Cation alkyl side chain length and symmetry effects on the surface tension of ionic liquids

Langmuir

Volumn 30, Issue 22, 2014, Pages 6408-6418

  Almeida, Hugo F D ^a   Freire, Mara G ^a   Fernandes, Ana M ^b   Lopes Da Silva, José A ^b   Morgado, Pedro ^c   Shimizu, Karina ^c   Filipe, Eduardo J M ^c   Canongia Lopes, José N ^c,d   Santos, Luís M N B F ^e   Coutinho, João A P ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^d INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^e UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

CHAIN LENGTH; IONIC LIQUIDS; MOLECULAR DYNAMICS; POSITIVE IONS;

ALKYL CHAIN LENGTHS; ALKYL SIDE-CHAIN LENGTHS; CRITICAL TEMPERATURES; DIALKYLIMIDAZOLIUM; LONG CHAIN N-ALKANES; MOLECULAR DYNAMICS SIMULATIONS; STRUCTURAL ORGANIZATION; SURFACE ORGANIZATION;

SURFACE TENSION;

EID: 84902148809     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la501308q     Document Type: Article

References (52)

1. Seddon, K. R. Ionic liquids: A taste of the future Nat. Mater. 2003, 2, 363-365
2. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2084
3. Gaune-Escard, M.; Seddon, K. R.: Molten salts and ionic liquids: never the twain? John Wiley: Hoboken, N.J., 2010.
4. Rogers, R. D.; Seddon, K. R. Ionic Liquids-Solvents of the Future? Science 2003, 302, 792-793
5. Conceição, L. J. A.; Bogel-Lukasik, E.; Bogel-Lukasik, R. A new outlook on solubility of carbohydrates and sugar alcohols in ionic liquids RSC Adv. 2012, 2, 1846-1855
6. Wang, H.; Gurau, G.; Rogers, R. D. Ionic liquid processing of cellulose Chem. Soc. Rev. 2012, 41, 1519-1537
7. Plechkova, N. V.; Seddon, K. R. Applications of ionic liquids in the chemical industry Chem. Soc. Rev. 2008, 37, 123-150
8. Kolbeck, C.; Lehmann, J.; Lovelock, K. R. J.; Cremer, T.; Paape, N.; Wasserscheid, P.; Fröba, A. P.; Maier, F.; Steinrück, H. P. Density and Surface Tension of Ionic Liquids J. Phys. Chem. B 2010, 114, 17025-17036
9. Law, G.; Watson, P. R. Surface Tension Measurements of N-Alkylimidazolium Ionic Liquids Langmuir 2001, 17, 6138-6141
10. Tariq, M.; Freire, M. G.; Saramago, B.; Coutinho, J. A. P.; Lopes, J. N. C.; Rebelo, L. P. N. Surface tension of ionic liquids and ionic liquid solutions Chem. Soc. Rev. 2012, 41, 829-868
11. 2-Based Ionic Liquids: Pure and Water-Saturated Mixtures J. Chem. Eng. Data 2010, 55, 4514-4520
12. Freire, M. G.; Neves, C. M. S. S.; Shimizu, K.; Bernardes, C. E. S.; Marrucho, I. M.; Coutinho, J. A. P.; Lopes, J. N. C.; Rebelo, L. P. N. Mutual Solubility of Water and Structural/Positional Isomers of N-Alkylpyridinium-Based Ionic Liquids J. Phys. Chem. B 2010, 114, 15925-15934
13. Rocha, M. A. A.; Neves, C. M. S. S.; Freire, M. G.; Russina, O.; Triolo, A.; Coutinho, J. A. P.; Santos, L. M. N. B. F. Alkylimidazolium Based Ionic Liquids: Impact of Cation Symmetry on Their Nanoscale Structural Organization J. Phys. Chem. B 2013, 117, 10889-10897
14. Almeida, H. F. D.; Lopes-da-Silva, J. A.; Freire, M. G.; Coutinho, J. A. P. Surface tension and refractive index of pure and water-saturated tetradecyltrihexylphosphonium-based ionic liquids J. Chem. Thermodyn. 2013, 57, 372-379
15. Fernandes, A. M.; Rocha, M. A. A.; Freire, M. G.; Marrucho, I. M.; Coutinho, J. A. P.; Santos, L. M. N. B. F. Evaluation of Cation-Anion Interaction Strength in Ionic Liquids J. Phys. Chem. B 2011, 115, 4033-4041
16. Canongia Lopes, J. N.; Deschamps, J.; Pádua, A. A. H. Modeling ionic liquids using a systematic all-atom force field J. Phys. Chem. B 2004, 108, 2038-2047
17. Canongia Lopes, J. N.; Pádua, A. A. H. Molecular Force Field for Ionic Liquids Composed of Triflate or Bistriflylimide Anions J. Phys. Chem. B 2004, 108, 16893-16898
18. Smith, W.; Forester, T. R. The DL-POLY Package of Molecular Simulation Routines (v.2.2); The Council for The Central Laboratory of Research Councils; Daresbury Laboratory: Warrington, U.K., 2006.
19. Tariq, M.; Serro, A. P.; Mata, J. L.; Saramago, B.; Esperança, J. M. S. S.; Canongia Lopes, J. N.; Rebelo, L. P. N. High-temperature surface tension and density measurements of 1-alkyl-3-methylimidazolium bistriflamide ionic liquids Fluid Phase Equilib. 2010, 294, 131-138
20. Rebelo, L. P. N.; Canongia Lopes, J. N.; Esperança, J. M. S. S.; Filipe, E. On the Critical Temperature, Normal Boiling Point, and Vapor Pressure of Ionic Liquids J. Phys. Chem. B 2005, 109, 6040-6043
21. Carvalho, P. J.; Freire, M. G.; Marrucho, I. M.; Queimada, A. J.; Coutinho, J. A. P. Surface tensions for the 1-Alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquids J. Chem. Eng. Data 2008, 53, 1346-1350
22. Freire, M. G.; Carvalho, P. J.; Fernandes, A. M.; Marrucho, I. M.; Queimada, A. J.; Coutinho, J. A. P. Surface Tensions of Imidazolium Based Ionic Liquids: Anion, Cation, Temperature and Water Effect J. Colloid Interface Sci. 2007, 314, 621-630
23. Dzyuba, S. V.; Bartsch, R. A. Influence of Structural Variations in 1-Alkyl(aralkyl)-3-Methylimidazolium Hexafluorophosphates and Bis(trifluoromethylsulfonyl)imides on Physical Properties of the Ionic Liquids ChemPhysChem 2002, 3, 161-166
24. Law, G.; Watson, P. R. Surface orientation in ionic liquids Chem. Phys. Lett. 2001, 345, 1-4
25. Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. Structure and Properties of New Ionic Liquids Based on Alkyl- and Alkenyltrifluoroborates ChemPhysChem 2005, 6, 1324-1332
26. 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, 3458-3465
27. Pádua, A. A. H.; Costa Gomes, M. F.; Canongia Lopes, J. N. A. Molecular Solutes in Ionic Liquids: A Structural Perspective Acc. Chem. Res. 2007, 40, 1087-1096
28. Shimizu, K.; Bernardes, C. E. S.; Canongia Lopes, J. N. Structure and Aggregation in the 1-Alkyl-3-Methylimidazolium Bis(trifluoromethylsulfonyl)imide Ionic Liquid Homologous Series. J. Phys. Chem. B 2014, 118, 567-576
29. Santos, L. M. N. B. F.; Canongia Lopes, J. N.; Coutinho, J. A. P.; Esperança, J. M. S. S.; Gomes, L. R.; Marrucho, I. M.; Rebelo, L. P. N. Ionic Liquids: First Direct Determination of their Cohesive Energy J. Am. Chem. Soc. 2007, 129, 284-285
30. Olga, R.; Alessandro, T.; Lorenzo, G.; Ruggero, C.; Dong, X.; Larry, G. H., Jr.; Richard, A. B.; Edward, L. Q.; Natalia, P.; Kenneth, R. S. Morphology and intermolecular dynamics of 1-alkyl-3-methylimidazolium bis{(trifluoromethane)sulfonyl}amide ionic liquids: structural and dynamic evidence of nanoscale segregation J. Phys.: Condens. Matter 2009, 21, 424121
31. Lynden-Bell, R. M. Gas-liquid interfaces of room temperature ionic liquids Mol. Phys. 2003, 101, 2625-2633
32. Lynden-Bell, R. M.; Pópolo, M. G. D. Simulation of the surface structure of butylmethylimidazolium ionic liquids Phys. Chem. Chem. Phys. 2006, 8, 949-954
33. Pensado, A. S.; Malfreyt, P.; Pádua, A. H. A. Molecular Dynamics Simulations of the Liquid Surface of the Ionic Liquid 1-Hexyl-3- methylimidazolium Bis(trifluoromethanesulfonyl)amide: Structure and Surface Tension J. Phys. Chem. B 2009, 113, 14708-14718
34. Jiang, W.; Wang, Y.; Yan, T.; Voth, G. A. A Multiscale Coarse-Graining Study of the Liquid/Vacuum Interface of Room-Temperature Ionic Liquids with Alkyl Substituents of Different Lengths J. Phys. Chem. C 2008, 112, 1132-1139
35. Almeida, H. F. D.; Teles, A. R. R.; Lopes-da-Silva, J. A.; Freire, M. G.; Coutinho, J. A. P. Influence of the Anion on the Surface Tension of 1-ethyl-3-methylimidazolium-based Ionic Liquids J. Chem. Thermodyn. 2012, 54, 49-54
36. Langmuir, I. Forces Near the Surfaces of Molecules Chem. Rev. 1930, 6, 451-479
37. Adamson, A. W.; Gast, A. P. Physical Chemistry of Surfaces; John Wiley: New York, 1997.
38. Miller, J. C.; Miller, J. N. Statistics for Analytical Chemistry. PTR Prentice Hall: Chichester, U.K., 1993.
39. 2N J. Chem. Thermodyn. 2013, 65, 42-52
40. Bittner, B.; Wrobel, R. J.; Milchert, E. Physical properties of pyridinium ionic liquids J. Chem. Thermodyn. 2012, 55, 159-165
41. 4] (n = 2,3,4,5,6) J. Chem. Eng. Data 2012, 57, 2177-2184
42. Canongia Lopes, J. N. A.; Pádua, A. A. H. Using Spectroscopic Data on Imidazolium Cation Conformations To Test a Molecular Force Field for Ionic Liquids J. Phys. Chem. B 2006, 110, 7485-7489
43. Wang, X.; Vogel, C. S.; Heinemann, F. W.; Wasserscheid, P.; Meyer, K. Solid-State Structures of Double-Long-Chain Imidazolium Ionic Liquids: Influence of Anion Shape on Cation Geometry and Crystal Packing Cryst. Growth Des. 2011, 11, 1974-1988
44. Larriba, C.; Yoshida, Y.; Fernández de la Mora, J. Correlation between Surface Tension and Void Fraction in Ionic Liquids J. Phys. Chem. B 2008, 112, 12401-12407
45. Gardas, R. L.; Coutinho, J. A. P. Applying a QSPR correlation to the prediction of surface tensions of ionic liquids Fluid Phase Equilib. 2008, 265, 57-65
46. Gardas, R. L.; Freire, M. G.; Carvalho, P. J.; Marrucho, I. M.; Fonseca, I. M. A.; Ferreira, A. G. M.; Coutinho, J. A. P. P?T Measurements of Imidazolium-Based Ionic Liquids J. Chem. Eng. Data 2007, 52, 1881-1888
47. 2] J. Chem. Eng. Data 2006, 51, 2009-2015
48. 2] J. Chem. Thermodyn. 2005, 37, 888-899
49. Poling, B. E.; Prausnitz, J. M.; O'Connell, J. P. The Properties of Gases and Liquids; McGraw-Hill: New York, 2001.
50. Shereshefsky, J. L. Surface tension of saturated vapors and the equation of eotvos J. Phys. Chem. 1931, 35, 1712-1720
51. Guggenheim, E. A. The Principle of Correspondig States J. Chem. Phys. 1945, 13, 253-261
52. Rai, N.; Maginn, E. J. Vapor-Liquid Coexistence and Critical Behavior of Ionic Liquids via Molecular Simulations J. Phys. Chem. Lett. 2011, 2, 1439-1443