Using Thermodynamics to Assess the Molecular Interactions of Tetrabutylphosphonium Carboxylate–Water Mixtures

Darius J. Yeadon; Johan Jacquemin; Natalia V. Plechkova; Margarida Costa Gomes; Kenneth R. Seddon

doi:10.1071/CH18481

RESEARCH ARTICLE

Previous Next Contents Vol 72(2)

Using Thermodynamics to Assess the Molecular Interactions of Tetrabutylphosphonium Carboxylate–Water Mixtures

Darius J. Yeadon

^A ^E , Johan Jacquemin ^A ^B ^E , Natalia V. Plechkova ^A , Margarida Costa Gomes ^C and Kenneth R. Seddon ^A ^D

+ Author Affiliations

- Author Affiliations

^A QUILL Research Centre, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, Northern Ireland, UK.

^B Université de Tours, Laboratoire PCM2E, Parc de Grandmont 37200, Tours, France.

^C Laboratoire de Chimie, Ecole Normale Supérieure de Lyon and CNRS, 46 allée d'Italie, 69364 Lyon Cedex 07, France.

^D Deceased.

^E Corresponding authors. Email: dyeadon01@qub.ac.uk; jj@univ-tours.fr

Australian Journal of Chemistry 72(2) 144-154 https://doi.org/10.1071/CH18481
Submitted: 28 September 2018 Accepted: 15 December 2018 Published: 17 January 2019

Abstract

Densities, ρ, viscosities, η, and enthalpies of mixing, , of binary [P_{4 4 4 4}][C_nCOO]–water mixtures (with n = 1, 2 or 7) were determined at atmospheric pressure as a function of temperature. The excess, , apparent, , and partial, , molar volumes were deduced from experimental data, as well as fragilities, m*, and excess Gibbs free energies of activation of viscous flow, . exhibited predominantly negative deviation from ideality, with a minimum at approximately ~0.8 for all three systems, indicating strong hydrogen-bonding interactions. All three binary systems were found to be fragile, with [P_{4 4 4 4}][C₇COO] showing the smallest deviations in fragility with the addition of water. values of the systems were exothermic over the entire composition range, having the following trend: [P_{4 4 4 4}][C₂COO] > [P_{4 4 4 4}][C₇COO] > [P_{4 4 4 4}][C₁COO].

References

[1] K. R. Seddon, J. Chem. Technol. Biotechnol. 1997, 68, 351.
| Crossref | GoogleScholarGoogle Scholar |

[2] M. Gaune-Escard, K. R. Seddon, Molten Salts and Ionic Liquids: Never the Twain 2010 (John Wiley & Sons: Hoboken, NJ).

[3] M. Freemantle, An Introduction to Ionic Liquids 2010 (Royal Society of Chemistry: Cambridge).

[4] M. Freemantle, Chem. Eng. News 1998, 76, 32.
| Crossref | GoogleScholarGoogle Scholar |

[5] R. D. Rogers, K. R. Seddon, Science 2003, 302, 792.
| Crossref | GoogleScholarGoogle Scholar | 14593156PubMed |

[6] J. Jacquemin, P. Nancarrow, D. W. Rooney, M. F. Costa Gomes, P. Husson, V. Majer, A. A. H. Pádua, C. Hardacre, J. Chem. Eng. Data 2008, 53, 2133.
| Crossref | GoogleScholarGoogle Scholar |

[7] J. Palomar, V. R. Ferro, J. S. Torrecilla, F. Rodríguez, Ind. Eng. Chem. Res. 2007, 46, 6041.
| Crossref | GoogleScholarGoogle Scholar |

[8] M. Deetlefs, K. R. Seddon, M. Shara, Phys. Chem. Chem. Phys. 2006, 8, 642.
| Crossref | GoogleScholarGoogle Scholar | 16482306PubMed |

[9] A. Varnek, N. Kireeva, I. V. Tetko, I. P. Baskin, V. P. Solov’ev, J. Chem. Inf. Model. 2007, 47, 1111.
| Crossref | GoogleScholarGoogle Scholar | 17381081PubMed |

[10] S. P. Ong, O. Andreussi, Y. Wu, N. Marzari, G. Ceder, Chem. Mater. 2011, 23, 2979.
| Crossref | GoogleScholarGoogle Scholar |

[11] R. L. Gardas, J. A. P. Coutinho, Fluid Phase Equilib. 2008, 265, 57.
| Crossref | GoogleScholarGoogle Scholar |

[12] Y. Kohno, H. Ohno, Chem. Commun. 2012, 7119.
| Crossref | GoogleScholarGoogle Scholar |

[13] R. Ludwig, Angew. Chem. Int. Ed. 2001, 40, 1808.
| Crossref | GoogleScholarGoogle Scholar |

[14] J. G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker, R. D. Rogers, Green Chem. 2001, 3, 156.
| Crossref | GoogleScholarGoogle Scholar |

[15] K. R. Seddon, A. Stark, M.-J. Torres, Pure Appl. Chem. 2000, 72, 2275.

[16] A. K. Abdul-Sada, A. M. Greenway, P. B. Hitchcock, T. J. Mohammed, K. R. Seddon, J. A. Zora, J. Chem. Soc. Chem. Commun. 1986, 1753.
| Crossref | GoogleScholarGoogle Scholar |

[17] P. A. Hunt, C. R. Ashworth, R. P. Matthews, Chem. Soc. Rev. 2015, 4, 1257.

[18] Y. Kohno, H. Ohno, Phys. Chem. Chem. Phys. 2012, 14, 5063.
| Crossref | GoogleScholarGoogle Scholar | 22334119PubMed |

[19] H. Ohno, K. Fujita, Y. Kohno, Phys. Chem. Chem. Phys. 2015, 17, 14454.
| Crossref | GoogleScholarGoogle Scholar | 25968477PubMed |

[20] K. Fujita, H. Ohno, Biopolymers 2010, 93, 1093.
| Crossref | GoogleScholarGoogle Scholar | 20665687PubMed |

[21] K. Fujita, D. R. MacFarlane, M. Forsyth, M. Yoshizawa-Fujita, K. Murata, N. Nakamura, H. Ohno, Biomacromolecules 2007, 8, 2080.
| Crossref | GoogleScholarGoogle Scholar | 17580947PubMed |

[22] K. Anderson, M. P. Atkins, J. Estager, Y. Kuah, S. Ng, A. A. Oliferenko, N. V. Plechkova, A. V. Puga, K. R. Seddon, D. F. Wassell, Green Chem. 2015, 17, 4340.
| Crossref | GoogleScholarGoogle Scholar |

[23] M. A. Varfolomeev, A. A. Khachatrian, B. S. Akhmadeev, B. N. Solomonov, Thermochim. Acta 2016, 633, 12.
| Crossref | GoogleScholarGoogle Scholar |

[24] J. Sun, J. Ren, S. Zhang, W. Cheng, Tetrahedron Lett. 2009, 50, 423.
| Crossref | GoogleScholarGoogle Scholar |

[25] D. Xu, Q. Yang, B. Su, Z. Bao, Q. Ren, H. Xing, J. Phys. Chem. B 2014, 118, 1071.
| Crossref | GoogleScholarGoogle Scholar | 24387657PubMed |

[26] K. J. Fraser, D. R. MacFarlane, Aust. J. Chem. 2009, 62, 309.
| Crossref | GoogleScholarGoogle Scholar |

[27] K. Tsunashima, M. Sugiya, Electrochem. Commun. 2007, 9, 2353.
| Crossref | GoogleScholarGoogle Scholar |

[28] G. M. Girard, M. Hilder, H. Zhu, D. Nucciarone, K. Whitbread, S. Zavorine, M. Moser, M. Forsyth, D. R. MacFarlane, P. C. Howlett, Phys. Chem. Chem. Phys. 2015, 17, 8706.
| Crossref | GoogleScholarGoogle Scholar | 25820549PubMed |

[29] S. Chowdhury, R. S. Mohan, J. L. Scott, Tetrahedron 2007, 63, 2363.
| Crossref | GoogleScholarGoogle Scholar |

[30] W. Hanhart, C. K. Ingold, J. Chem. Soc. 1927, 0, 997.
| Crossref | GoogleScholarGoogle Scholar |

[31] C. K. Ingold, C. C. N. Vass, J. Chem. Soc. 1928, 3125.

[32] C. J. Bradaric, A. Downard, C. Kennedy, A. J. Robertson, Y. Zhou, Green Chem. 2003, 5, 143.
| Crossref | GoogleScholarGoogle Scholar |

[33] H. Du, X. Qian, Carbohydr. Res. 2011, 346, 1985.
| Crossref | GoogleScholarGoogle Scholar | 21704309PubMed |

[34] R. Sescousse, K. A. Le, M. E. Ries, T. Budtova, J. Phys. Chem. B 2010, 114, 7222.
| Crossref | GoogleScholarGoogle Scholar | 20462222PubMed |

[35] M. T. Clough, K. Geyer, P. A. Hunt, S. Son, U. Vagt, T. Welton, Green Chem. 2015, 17, 231.
| Crossref | GoogleScholarGoogle Scholar |

[36] B. D. Rabideau, A. E. Ismail, Phys. Chem. Chem. Phys. 2015, 17, 5767.
| Crossref | GoogleScholarGoogle Scholar | 25627658PubMed |

[37] A. Xu, Y. Zhang, W. Lu, K. Yao, H. Xu, J. Mol. Liq. 2014, 197, 211.
| Crossref | GoogleScholarGoogle Scholar |

[38] Y. Qin, X. Lu, N. Sun, R. D. Rogers, Green Chem. 2010, 12, 968.
| Crossref | GoogleScholarGoogle Scholar |

[39] R. P. Swatloski, S. K. Spear, J. D. Holbrey, R. D. Rogers, J. Am. Chem. Soc. 2002, 124, 4974.
| Crossref | GoogleScholarGoogle Scholar | 11982358PubMed |

[40] N. R. Dhumal, H. J. Kim, J. Kiefer, J. Phys. Chem. A 2009, 113, 10397.
| Crossref | GoogleScholarGoogle Scholar | 19711961PubMed |

[41] M. J. Kamlet, R. Taft, J. Am. Chem. Soc. 1976, 98, 377.
| Crossref | GoogleScholarGoogle Scholar |

[42] C. Wang, H. Luo, D.-e. Jiang, H. Li, S. Dai, Angew. Chem. 2010, 122, 6114.
| Crossref | GoogleScholarGoogle Scholar |

[43] S. F. R. Taylor, C. McCrellis, C. McStay, J. Jacquemin, C. Hardacre, M. Mercy, R. G. Bell, N. H. de Leeuw, J. Solution Chem. 2015, 44, 511.
| Crossref | GoogleScholarGoogle Scholar |

[44] W. Wu, B. Han, H. Gao, Z. Liu, T. Jiang, J. Huang, Angew. Chem. Int. Ed. Engl. 2004, 43, 2415.
| Crossref | GoogleScholarGoogle Scholar | 15114577PubMed |

[45] K. Huang, D.-N. Cai, Y.-L. Chen, Y.-T. Wu, X.-B. Hu, Z.-B. Zhang, AIChE J. 2013, 59, 2227.
| Crossref | GoogleScholarGoogle Scholar |

[46] J. Palgunadi, S. Y. Hong, J. K. Lee, H. Lee, S. D. Lee, M. Cheong, H. S. Kim, J. Phys. Chem. B 2011, 115, 1067.
| Crossref | GoogleScholarGoogle Scholar | 21218815PubMed |

[47] S. Panda, V. Singh, N. Islam, R. L. Gardas, J. Mol. Liq. 2018, 259, 124.
| Crossref | GoogleScholarGoogle Scholar |

[48] S. Shahriari, L. C. Tomé, J. M. M. Araújo, L. P. N. Rebelo, J. A. P. Coutinho, I. M. Marrucho, M. G. Freire, RSC Adv. 2013, 3, 1835.
| Crossref | GoogleScholarGoogle Scholar |

[49] Z. Li, X. Liu, Y. Pei, J. Wang, M. He, Green Chem. 2012, 14, 2941.
| Crossref | GoogleScholarGoogle Scholar |

[50] R. Ferreira, H. Garcia, A. F. Sousa, M. Petkovic, P. Lamosa, C. S. R. Freire, A. J. D. Silvestre, L. P. N. Rebelo, C. S. Pereira, New J. Chem. 2012, 36, 2014.
| Crossref | GoogleScholarGoogle Scholar |

[51] R. Ferreira, H. Garcia, A. F. Sousa, M. Guerreiro, F. J. S. Duarte, C. S. R. Freire, M. J. Calhorda, A. J. D. Silvestre, W. Kunz, L. P. N. Rebelo, C. S. Pereira, RSC Adv. 2014, 4, 2993.
| Crossref | GoogleScholarGoogle Scholar |

[52] L. C. Tome, D. J. S. Patinha, R. Ferreira, H. Garcia, C. Silva Pereira, C. S. Freire, L. P. N. Rebelo, I. M. Marrucho, ChemSusChem 2014, 7, 110.
| Crossref | GoogleScholarGoogle Scholar | 24458737PubMed |

[53] K. Oster, P. Goodrich, J. Jacquemin, C. Hardacre, A. P. C. Ribeiro, A. Elsinawi, J. Chem. Thermodyn. 2018, 121, 97.
| Crossref | GoogleScholarGoogle Scholar |

[54] M. Anouti, A. Vigeant, J. Jacquemin, C. Brigouleix, D. Lemordant, J. Chem. Thermodyn. 2010, 42, 834.
| Crossref | GoogleScholarGoogle Scholar |

[55] M. Anouti, M. Caillon-Caravanier, Y. Dridi, J. Jacquemin, C. Hardacre, D. Lemordant, J. Chem. Thermodyn. 2009, 41, 799.
| Crossref | GoogleScholarGoogle Scholar |

[56] D. J. S. Patinha, L. C. Tomé, H. Garcia, R. Ferreira, C. S. Pereira, L. P. N. Rebelo, I. M. Marrucho, J. Chem. Thermodyn. 2015, 84, 93.
| Crossref | GoogleScholarGoogle Scholar |

[57] M. Anouti, J. Jacquemin, D. Lemordant, J. Chem. Eng. Data 2010, 55, 5719.
| Crossref | GoogleScholarGoogle Scholar |

[58] S. Stevanovic, A. Podgorsek, A. A. Padua, M. F. Costa Gomes, J. Phys. Chem. B 2012, 116, 14416.
| Crossref | GoogleScholarGoogle Scholar | 23145571PubMed |

[59] V. H. Alvarez, S. Mattedi, M. Martin-Pastor, M. Aznar, M. Iglesias, J. Chem. Thermodyn. 2011, 43, 997.
| Crossref | GoogleScholarGoogle Scholar |

[60] M. S. Santosh, D. K. Bhat, Fluid Phase Equilib. 2010, 298, 169.
| Crossref | GoogleScholarGoogle Scholar |

[61] P. J. Carvalho, T. Regueira, L. M. N. B. F. Santos, J. Fernandez, J. A. P. Coutinho, J. Chem. Eng. Data 2010, 55, 645.
| Crossref | GoogleScholarGoogle Scholar |

[62] L. A. S. Ries, F. A. do Amaral, K. Matos, E. M. A. Martini, M. O. de Souza, R. F. de Souza, Polyhedron 2008, 27, 3287.
| Crossref | GoogleScholarGoogle Scholar |

[63] A. Xu, J. Wang, H. Wang, Green Chem. 2010, 12, 268.
| Crossref | GoogleScholarGoogle Scholar |

[64] K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. Int. Ed. Engl. 2008, 47, 8731.
| Crossref | GoogleScholarGoogle Scholar | 18846527PubMed |

[65] N. Muhammad, M. I. Hossain, Z. Man, M. El-Harbawi, M. A. Bustam, Y. A. Noaman, N. B. M. Alitheen, M. K. Ng, G. Hefter, C.-Y. Yin, J. Chem. Eng. Data 2012, 57, 2191.
| Crossref | GoogleScholarGoogle Scholar |

[66] M. C. Ribeiro, A. A. Padua, M. F. Gomes, J. Chem. Phys. 2014, 140, 244514.
| Crossref | GoogleScholarGoogle Scholar | 24985661PubMed |

[67] C. Angell, J. Non-Cryst. Solids 1985, 131, 13.

[68] R. Böhmer, K. L. Ngai, C. A. Angell, D. J. Plazek, J. Chem. Phys. 1993, 99, 4201.
| Crossref | GoogleScholarGoogle Scholar |

[69] C. A. Angell, J. Phys. Chem. Solids 1988, 49, 863.
| Crossref | GoogleScholarGoogle Scholar |

[70] J. Leys, M. Wubbenhorst, C. Preethy Menon, R. Rajesh, J. Thoen, C. Glorieux, P. Nockemann, B. Thijs, K. Binnemans, S. Longuemart, J. Chem. Phys. 2008, 128, 064509.
| Crossref | GoogleScholarGoogle Scholar | 18282058PubMed |

[71] P. Sippel, V. Dietrich, D. Reuter, M. Aumüller, P. Lunkenheimer, A. Loidl, S. Krohns, J. Mol. Liq. 2016, 223, 635.
| Crossref | GoogleScholarGoogle Scholar |

[72] P. Sippel, P. Lunkenheimer, S. Krohns, E. Thoms, A. Loidl, Sci. Rep. 2015, 5, 13922.
| Crossref | GoogleScholarGoogle Scholar | 26355037PubMed |

[73] K. M. Dieter, C. J. Dymek, N. E. Heimer, J. W. Rovang, J. S. Wilkes, J. Am. Chem. Soc. 1988, 110, 2722.
| Crossref | GoogleScholarGoogle Scholar |

[74] W. Shi, K. Damodaran, H. B. Nulwala, D. R. Luebke, Phys. Chem. Chem. Phys. 2012, 14, 15897.
| Crossref | GoogleScholarGoogle Scholar | 23093293PubMed |

[75] P. A. Hunt, J. Phys. Chem. B 2007, 111, 4844.
| Crossref | GoogleScholarGoogle Scholar | 17388550PubMed |

[76] R. J. Bearman, P. F. Jones, J. Chem. Phys. 1960, 33, 1432.
| Crossref | GoogleScholarGoogle Scholar |

[77] U. R. Kapadi, D. G. Hundiwale, N. B. Patil, M. K. Lande, P. R. Patil, Fluid Phase Equilib. 2001, 192, 63.
| Crossref | GoogleScholarGoogle Scholar |

[78] N. Ouerfelli, Z. Barhoumi, R. Besbes, N. Amdouni, Phys. Chem. Liquids 2011, 49, 777.
| Crossref | GoogleScholarGoogle Scholar |

[79] A. Saul, W. Wagner, J. Phys. Chem. Ref. Data 1989, 18, 1537.
| Crossref | GoogleScholarGoogle Scholar |

[80] A. Podgorsek, J. Jacquemin, A. A. Padua, M. F. Costa Gomes, Chem. Rev. 2016, 116, 6075.
| Crossref | GoogleScholarGoogle Scholar | 27144455PubMed |

[81] X.-X. Ma, L. Li, J. Wei, W.-B. Duan, W. Guan, J.-Z. Yang, J. Chem. Eng. Data 2012, 57, 3171.
| Crossref | GoogleScholarGoogle Scholar |

[82] X.-X. Ma, Q.-B. Zhang, J. Wei, Y. Pan, W. Guan, J.-Z. Yang, J. Chem. Thermodyn. 2013, 65, 91.
| Crossref | GoogleScholarGoogle Scholar |

[83] A. Podgoršek, A. S. Pensado, C. C. Santini, M. F. Costa Gomes, A. A. H. Pádua, J. Phys. Chem. C 2013, 117, 3537.
| Crossref | GoogleScholarGoogle Scholar |

[84] J.-Z. Yang, Z.-H. Zhang, D.-W. Fang, J.-G. Li, W. Guan, J. Tong, Fluid Phase Equilib. 2006, 247, 80.
| Crossref | GoogleScholarGoogle Scholar |

[85] L. E. Ficke, H. Rodríguez, J. F. Brennecke, J. Chem. Eng. Data 2008, 53, 2112.
| Crossref | GoogleScholarGoogle Scholar |

[86] W. Guan, W.-F. Xue, J. Tong, C.-X. Wang, J.-Z. Yang, J. Solution Chem. 2009, 38, 1463.
| Crossref | GoogleScholarGoogle Scholar |

[87] W. Guan, W.-F. Xue, N. Li, J. Tong, J. Chem. Eng. Data 2008, 53, 1401.
| Crossref | GoogleScholarGoogle Scholar |

[88] Z.-F. Zhang, J.-G. Li, Q.-G. Zhang, W. Guan, J.-Z. Yang, J. Chem. Eng. Data 2008, 53, 1196.
| Crossref | GoogleScholarGoogle Scholar |

[89] W. Guan, L. Li, X.-X. Ma, J. Tong, D.-W. Fang, J.-Z. Yang, J. Chem. Thermodyn. 2012, 47, 209.
| Crossref | GoogleScholarGoogle Scholar |

[90] L. F. Lepre, J. Szala-Bilnik, A. A. Padua, M. Traikia, R. A. Ando, M. F. Costa Gomes, Phys. Chem. Chem. Phys. 2016, 18, 23285.
| Crossref | GoogleScholarGoogle Scholar | 27498753PubMed |

[91] D. Constantinescu, K. Schaber, F. Agel, M. H. Klingele, T. J. S. Schubert, J. Chem. Eng. Data 2007, 52, 1280.
| Crossref | GoogleScholarGoogle Scholar |

[92] Z. He, Z. Zhao, X. Zhang, H. Feng, Fluid Phase Equilib. 2010, 298, 83.
| Crossref | GoogleScholarGoogle Scholar |

[93] J. Ren, Z. Zhao, X. Zhang, J. Chem. Thermodyn. 2011, 43, 576.
| Crossref | GoogleScholarGoogle Scholar |

[94] L. E. Ficke, R. R. Novak, J. F. Brennecke, J. Chem. Eng. Data 2010, 55, 4946.
| Crossref | GoogleScholarGoogle Scholar |

[95] L. P. N. Rebelo, V. Najdanovic-Visak, Z. P. Visak, M. Nunes da Ponte, J. Szydlowski, C. A. Cerdeiriña, J. Troncoso, L. Romaní, J. M. S. S. Esperança, H. J. R. Guedes, H. C. de Sousa, Green Chem. 2004, 6, 369.
| Crossref | GoogleScholarGoogle Scholar |

[96] M. G. Freire, C. M. Neves, I. M. Marrucho, J. A. Coutinho, A. M. Fernandes, J. Phys. Chem. A 2010, 114, 3744.
| Crossref | GoogleScholarGoogle Scholar | 20235600PubMed |

[97] L. E. Ficke, J. F. Brennecke, J. Phys. Chem. B 2010, 114, 10496.
| Crossref | GoogleScholarGoogle Scholar | 20701381PubMed |

[98] J. Jacquemin, P. Goodrich, W. Jiang, D. W. Rooney, C. Hardacre, J. Phys. Chem. B 2013, 117, 1938.
| Crossref | GoogleScholarGoogle Scholar | 23320846PubMed |

[99] P. S. Campbell, A. Podgorsek, T. Gutel, C. C. Santini, A. A. H. Padua, M. F. Costa Gomes, F. Bayard, B. Fenet, Y. Chauvin, J. Phys. Chem. B 2010, 114, 8156.
| Crossref | GoogleScholarGoogle Scholar | 20504005PubMed |

[100] L. F. Lepre, L. Pison, L. J. A. Siqueira, R. A. Ando, M. F. Costa Gomes, Separ. Purif. Tech. 2018, 196, 10.
| Crossref | GoogleScholarGoogle Scholar |

Using Thermodynamics to Assess the Molecular Interactions of Tetrabutylphosphonium Carboxylate–Water Mixtures

Abstract

References

Subscriber Login