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1-Alkyl-3-Methylimidazolium Bis(Pentafluoroethylsulfonyl)Imide Based Ionic Liquids: a Study of Their Physical and Electrochemical Properties

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1-Alkyl-3-Methylimidazolium Bis(Pentafluoroethylsulfonyl)Imide Based Ionic Liquids: a Study of Their Physical and Electrochemical Properties Wright State University CORE Scholar Browse all Theses and Dissertations Theses and Dissertations 2008 1-alkyl-3-methylimidazolium Bis(pentafluoroethylsulfonyl)imide Based Ionic Liquids: A Study of Their Physical and Electrochemical Properties Jennifer N. DeCerbo Wright State University Follow this and additional works at: https://corescholar.libraries.wright.edu/etd_all Part of the Chemistry Commons Repository Citation DeCerbo, Jennifer N., "1-alkyl-3-methylimidazolium Bis(pentafluoroethylsulfonyl)imide Based Ionic Liquids: A Study of Their Physical and Electrochemical Properties" (2008). Browse all Theses and Dissertations. 854. https://corescholar.libraries.wright.edu/etd_all/854 This Thesis is brought to you for free and open access by the Theses and Dissertations at CORE Scholar. It has been accepted for inclusion in Browse all Theses and Dissertations by an authorized administrator of CORE Scholar. For more information, please contact [email protected]. 1-ALKYL-3-METHYLIMIDAZOLIUM BIS(PENTAFLUOROETHYLSULFONYL)IMIDE BASED IONIC LIQUIDS: A STUDY OF THEIR PHYSICAL AND ELECTROCHEMICAL PROPERTIES A thesis submitted in partial fulfillment of the requirements of the degree of Master of Science By JENNIFER NICOLE DECERBO B.S. Wittenberg University, 2006 2008 Wright State University WRIGHT STATE UNIVERSITY SCHOOL OF GRADUATE STUDIES July 2, 2008 I HEREBY RECOMMEND THAT THE THESIS PREPARED UNDER MY SUPERVISION BY Jennifer Nicole DeCerbo ENTITLED 1-Alkyl-3-Methylimidazolium bis(pentafluoroethylsulfonyl)imide Based Ionic Liquids: A Study of Their Physical and Electrochemical Properties BE ACCEPTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF Master of Science. _______________________________ Vladimir Katovic, Ph.D. Thesis Director ______________________________ Kenneth Turnbull, Ph.D. Department Chair Committee on Final Examination _______________________________ Vladimir Katovic, Ph.D. _______________________________ William A. Feld, Ph.D. _______________________________ David A. Grossie, Ph.D. _______________________________ Joseph F. Thomas, Jr., Ph.D. Dean, School of Graduate Studies ii ABSTRACT DeCerbo, Jennifer Nicole. M.S., Department of Chemistry, Wright State University, 2008. 1-Alkyl-3-Methylimidazolium bis(pentafluoroethylsulfonyl)imide Based Ionic Liquids: A Study of Their Physical and Electrochemical Properties. Ionic liquids are an attractive possibility for battery electrolytes. Five ionic liquids were synthesized using a 1-alkyl-3-methylimidazolium (XMI+) cation, where the alkyl group was ethyl, propyl, butyl, pentyl, or hexyl, and a bis(pentafluoroethyl- sulfonyl)imide (Beti-) anion. The absorption and desorption of water, conductivities, densities, viscosities, decomposition temperatures, and electrochemical properties were studied. These ionic liquids were found to absorb less water than previously studied - - ionic liquids with tetrafluoroborate (BF4 ) and hexafluorophosphate (PF6 ) anions. Their conductivities decreased with longer alkyl chains on the imidazolium cation and were - lower than ionic liquids with BF4 as the anion. The densities of the ionic liquids decreased with increasing temperature and alkyl chain length. Viscosities decreased with increasing temperature but increased with increasing chain length. All of the ionic liquids were found to be thermally stable to nearly 400 oC. The potential windows increased with increasing chain length, from 4.2 V (EMIBeti) to 4.7 V (HMIBeti). iii TABLE OF CONTENTS Page I. Introduction ...........................................................................................................1 Molten Salts and Ionic Liquids .....................................................................1 Haloaluminate Ionic Liquids .............................................................2 Non-Chloroaluminate Room Temperature Ionic Liquids .................4 Ionic Liquids as Green Solvents ...................................................................5 Separations ........................................................................................6 Diels-Alder Reactions .......................................................................6 Hydrogenation Reactions ..................................................................7 Friedel-Crafts Reactions ...................................................................8 Grignard Reactions ...........................................................................8 Electrolytes for Batteries ...................................................................9 Synthesis of 1-alkyl-3-methylimidazolium Based Ionic Liquids ................10 Properties of 1-alkyl-3-methylimidazolium Based Ionic Liquids ...............12 Thermal Properties ...........................................................................12 Density and Viscosity ......................................................................13 Solvent Miscibility ...........................................................................15 Electrochemical Properties ..............................................................16 Electrochemical Cells ..................................................................................18 iv Primary Cells ...................................................................................19 Secondary Cells ...............................................................................20 Lead-Acid Batteries ............................................................20 Nickel-Cadmium Batteries ...................................................21 Lithium and Lithium Ion Batteries ......................................22 Ionic Liquids in Lithium and Lithium Ion Batteries ........................25 II. Experimental .......................................................................................................27 Materials ......................................................................................................27 Instrumentation and Characterization ..........................................................27 Fourier-Transform Nuclear Magnetic Resonance ...........................27 Absorption and Desorption of Water ...............................................28 Fourier-Transform Infrared Spectroscopy .......................................28 Density .............................................................................................28 Viscosity ..........................................................................................29 Thermal Gravimetric Analysis .........................................................30 Conductivity .....................................................................................31 Electrochemical Properties ..............................................................32 Synthesis ......................................................................................................33 Preparation of 1-ethyl-3-methylimidazolium chloride ....................33 Preparation of 1-ethyl-3-methylimidazoium bis(pentafluoroethylsulfonyl)imide ......................................34 Preparation of 1-propyl-3-methylimidazolium chloride ..................34 v Preparation of 1-propyl-3-methylimidazoium bis(pentafluoroethylsulfonyl)imide ......................................35 Preparation of 1-butyl-3-methylimidazolium chloride ....................35 Preparation of 1-butyl-3-methylimidazoium bis(pentafluoroethylsulfonyl)imide ......................................36 Preparation of 1-pentyl-3-methylimidazolium chloride ..................36 Preparation of 1-butyl-3-methylimidazoium bis(pentafluoroethylsulfonyl)imide ......................................36 Preparation of 1-hexyl-3-methylimidazolium chloride ...................36 Preparation of 1-butyl-3-methylimidazoium bis(pentafluoroethylsulfonyl)imide ......................................37 III. Results and Discussion ......................................................................................38 Absorption and Desorption of Water ...........................................................39 Water Absorption Studies by Infrared Spectroscopy...................................47 Density .........................................................................................................52 Viscosity ......................................................................................................53 Thermal Properties of the Ionic Liquids ......................................................55 Conductivity .................................................................................................57 Electrochemical Properties ..........................................................................66 IV. Conclusion .........................................................................................................68 V. References ...........................................................................................................70 VI. Appendix............................................................................................................75 vi LIST OF FIGURES Figure Page 1. Common cations and anions used in the formation of ionic liquids .....................5 2. The reaction of isoprene and but-3-en-2-one catalyzed by ZnI2 using BMIPF6 as the solvent .................................................................................................6 3. The acylation of ferrocene using an N-ethyl-N’-methylimidazolium iodide/halogenaluminate ionic liquid as both the solvent and the catalyst ...8 4. Use of a novel ionic
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