Transport properties of tributylphosphonium tetrafluoroborate protic ionic liquid

Industrial and Engineering Chemistry Research

Volumn 51, Issue 7, 2012, Pages 3170-3178

  Timperman, Laure ^a   Anouti, Mériem ^a  

^a UNIVERSITÉ DE TOURS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DOMINATING FACTORS; ELECTROCHEMICAL DEVICES; INFINITE DILUTION; MOLAR CONDUCTIVITIES; NEGATIVE DEVIATIONS; NEWTONIAN BEHAVIOR; TEMPERATURE DEPENDENCE; TETRAFLUOROBORATES; VISCOSITY DEVIATIONS; VISCOSITY PARAMETERS;

ACETONITRILE; ELECTROLYTES; IONIC LIQUIDS;

TRANSPORT PROPERTIES;

EID: 84857397949     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie202412u     Document Type: Article

References (57)

1. Earle, M. J.; Seddon, K. R. Ionic liquids. Green solvents for the future Pure Appl. Chem. 2000, 72, 1391
2. Plechkova, N. V.; Seddon, K. R. Applications of ionic liquids in the chemical industry Chem. Soc. Rev. 2008, 37, 123
3. Wasserscheid, P.; Keim, W. Ionic liquids-new ″solutions″ for transition metal catalysis Angew. Chem., Int. Ed. 2000, 39, 3772
4. Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem. Rev. 1999, 99, 2071
5. Minami, I. Ionic Liquids in Tribology Molecule. 2009, 14, 2286
6. Reich, R. A.; Atewart, P. A.; Bohaychick, J.; Urbansky, J. A. Base Oil Properties of Ionic Liquids Lubr. Eng. 2003, 59, 16
7. Ye, C.; Liu, W.; Chen, Y.; Yu, L. Room-temperature ionic liquids: a novel versatile lubricant Chem. Commun. 2001, 2244
8. Hough, W. L.; Rogers, R. D. Ionic liquids then and now: From solvents to materials to active pharmaceutical ingredients Bull. Chem. Soc. Jpn. 2007, 80, 2262
9. Hough, W. L.; Smiglak, M.; Rodriguez, H.; Swatloski, R. P.; Spear, S. K.; Daly, D. T.; Pernak, J.; Grisel, J. E.; Carliss, R. D.; Soutullo, M. D.; Davis, J. J. H.; Rogers, R. D. The third evolution of ionic liquids: active pharmaceutical ingredients New J. Chem. 2007, 31, 1429
10. MacFarlane, D. R.; Forsyth, M.; Howlett, P. C.; Pringle, J. M.; Sun, J.; Annat, G.; Neil, W.; Izgorodina, E. I. Ionic Liquids in Electrochemical Devices and Processes: Managing Interfacial Electrochemistry Acc. Chem. Res. 2007, 40, 1165
11. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Ionic Liquid (Molten Salt) Phase organometallic. Catalysis Chem. Rev. 2002, 102, 3667
12. Araos, M. U.; Warr, G. G. Structure of Nonionic Surfactant Micelles in Ethylammonium Nitrate Langmuir 2008, 24, 9354
13. Blanchard, L. A.; Hancu, D.; Beckman, E. J.; Brennecke, J. F. Green processing using ionic liquids and CO2 Nature 1999, 399, 28
14. Eastoe, J.; Gold, S.; Rogers, S. E.; Paul, A.; Welton, T.; Heenan, R. K.; Grillo, I. Ionic liquid-in-oil microemulsions J. Am. Chem. Soc. 2005, 127, 7302
15. Hagiwara, R.; Ito, Y. Room temperature ionic liquids of alkylimidazolium cations and fluoroanions J. Fluorine Chem. 2000, 105, 221
16. He, Y.; Li, Z.; Simone, P.; Lodge, T. P. Self-Assembly of Block Copolymer Micelles in an Ionic Liquid J. Am. Chem. Soc. 2006, 128, 2745
17. Kim, K. S.; Choi, S.; Demberelnyamba, D.; Lee, H.; Oh, J.; Lee, B. B.; Mun, S. J. Ionic liquids based on N-alkyl-Nmethylmorpholinium salts as potential electrolytes Chem. Commun. 2004, 828
18. Greaves, T. L.; Drummond., C. J. Protic ionic liquids: Properties and applications Chem. Rev. 2008, 108, 206
19. Greaves, T. L.; Weerawardena, A.; Fong, C.; Krodkiewska, I.; Drummond., C. J. Protic Ionic Liquids: Solvents with Tunable Phase Behavior and Physicochemical Properties J. Phys. Chem. B. 2006, 110, 22479
20. Xu, W.; Angell, C. A. Solvent-Free Electrolytes with Aqueous Solution-Like Conductivities Science 2003, 302, 422
21. Yoshizawa, M.; Xu, W.; Angell., C. A. Ionic Liquids by Proton Transfer: Vapor Pressure, Conductivity, and the Relevance of ΔpKa from Aqueous Solutions J. Am. Chem. Soc. 2003, 125, 15411
22. Bradaric, C. J.; Downard, A.; Kennedy, C.; Robertson, A. J.; Zhou., Y. Industrial. Preparation of Phosphonium Ionic Liquids Green Chem. 2003, 5, 143
23. Fraser, K. J.; MacFarlane., D. R. Phosphonium-Based Ionic Liquids: An Overview Aust. J. Chem. 2009, 62, 309
24. Tsunashima, K.; Sugiya, M. Physical and electrochemical properties of low-viscosity phosphonium ionic liquids as potential electrolytes Electrochem. Commun. 2007, 9, 2353
25. Tsunashima, K.; Sugiya, M. Physical and electrochemical properties of room temperature ionic liquids based on quaternary phosphonium cations Electrochemistry 2007, 75, 734
26. Duffy, N. W.; Bond., A. M. Macroelectrode Voltammetry in Toluene using a Phosphonium-Phosphate Ionic Liquid as the Supporting Electrolyte Electrochem. Commun. 2006, 8, 892
27. Ramírez, R. E.; Sánchez, E. M. Molten phosphonium iodides as electrolytes in Dye-. Sensitized Nanocrystalline Sol. Energy Mater. Sol. Cells. 2006, 90, 2384
28. Frackowiak, E.; Lota, G.; Pernak, J. Room-temperature phosphonium ionic liquids for supercapacitor Appl. Phys. Lett. 2005, 86, 164104
29. Ramirez, R. E.; Torres-Gonzalez, L. C.; Sanchez, E. M. Electrochemical aspects of assymetric phosphonium ionic liquids J. Electrochem. Soc. 2007, 154, B229
30. Picquet, M.; Stutzmann, S.; Tkatchenko, I.; Tommasi, I.; Zimmermann, J.; Wasserscheid, P. Selective palladium-catalysed dimerisation of methyl acrylate in ionic liquids: towards a continuous process Green Chem. 2003, 5, 153
31. Zimmermann, J.; Wasserscheid, P.; Tkatchenko, I.; Stutzmann, S. Biphasic dimerisation of methylacrylate-Immobilisation and stabilisation of cationic Pd-catalysts in ionic liquids by an ammoniumphosphine ligand Chem. Commun. 2002, 760
32. Thansandote, P.; Hulcoop, D. G.; Langer, M.; Lautens, M. Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles J. Org. Chem. 2009, 74, 1673
33. Lautens, M.; Paquin, J.-F. Diastereoselective palladium-catalyzed formate reduction of allylic carbonates as a new entry into propionate units Org. Lett. 2003, 5, 3391
34. Klapars, A.; Campos, K. R.; Waldman, J. H.; Zewge, D.; Dormer, P. G.; Chen, C.-y. Enantioselective Pd-Catalyzed r-Arylation of N-Boc-Pyrrolidine: The Key to an Efficient and Practical Synthesis of a Glucokinase Activator J. Org. Chem. 2008, 73, 4986
35. Tsukamoto, H.; Ueno, T.; Kondo, Y. Palladium(0)-Catalyzed Alkylative Cyclization of Alkynals and Alkynones: Remarkable trans-Addition of Organoboronic Reagents J. Am. Chem. Soc. 2006, 128, 1406
36. Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. A convergent synthesis of polysubstituted aromatic nitriles via palladium-catalyzed C-H functionalization J. Am. Chem. Soc. 2007, 129, 15372
37. Gooßen, L. J.; Arndt, M.; Blanchot, M.; Rudolphi, F.; Menges, F.; Niedner-Schatteburg, G. A Practical and Effective Ruthenium Trichloride-Based Protocol for the Regio- and Stereoselective Catalytic Hydroamidation of Terminal Alkynes Adv. Synth. Catal. 2008, 350, 2701
38. Timperman, L.; Galiano, H.; Lemordant, D.; Anouti, M. Phosphonium-based protic ionic liquid as electrolyte for carbon-based supercapacitors Electrochem. Commun. 2011, 10, 1112
39. Greaves, T. L.; Weerawardena, A.; Krodkiewska, I.; Drummond, C. J. Protic Ionic Liquids: Physicochemical Properties and Behavior as Amphiphile Self-Assembly Solvents J. Phys. Chem. B 2008, 112, 896
40. Galinski, M.; Lewandowski, A.; Stepniak, I. Ionic liquids as electrolytes Electrochim. Acta 2006, 51, 5567
41. Tsunashima, K.; Yonekawa, F.; Kikuchi, M.; Sugiya, M. Tributylmethylphosphonium Bis(trifluoromethylsulfonyl)amide as an Effective Electrolyte Additive for Lithium Secondary Batteries J. Electrochem. Soc. 2010, 157, A1274
42. Tsunashima, K.; Niwa, E.; Kodama, S.; Sugiya, M.; Ono, Y. Thermal and Transport Properties of Ionic Liquids Based on Benzyl-Substituted Phosphonium Cations J. Phys. Chem. B 2009, 113, 15870
43. Tsunashima, K.; Ono, Y.; Sugiya, M. Physical and electrochemical characterization of ionic liquids based on quaternary phosphonium cations containing a carbon-carbon double bon Electrochim. Acta 2011, 11, 4351
44. Tsunashima, K.; Kawabata, A.; Matsumiya, M.; Kodama, S.; Enomoto, R.; Sugiya, M.; Kunugi, Y. Low viscous and highly conductive phosphonium ionic liquids based on bis(fluorosulfonyl)amide anion as potential electrolytes Electrochem. Commun. 2011, 13, 178
45. Kanematsu, S.; Matsumoto, K.; Hagiwara, R. Electrochemically stable fluorohydrogenate ionic liquids based on quaternary phosphonium cations Electrochem. Commun. 2009, 11, 1312
46. Tsunashima, K.; Kodama, S.; Sugiya, M.; Kunugi, Y. Physical and electrochemical properties of room-temperature dicyanamide ionic liquids based on quaternary phosphonium cations Electrochim. Acta 2010, 56, 762
47. Burrell, G. L.; Dunlop, N. F.; Separovic, F. Non-Newtonian viscous shear thinning in ionic liquids Soft Matter 2010, 6, 2080
48. Okoturo, O. O.; VanderNoot, T. J. Temperature dependence of viscosity for room temperature ionic liquids J. Electroanal. Chem. 2004, 568, 167
49. McFarlane, D. R.; Sun, J.; Golding, J.; Meakin, P.; Forsyth, M. High conductivity molten salts based on the imide ion Electrochim. Acta 2000, 45, 1271
50. Tao, G.-h.; He, L.; Sun, N.; Kou, Y. New Generation Ionic Liquids: Cations Derived from Amino Acids Chem. Commun. 2005, 3562
51. Matsumiya, M.; Suda, S.; Tsunashima, K.; Sugiya, M.; Kishioka, S.-y.; Matsuura, H. Electrochemical behaviors of multivalent complexes in room temperature ionic liquids based on quaternary phosphonium cations J. Electroanal. Chem. 2008, 622, 129
52. Anouti, M.; Caillon-Caravanier, M.; Le Floch, C.; Lemordant, D. Alkylammonium-based protic ionic liquids. II. Ionic transport and heat-transfer properties: Fragility and ionicity rule J. Phys. Chem. B. 2008, 112, 9412
53. Varela, L. M.; Carrete, J.; Garcia, M.; Gallego, L. J.; Turmine, M.; Rilo, E.; Cabeza, O. Pseudolattice theory of charge transport in ionic solutions: Corresponding states law for the electric conductivity Fluid Phase Equilib. 2010, 298, 280
54. Robinson, R. A.; Stokes, R. H. Electrolyte solutions: the measurement and interpretation of conductance, chemical potential and diffusion in solutions of simple electrolytes; Butterworths: London, U.K., 1965.
55. Barthel, J.; Krienke, H.; Kunz, W. Physical Chemistry of Electrolyte Solutions. In Topics in Physical Chemistry; Steinkopff: Darmstadt, Germany and Springer: New York, 1998.
56. Anouti, M.; Vigeant, A.; Jacquemin, J.; Brigouleix, C.; Lemordant, D. Volumetric properties, viscosity and refractive index of the protic ionic liquid, pyrrolidinium octanoate, in molecular solvents J. Chem. Thermodyn. 2010, 42, 834
57. Leys, J.; Rajesh, N. R.; Menon, C. P.; Glorieux, C.; Longuemart, S.; Nockemann, P.; Pellens, M.; Binnemans, K. Influence of the anion on the electrical conductivity and glass formation of 1-butyl-3-methylimidazolium ionic liquids J. Chem. Phys. 2010, 133, 034503