Thermophysical properties and proton transport mechanisms of trialkylammonium and 1-alkyl-1H-imidazol-3-ium protic ionic liquids

Industrial and Engineering Chemistry Research

Volumn 51, Issue 43, 2012, Pages 14084-14098

  Lebga Nebane, Janice L ^a   Rock, Simon E ^b   Franclemont, Joshua ^a   Roy, Dipankar ^b   Krishnan, Sitaraman ^a  

^a Clarkson University   (United States)

^b CLARKSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE DELOCALIZATION; ELECTROCHEMICAL STABILITIES; GROTTHUSS MECHANISM; HYDROGEN BONDING INTERACTIONS; IMIDAZOLIUM; PROTON TRANSPORT; ROOM TEMPERATURE; STRUCTURE PROPERTY RELATION; THERMOPHYSICAL; TRANSITION BEHAVIOR; TRIFLATES; VAN DER WAALS INTERACTIONS;

AMMONIUM COMPOUNDS; DIFFUSION; HYDROGEN BONDS; IONIC CONDUCTIVITY; IONIC LIQUIDS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; VAN DER WAALS FORCES; VISCOSITY;

THERMODYNAMIC PROPERTIES;

EID: 84869056341     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie301687c     Document Type: Article

References (57)

1. Larminie, J.; Dicks, A. Proton Exchange Membrane Fuel Cells. In Fuel Cell Systems Explained; John Wiley & Sons: Chichester, England, 2003.
2. Yang, C.; Costamagna, P.; Srinivasan, S.; Benziger, J.; Bocarsly, A. B. Approaches and Technical Challenges to High Temperature Operation of Proton Exchange Membrane Fuel Cells J. Power Sources 2001, 103 (1) 1-9 (Pubitemid 33094096)
3. Yang, C.; Srinivasan, S.; Bocarsly, A. B.; Tulyani, S.; Benziger, J. B. A Comparison of Physical Properties and Fuel Cell Performance of Nafion and Zirconium Phosphate/Nafion Composite Membranes J. Membr. Sci. 2004, 237 (1-2) 145-161 (Pubitemid 38638362)
4. Lee, S.-Y.; Ogawa, A.; Kanno, M.; Nakamoto, H.; Yasuda, T.; Watanabe, M. Nonhumidified Intermediate Temperature Fuel Cells Using Protic Ionic Liquids J. Am. Chem. Soc. 2010, 132 (28) 9764-9773
5. Iojoiu, C.; Judeinstein, P.; Sanchez, J.-Y. Ion Transport in CLIP: Investigation through Conductivity and NMR Measurements Electrochim. Acta 2007, 53 (4) 1395-1403 (Pubitemid 350011179)
6. Doyle, M.; Choi, S. K.; Proulx, G. High-Temperature Proton Conducting Membranes Based on Perfluorinated Ionomer Membrane-Ionic Liquid Composites J. Electrochem. Soc. 2000, 147 (1) 34-37 (Pubitemid 30551883)
7. Lee, S.-Y.; Quan, D. N.; Hwang, M. J.; Lee, D. S.; Kim, H.; Lee, H.; Kim, S. H. Polymer Electrolyte Membranes for Fuel Cells J. Ind. Eng. Chem. 2006, 12 (2) 175-183 (Pubitemid 43480718)
8. Angell, C. A.; Xu, W.; Yoshizawa-Fujita, M.; Hayashi, A.; Belieres, J.-P.; Lucas., P.; Videa, M.; Zhao, Z.-F.; Ueno, K.; Ansari, Y.; Thomson, J.; Gervasio, D. Physical Chemistry of Ionic Liquids: Inorganic and Organic as Well as Protic and Aprotic. In Electrochemical Aspects of Ionic Liquids, 2 nd ed.; Ohno, H., Ed.; John Wiley & Sons: Hoboken, NJ, 2011; pp 5-31.
9. Angell, C. A.; Byrne, N.; Belieres, J.-P. Parallel Developments in Aprotic and Protic Ionic Liquids: Physical Chemistry and Applications Acc. Chem. Res. 2007, 40 (11) 1228-1236
10. Freemantle, M. Introduction. In Introduction to Ionic Liquids, The Royal Society of Chemistry: Cambridge, UK, 2010; pp 1-11.
11. Ohno, H.; Yoshizawa, M. Ion Conductive Characteristics of Ionic Liquids Prepared by Neutralization of Alkylimidazoles Solid State Ionics 2002, 154-155, 303-309 (Pubitemid 35458932)
12. Nakamoto, H.; Noda, A.; Hayamizu, K.; Hayashi, S.; Hamaguchi, H.-o.; Watanabe, M. Proton-Conducting Properties of a Brønsted Acid-Base Ionic Liquid and Ionic Melts Consisting of Bis(trifluoromethanesulfonyl)imide and Benzimidazole for Fuel Cell Electrolytes J. Phys. Chem. C 2007, 111 (3) 1541-1548 (Pubitemid 46347104)
13. Nakamoto, H.; Watanabe, M. Brønsted Acid-Base Ionic Liquids for Fuel Cell Electrolytes Chem. Commun. 2007, 24, 2539-2541 (Pubitemid 46906702)
14. Susan, M. A. B. H.; Noda, A.; Mitsushima, S.; Watanabe, M. Brønsted Acid-Base Ionic Liquids and Their Use as New Materials for Anhydrous Proton Conductors Chem. Commun. 2003, 8, 938-939 (Pubitemid 36469638)
15. Noda, A.; Susan, M. A. B. H.; Kudo, K.; Mitsushima, S.; Hayamizu, K.; Watanabe, M. Brønsted Acid-Base Ionic Liquids as Proton-Conducting Nonaqueous Electrolytes J. Phys. Chem. B 2003, 107 (17) 4024-4033
16. Iojoiu, C.; Martinez, M.; Hanna, M.; Molmeret, Y.; Cointeaux, L.; Leprêtre, J.-C.; Kissi, N. E.; Guindet, J.; Judeinstein, P.; Sanchez, J.-Y. PILS-Based Nafion Membranes: A Route to High-Temperature PEMFCs Dedicated to Electric and Hybrid Vehicles Polym. Adv. Technol. 2008, 19 (10) 1406-1414
17. Judeinstein, P.; Iojoiu, C.; Sanchez, J.-Y.; Ancian, B. Proton Conducting Ionic Liquid Organization as Probed by NMR: Self-Diffusion Coefficients and Heteronuclear Correlations J. Phys. Chem. B 2008, 112 (12) 3680-3683
18. Blanchard, J. W.; Belières, J.-P.; Alam, T. M.; Yarger, J. L.; Holland, G. P. NMR Determination of the Diffusion Mechanisms in Triethylamine-Based Protic Ionic Liquids J. Phys. Chem. Lett. 2011, 2 (9) 1077-1081
19. Ogihara, W.; Kosukegawa, H.; Ohno, H. Proton-Conducting Ionic Liquids Based Upon Multivalent Anions and Alkylimidazolium Cations Chem. Commun. 2006, 34, 3637-3639 (Pubitemid 44267652)
20. Martinez, M.; Molmeret, Y.; Cointeaux, L.; Iojoiu, C.; Leprêtre, J.-C.; El Kissi, N.; Judeinstein, P.; Sanchez, J.-Y. Proton-Conducting Ionic Liquid-Based Proton Exchange Membrane Fuel Cell Membranes: The Key Role of Ionomer-Ionic Liquid Interaction J. Power Sources 2010, 195 (18) 5829-5839
21. Lin, B.; Cheng, S.; Qiu, L.; Yan, F.; Shang, S.; Lu, J. Protic Ionic Liquid-Based Hybrid Proton-Conducting Membranes for Anhydrous Proton Exchange Membrane Application Chem. Mater. 2010, 22 (5) 1807-1813
22. Sekhon, S. S.; Lalia, B. S.; Park, J.-S.; Kim, C.-S.; Yamada, K. Physicochemical Properties of Proton Conducting Membranes Based on Ionic Liquid Impregnated Polymer for Fuel Cells J. Mater. Chem. 2006, 16 (23) 2256-2265 (Pubitemid 43876342)
23. Schauer, J.; Sikora, A.; Plíšková, M.; Mališ, J.; Mazúr, P.; Paidar, M.; Bouzek, K. Ion-Conductive Polymer Membranes Containing 1-Butyl-3-Methylimidazolium Trifluoromethanesulfonate and 1-Ethylimidazolium Trifluoromethanesulfonate J. Membr. Sci. 2011, 367 (1-2) 332-339
24. Fernicola, A.; Panero, S.; Scrosati, B.; Tamada, M.; Ohno, H. New Types of Brönsted Acid-Base Ionic Liquids-Based Membranes for Applications in PEMFCs ChemPhysChem 2007, 8 (7) 1103-1107
25. Xu, A.; Wang, J.; Zhang, Y.; Chen, Q. Effect of Alkyl Chain Length in Anions on Thermodynamic and Surface Properties of 1-Butyl-3-methylimidazolium Carboxylate Ionic Liquids Ind. Eng. Chem. Res. 2012, 51 (8) 3458-3465
26. Timperman, L.; Anouti, M. Transport Properties of Tributylphosphonium Tetrafluoroborate Protic Ionic Liquid Ind. Eng. Chem. Res. 2012, 51 (7) 3170-3178
27. Gasteiger, J.; Marsili, M. Iterative Partial Equalization of Orbital Electronegativity-A Rapid Access to Atomic Charges Tetrahedron 1980, 36 (22) 3219-3228
28. Yaws, C. L.; Narasimhan, P. K.; Gabbula, C. Yaws' Handbook of Antoine Coefficients for Vapor Pressure, 2 nd electronic ed. [Online]; Knovel: New York, NY, 2009. http://www.knovel.com/web/portal/browse/display?-EXT-KNOVEL-DISPLAY- bookid=1183&VerticalID=0 (accessed June 1, 2012).
29. Belieres, J.-P.; Angell, C. A. Protic Ionic Liquids: Preparation, Characterization, and Proton Free Energy Level Representation J. Phys. Chem. B 2007, 111 (18) 4926-4937 (Pubitemid 46826403)
30. Crosthwaite, J. M.; Muldoon, M. J.; Dixon, J. K.; Anderson, J. L.; Brennecke, J. F. Phase Transition and Decomposition Temperatures, Heat Capacities and Viscosities of Pyridinium Ionic Liquids J. Chem. Thermodyn. 2005, 37 (6) 559-568 (Pubitemid 40750633)
31. Pringle, J. M.; Golding, J.; Baranyai, K.; Forsyth, C. M.; Deacon, G. B.; Scott, J. L.; MacFarlane, D. R. The Effect of Anion Fluorination in Ionic Liquids-Physical Properties of a Range of Bis(methanesulfonyl)amide Salts New J. Chem. 2003, 27 (10) 1504-1510 (Pubitemid 37290008)
32. Dong, K.; Zhang, S. Hydrogen Bonds: A Structural Insight into Ionic Liquids Chem.-Eur. J. 2012, 18 (10) 2748-2761
33. Ueno, K.; Zhao, Z.; Watanabe, M.; Angell, C. A. Protic Ionic Liquids Based on Decahydroisoquinoline: Lost Superfragility and Ionicity-Fragility Correlation J. Phys. Chem. B 2011, 116 (1) 63-70
34. Thorsmølle, V. K.; Brauer, J. C.; Zakeeruddin, S. M.; Grätzel, M.; Moser, J.-E. Temperature-Dependent Ordering Phenomena of a Polyiodide System in a Redox-Active Ionic Liquid J. Phys. Chem. C 2012, 116 (14) 7989-7992
35. Ganapatibhotla, L. V. N. R.; Zheng, J.; Roy, D.; Krishnan, S. PEGylated Imidazolium Ionic Liquid Electrolytes: Thermophysical and Electrochemical Properties Chem. Mater. 2010, 22 (23) 6347-6360
36. Galiński, M.; Lewandowski, A.; Stȩpniak, I. Ionic Liquids as Electrolytes Electrochim. Acta 2006, 51 (26) 5567-5580 (Pubitemid 44148550)
37. Yoshizawa-Fujita, M.; Ohno, H. Fuel Cells. In Electrochemical Aspects of Ionic Liquids, 2 nd ed.; Ohno, H., Ed.; John Wiley & Sons: Hoboken, NJ, 2011; pp 235-242.
38. Angell, C. A. Formation of Glasses from Liquids and Biopolymers Science 1995, 267 (5206) 1924-1935
39. Harris, K. R.; Kanakubo, M.; Woolf, L. A. Temperature and Pressure Dependence of the Viscosity of the Ionic Liquids 1-Hexyl-3-methylimidazolium Hexafluorophosphate and 1-Butyl-3-methylimidazolium Bis(trifluoromethylsulfonyl) imide J. Chem. Eng. Data 2007, 52 (3) 1080-1085 (Pubitemid 46848280)
40. Hodge, I. M. Strong and Fragile Liquids-A Brief Critique J. Non-Cryst. Solids 1996, 202 (1-2) 164-172 (Pubitemid 126363557)
41. Barrat, J.-L.; Hansen, J.-P. Slow Relaxations. In Basic Concepts for Simple and Complex Liquids; Cambridge University Press: Cambridge, UK, 2003; pp 273-293.
42. Shamim, N.; McKenna, G. B. Glass Dynamics and Anomalous Aging in a Family of Ionic Liquids Above the Glass Transition Temperature J. Phys. Chem. B 2010, 114 (48) 15742-15752
43. Ganapatibhotla, L. V. N. R.; Wu, L.; Zheng, J.; Jia, X.; Roy, D.; McLaughlin, J. B.; Krishnan, S. Ionic Liquids with Fluorinated Block-Oligomer Tails: Influence of Self-Assembly on Transport Properties J. Mater. Chem. 2011, 21 (48) 19275-19285
44. Schreiner, C.; Zugmann, S.; Hartl, R.; Gores, H. J. Fractional Walden Rule for Ionic Liquids: Examples from Recent Measurements and a Critique of the So-Called Ideal KCl Line for the Walden Plot J. Chem. Eng. Data 2009, 55 (5) 1784-1788
45. Xu, W.; Cooper, E. I.; Angell, C. A. Ionic Liquids: Ion Mobilities, Glass Temperatures, and Fragilities J. Phys. Chem. B 2003, 107 (25) 6170-6178
46. Dissociation Constants of Organic Acids and Bases. In CRC Handbook of Chemistry and Physics, 92 nd ed. [Online]; Haynes, W. M., Ed.; CRC Press/Taylor and Francis: Boca Raton, FL, 2012. http://hbcpnetbase.com/ (accessed June 1, 2012).
47. Lenarcik, B.; Ojczenasz, P. The Influence of the Size and Position of the Alkyl Groups in Alkylimidazole Molecules on Their Acid-Base Properties J. Heterocycl. Chem. 2002, 39 (2) 287-290 (Pubitemid 34526060)
48. a Holding over a Range of 20 p K Units Can. J. Chem. 1978, 56 (17) 2342-2354
49. Tanner, J. E. Use of the Stimulated Echo in NMR Diffusion Studies J. Chem. Phys. 1970, 52 (5) 2523-2526
50. Burstein, D. Stimulated Echoes: Description, Applications, Practical Hints Concepts Magn. Reson. 1996, 8 (4) 269-278
51. Price, W. S. Pulsed-Field Gradient Nuclear Magnetic Resonance as a Tool for Studying Translational Diffusion: Part 1. Basic Theory Concepts Magn. Reson. 1997, 9 (5) 299-336 (Pubitemid 127116750)
52. 19F NMR Ionic Diffusion Coefficient, Viscosity, and Ionic Conductivity of Non-Chloroaluminate Room-Temperature Ionic Liquids J. Phys. Chem. B 2001, 105 (20) 4603-4610 (Pubitemid 35372684)
53. Wilkes, J. S.; Zaworotko, M. J. Manifestations of Noncovalent Interactions in the Solid State. Dimeric and Polymeric Self-Assembly in Imidazolium Salts Via Face-to-Face Cation-Cation π-π Stacking Supramol. Chem. 1993, 1 (3-4) 191-193
54. Li, H.; Boatz, J. A.; Gordon, M. S. Cation-Cation π-π Stacking in Small Ionic Clusters of 1,2,4-Triazolium J. Am. Chem. Soc. 2007, 130 (2) 392-393
55. Li, J. C. M.; Chang, P. Self-Diffusion Coefficient and Viscosity in Liquids J. Chem. Phys. 1955, 23 (3) 518-520
56. Nomura, H.; Ohba, M. Effects of Molecular Conformation on the Packing Density in the Liquid State J. Phys. Chem. 1989, 93 (24) 8101-8104
57. Stolwijk, N. A.; Obeidi, S. Combined Analysis of Self-Diffusion, Conductivity, and Viscosity Data on Room Temperature Ionic Liquids Electrochim. Acta 2009, 54 (5) 1645-1653