use of any materials, instructions, methods or ideas contained in the book. Publishing Process Manager Alenka Urbancic Technical Editor Teodora Smiljanic Cover Designer Jan Hyrat Image Copyright Olivier Le Queinec, 2010. Used under license from Shutterstock.com First published September, 2011 Printed in Croatia A free online edition of this book is available at www.intechopen.com Additional hard copies can be obtained from orders@intechweb.org Applications of Ionic Liquids in Science and Technology, Edited by Scott T. Handy p. cm. ISBN 978-953-307-605-8 free online editions of InTech Books and Journals can be found at www.intechopen.com Contents Preface IX Part 1 Biomass Utilization 1 Chapter 1 Ionic Liquids in Catalytic Biomass Transformation 3 Zhu Yinghuai, Algin Oh Biying, Xiao Siwei, Narayan S Hosmane and John A. Maguire Chapter 2 Biotransformation of Underutilized Natural Resource to Valuable Compounds in Ionic Liquid: Enzymatic Synthesis of Caffeic Acid Phenethyl Ester Analogues from Immature Coffee Beans 27 Atsushi Kurata, Tokio Fujita, and Noriaki Kishimoto Part 2 Electronic Applications 45 Chapter 3 Undeniable Contribution of Aprotic Room Temperature Ionic Liquids in the Security of Li-Ion Batteries 47 Claude-Montigny Bénédicte, Stefan Claudia Simona and Violleau David Chapter 4 Ionic Liquids in Charge Storage Devices: Effect of Purification on Performance 73 John D. Stenger-Smith, Andrew P. Chafin, Clare F. Kline Jr., Gregory S. Ostrom and Roxanne L. Quintana Chapter 5 Polymers with Ionic Liquid Fragments as Potential Conducting Materials for Advanced Applications 83 Santiago V. Luis, Eduardo García-Verdugo, M. Isabel Burguete, Andreu Andrio, Sergio Mollá and Vicente Compan Chapter 6 Ionic Liquids for the Electric Double Layer Capacitor Applications 109 Takaya Sato, Shoko Marukane and Takashi Morinaga Chapter 7 Ionic Liquid Used in Long-Lifetime Polymer Light-Emitting Electrochemical Cells 135 Yan Shao VI Contents Part 3 Polymers 153 Chapter 8 Ionic Liquids Gelation with Polymeric Materials: The Ion Jelly Approach 155 Nuno M.T. Lourenço, Ana V.M. Nunes, Catarina M.M. Duarte and Pedro Vidinha Chapter 9 Environmentally Friendly Synthesis of Polymer-Grafted Nanoparticles 173 Norio Tsubokawa Chapter 10 Ionic Liquids as Porogens in the Synthesis of Molecularly Imprinted Polymers 197 Katherine M Booker, Clovia I Holdsworth, Michael C Bowyer and Adam McCluskey Chapter 11 Magnetorheological Elastomers Containing Ionic Liquids 213 Marcin Masłowski and Marian Zaborski Part 4 Nanomaterials and Metals 233 Chapter 12 Concepts for the Stabilization of Metal Nanoparticles in Ionic Liquids 235 Alexander Kraynov and Thomas E. Müller Chapter 13 Studies Regarding the Nickel Electrodeposition from Choline Chloride Based Ionic Liquids 261 Liana Anicai, Andreea Florea and Teodor Visan Chapter 14 Ionic Liquids as Advantageous Solvents for Preparation of Nanostructures 287 Alexandrina Nan and Jürgen Liebscher Part 5 Separation Methods 309 Chapter 15 Ionic Liquids in Separation Techniques 311 Jolanta Flieger and Anna Czajkowska-Żelazko Chapter 16 Ionic Liquid-Mediated Liquid-Liquid Extraction 343 Qilong Ren, Qiwei Yang, Yan Yan, Huabin Xing, Zongbi Bao, Baogen Su and Yiwen Yang Chapter 17 Liquid Matrices in MALDI-MS 361 Yuko Fukuyama Chapter 18 Ionic Liquids in Separation of Metal Ions from Aqueous Solutions 375 Magdalena Regel-Rosocka and Maciej Wisniewski Contents VII Part 6 Miscellaneous Applications 399 Chapter 19 Inner Filter Effect in the Fluorescence Emission Spectra of Room Temperature Ionic Liquids with-β-Carotene 401 Krzysztof Pawlak, Andrzej Skrzypczak and Grazyna E. Bialek-Bylka Chapter 20 Ionic Liquid Lubricant with Ammonium Salts for Magnetic Media 421 Hirofumi Kondo Chapter 21 Application of Ionic Liquids to Space Propulsion 447 Fahrat Kamal, Batonneau Yann, Brahmi Rachid and Kappenstein Charles Chapter 22 The Latent Application of Ionic Liquids in Absorption Refrigeration 467 Shiqiang Liang, Wei Chen, Keyong Cheng, Yongxian Guo and Xiaohong Gui Chapter 23 Optofluidic Compound Lenses Made with Ionic Liquids 495 Sergio Calixto, Martha Rosete-Aguilar, Francisco J. Sanchez-Marin, Olga L. Torres-Rocha, E. Militza Martinez Prado and Margarita Calixto-Solano Preface Ionic liquids (more specifically, room temperature ionic liquids (RTIL)) have attracted considerable interest over the last several years. Although the specific definition of what is a RTIL varies from person to person, the most generally accepted definition is a salt with a melting point below 100 °C. Such a broad definition leaves considerable room for flexibility, which contributed to labeling RTILs as “designer solvents.” The history of ionic liquids (and the closely related molten salts) has a rather ill- defined beginning, although it is most commonly dated back to 1914 from the work of Walden on the use of alkylammonium nitrates. The next burst of interest occurred with the discovery of chloroaluminates formed by combining quaternary heterocyclic cations with aluminum chloride. These materials exhibited a great deal of potential for use in a variety of areas, but all suffered from extreme sensitivity to moisture. A major step forward was made by Wilkes in the early 1990s, with the report of moisture stable ionic liquids created by replacing the aluminum chloride with other anions, such as tetrafluoroborate or hexafluorophosphate. Since that seminal report by Wilkes and co-workers, the family of RTILs has seen explosive growth. Starting with imidazolium cations, the cationic component has been varied to include pyridinium, ammonium, phosphonium, thiazolium, and triazolium species. In general, these cations have been combined with weakly coordinating anions, although not all weakly coordinating anions result in RTILs (for example, the very weakly coordinating polyhedral borane anions of Reed afford salts with melting points between 45 and 156 °C for a series of imidazolium cations). Common examples include tetrafluoroborate, hexafluorophosphate, triflate, triflimide, and dicyanimide. Of these, the first two have been explored the most extensively, and must be treated with the greatest caution, as they are fairly readily hydrolyzed to boric acid and phosphate respectively. Indeed, various phosphate and phosphinate anions have been employed to some advantage in RTILs and the list of possible anionic components continues to grow at a rapid rate. This volume, which is the second in a two volume set on ionic liquids, focuses on applications of ionic liquids in a growing range of areas. Throughout the 1990s, it seemed that the most attention in the area of ionic liquids applications was directed toward their use as solvents for organic and transition-metal-catalyzed reactions. This X Preface interest certainly continues to the present date, and is touched on in several chapters in volume 1 of the book, but the most innovative uses of ionic liquids span a much more diverse field than just synthesis. Fig. 1. Representative Ionic Liquid Components For example, since ionic liquids are ions, they have been explored for use in various electronic applications, including electrolytes for batteries (Claude-Montigny, Stefan, and Violleau), capacitors and charge storage devices (Takaya, Shoko, and Takashi; Stenger-Smith, Chafin, Kline, Ostrom, and Quintana), as well as conducting and light emitting materials (Shao; and Luius, Garci-Verdugo, Burguete, Andrio, Molla, and Compañ). There is also a list of ways to employ ionic liquids in the area of polymers: as grafted components (Maslowski and Zaborski), as solvents for polymerization (Tsubokawa), as modifiers of polymer morphology (Booker, Holdsworth, Bowyer, and McCluskey), and even as unusual components of polymers (Vidinha, Lourenco, Nunes, Duarte, and Barreiros). Similarly, ionic liquids are finding increasing use in the popular area of nanomaterials. Much of this effort is directed toward using ionic liquids as either solvents for the synthesis of nanomaterials (Nan and Liebscher) or their stabilization (Kraynov and Mueller). Electrodeposition and recovery of metals is a related and fairly mature field (Anicai, Florea, and Visan). A second, more mature area of application for ionic liquids is in the field of separations and spectroscopy (Flieger and Czajkowska-Belazko). For some time, ionic liquids have been explored as matrices for mass spectrometry (MALDI) (Fukuyama). Cation Anion N N N R R R 4 N R 4 P BF 4 PF 6 N(CN) 2 NTf 2 [...]... method 8 Applications of Ionic Liquids in Science and Technology Fig 6 Direct access to functionalized ILs 2.Transformation of polysaccharides to monosaccharides 2.1 Solubility behavior of biomass in ionic liquids Cellulose is made up of a linear chain with several β-(1→4) linked glucose repeating units (Figure 7) They are highly packed together with strong intra and inter hydrogen bonding and van der... 1 Ionic Liquids in Catalytic Biomass Transformation 1Institute Zhu Yinghuai1,*, Algin Oh Biying1, Xiao Siwei1, Narayan S Hosmane2 and John A Maguire3 of Chemical and Engineering Sciences, Jurong Island, Singapore 2Department of Chemistry and Chemical Biology, Northern Illinois University, DeKalb, Illinois 3Department of Chemistry, Southern Methodist University, Dallas, Texas 1Singapore 2,3USA 1 Introduction... cost-effective In spite of the possibilities that are opened up by using ionic liquids in biomass chemistry, both their recovery and reuse for continuous processes remain a formidable challenge for the industrialization of new technologies Ionic liquids are relatively expensive compared to traditional solvents and the high cost of utilizing ionic liquids must be offset; this is mandatory for the development of. .. direct and most efficient starting material for the formation of 5-HMF using old and conventional dehydration methods For industrial application, glucose is converted to fructose using enzymatic hydrolysis 16 Applications of Ionic Liquids in Science and Technology Fig 16 Continuous batch process for the conversion of fructose to 5-HMF in a THF([BMIM][Cl]) biphasic system [33] Therefore, a number of investigations... carbohydrate that consists of fructose units with degrees of polymerization (DP) ranging from 2 to 60 The fructosyl units are linked by β(21) Ionic Liquids in Catalytic Biomass Transformation 19 linkages with the glucose as the terminating unit of the polymer chain [38] Inulins are found in plants such as artichoke tuber and chicory root and stored as energy sources Since inulin-type fructans are resistant... the same degree of polymerization and polydispersity as native cellulose but it 10 Applications of Ionic Liquids in Science and Technology depends largely on the operating conditions of the precipitation Varying the condition of the precipitation can alter the degree of crystallinity of the precipitated cellulose For example, cellulose precipitated after being dissolved in [AMIM][Cl] and [BMIM][Cl]... digestive enzymes in human intestine, they are classified as non-digestible carbohydrates as they [39] Qi et al reported an effective one pot [40], two-step process for the production of 5-HMF using inulin in ionic liquids under mild conditions Combining [BMIM][Cl] and a strong acidic cation exchange resin gave a 5-HMF yield of 55% in 20 min Subsequently, a two-step in one pot system was reported in which two... chemicals from a variety of carbohydrates 20 Applications of Ionic Liquids in Science and Technology The production of 5-HMF and furfural from lignocellulosic biomass (corn stalk, rice straw and pine wood) in ILs, catalyzed by CrCl3 under microwave irradiation, was reported with yields 45-52% and 23-31% respectively, from corn stalk, rice straw and pine wood in less than 3 min (Table 2) [3] This method... selective conversion of fructose Ionic Liquids in Catalytic Biomass Transformation Fig 18 Two possible mechanisms for the dehydration of fructose and isomerization of glucose Fig 19 Proposed metal halide interactions with glucose in [EMIM][Cl] [34] 17 18 Implausible pathway Halide ion acting as a base to form enol via the deprotonation of C-1 Applications of Ionic Liquids in Science and Technology Plausible... processes In addition, the technology available now shows that ionic liquids can only dissolve about 10-15 wt % cellulose to give very thick and viscous solutions at these low concentrations The future of R&D for biomass processing utilizing ionic liquids relies on the development of novel, environmentally-friendly ionic liquids that allow high concentrations of dissolved 24 Applications of Ionic Liquids in . APPLICATIONS OF IONIC LIQUIDS IN SCIENCE AND TECHNOLOGY Edited by Scott T. Handy Applications of Ionic Liquids in Science and Technology Edited by Scott T. Handy. Bowyer, and McCluskey), and even as unusual components of polymers (Vidinha, Lourenco, Nunes, Duarte, and Barreiros). Similarly, ionic liquids are finding increasing use in the popular area of nanomaterials Yinghuai 1, *, Algin Oh Biying 1 , Xiao Siwei 1 , Narayan S Hosmane 2 and John A. Maguire 3 1 Institute of Chemical and Engineering Sciences, Jurong Island, Singapore 2 Department of Chemistry and Chemical