Vaporization enthalpy and cluster species in gas phase of 1,1,3,3-tetramethylguanidinium-based ionic liquids from computer simulations

AIChE Journal

Volumn 57, Issue 2, 2011, Pages 507-516

  Yu, Guangren ^a   Chen, Xiaochun ^a   Asumana, Charles ^a   Zhang, Suojiang ^b   Liu, Xiaomin ^b   Zhou, Guohui ^c  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

^b INSTITUTE OF PROCESS ENGINEERING   (China)

^c Beijing Shengjinqiao Information Technology Co Ltd   (China)

Author keywords

Ab initio calculation; Gas phase ion cluster; Ionic liquids; Molecular dynamics simulation; Vaporization enthalpy

Indexed keywords

AB INITIO; AB INITIO CALCULATIONS; GASPHASE; GUANIDINIUM-BASED IONIC LIQUIDS; IMIDAZOLIUM; INTERIONIC INTERACTIONS; ION PAIRS; LIQUID PHASE; LIQUID STATE; MOLECULAR CONFORMATION; MOLECULAR DYNAMIC SIMULATIONS; MOLECULAR DYNAMICS SIMULATION; NEUTRAL MOLECULES; STABLE SPECIES; STABLE TRIMERS; TETRAMERS; TETRAMETHYLGUANIDINIUM; THERMODYNAMICALLY STABLE; TRANSFER ENERGY; TRIFLUOROACETATES; VAPORIZATION ENTHALPIES; VAPORIZATION ENTHALPY;

CALCULATIONS; COMPUTER SIMULATION; DIMERS; ENTHALPY; GASES; IONS; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; PROTONS; VAN DER WAALS FORCES; VAPORIZATION;

IONIC LIQUIDS;

EID: 78650981336     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.12274     Document Type: Article

References (64)

1. Appleby D, Hussey CL, Seddon KR, Turp JE. Room-temperature ionic liquids as solvents for electronic absorption spectroscopy of halide complexes. Nature. 1986; 323: 614-616.
2. Hussey CL. Room temperature haloaluminate ionic liquids-novel solvents for transition metal solution chemistry. Pure Appl Chem. 1988; 60: 1763-1772.
3. Wilkes JS. A short history of ionic liquids-from molten salts to neoteric solvents. Green Chemistry. 2002; 4: 73-80.
4. Brennecke JF, Maginn EJ. Ionic liquids: innovative fluids for chemical processing. AIChE J. 2001; 47: 2384-2389.
5. Rogers RD, Seddon KR. Ionic liquids-Solvents of the future? Science. 2003; 302: 792-793.
6. Rogers RD, Seddon KR, editors. Ionic Liquids: Industrial Applications to Green Chemistry. Washington DC: Oxford University Press, 2002.
7. Rogers RD, Seddon KR, editors. Ionic Liquids as Green Solvents: Progress and Prospects. Washington, DC: Oxford University Press, 2002.
8. Seiler M, Jork C, Kavarnou A, Arlt W, Hirsch R. Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids. AIChE J. 2004; 50: 2439-2454.
9. Endres F. Ionic liquids: promising solvents for electrochemistry. Zeitschrift für Physikalische Chemie. 2004; 218: 255-283.
10. 4] ionic liquid. AIChE J. 2007; 53: 3108-3115.
11. Earle MJ, Esperanca JMSS, Gilea1 MA, Lopes JNC, Rebelo LPN, Magee JW, Seddon KR, Widegren JA. The distillation and volatility of ionic liquids. Nature. 2006; 439: 831-834.
12. Wasserscheid P. Volatility times for ionic liquids. Nature. 2006; 439: 797.
13. Paulechka YU, Zaitsau DH, Kabo GJ, Strechan AA. Vapor pressure and thermal stability of ionic liquid 1-butyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)amide. Thermochim Acta. 2005; 439: 158-160.
14. Zaitsau DH, Kabo GJ, Strechan AA, Paulechka YU, Tschersich A, Verevkin SP, Heintz A. Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids. J Phys Chem A. 2006; 110: 7303-7306.
15. Rebelo LPN, Lopes JNC, Esperancüa JMSS, Filipe E. On the critical temperature, normal boiling point, and vapor pressure of ionic liquids. J Phys Chem B. 2005; 109: 6040-6043.
16. Swiderski K, McLean A, Gordon CM, Vaughan DH. Estimates of internal energies of vaporisation of some room temperature ionic liquids. Chem Commun. 2004; 2178-2179.
17. Santos LMNBF, Lopes CJN, Coutinho JAP, Esperanca JMSS, Gomes LR, Marrucho IM, Rebelo LPN. Ionic liquids: first direct determination of their cohesive energy. J Am Chem Soc. 2007; 129: 284-285.
18. de Andrade J, Böes ES, Stassen H. A force field for liquid state simulations on room temperature molten salts: 1-ethyl-3-methylimidazolium tetrachloroaluminate. J Phys Chem B. 2002; 106: 3546-3548.
19. Liu ZP, Huang SP, Wang WC. A refined force field for molecular simulation of imidazolium-based ionic liquids. J Phys Chem B. 2004; 108: 12978-12989.
20. de Andrade J, Böes ES, Stassen H. Computational study of room temperature molten salts composed by 1-alkyl-3-methylimidazolium cations-Force-field proposal and validation. J Phys Chem B. 2002; 106: 13344-13351.
21. Morrow TI, Maginn EJ. Molecular dynamics study of the ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate. J Phys Chem B. 2002; 106: 12807-12813.
22. Micaelo NM, Baptista AM, Soares CM. Parametrization of 1-butyl-3-methylimidazolium hexafluorophosphate/nitrate ionic liquid for the GROMOS force field. J Phys Chem B. 2006; 110: 14444-14451.
23. Shah JK, Brennecke JF, Maginn EJ. Thermodynamic properties of the ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate from Monte Carlo simulations. Green Chem. 2002; 4: 112-118.
24. Cadena C, Maginn EJ. Molecular simulation study of some thermophysical and transport properties of triazolium-based ionic liquids. J Phys Chem B. 2006; 110: 18026-18039.
25. Cadena C, Zhao Q, Snurr RQ, Maginn EJ. Molecular modeling and experimental studies of the thermodynamic and transport properties of pyridinium-based ionic liquids. J Phys Chem B. 2006; 110: 2821-2832.
26. Kelkar MS, Maginn EJ. Calculating the enthalpy of vaporization for ionic liquid clusters. J Phys Chem B. 2007; 111: 9424-9427.
27. 3 molten salts. J Am Chem Soc. 1988; 110: 2722-2726.
28. 2. Raman scattering and ab initio calculations. Inorg Chem. 2001; 40: 2298-2304.
29. Meng Z, Dölle A, Carper WR. Gas phase model of an ionic liquid: semi-empirical and ab initio bonding and molecular structure. J Mol Struct (THEOCHEM). 2002; 585: 119-128.
30. Turner EA, Pye CC, Singer RD. Use of ab initio calculations toward the rational design of room temperature ionic liquids. J Phys Chem A. 2003; 107: 2277-2288.
31. Paulechka YU, Kabo GJ, Blokhin AV, Vydrov OA, Magee JW, Frenkel M. Thermodynamic properties of 1-butyl-3-methylimidazolium hexafluorophosphate in the ideal gas state. J Chem Eng Data. 2003; 48: 457-462.
32. Talaty ER, Raja S, Storhaug VJ, Dölle A, Carper WR. Raman and infrared spectra and ab initio calculations of C2-4mim imidazolium hexafluorophosphate ionic liquids. J Phys Chem B. 2004; 108: 13177-13184.
33. Hunt PA, Kirchner B, Welton T. Characterising the electronic structure of ionic liquids: an examination of the 1-butyl-3-methylimidazolium chloride ion pair. Chem Eur J. 2006; 12: 6762-6775.
34. Hunt PA, Gould IR. Structural characterization of the 1-butyl-3-methylimidazolium chloride ion pair using ab initio methods. J Phys Chem A. 2006; 110: 2269-2282.
35. Schmidt MW, Gordon Ms, Boatz JA. Triazolium-based energetic ionic liquids. J Phys Chem A. 2005; 109: 7285-7295.
36. Alavi S, Thompson DL. Proton transfer in gas-phase ammonium dinitramide clusters. J. Chem. Phys. 2003, 18: 25992605.
37. Bini R, Bortolini O, Chiappe C, Pieraccini D, Siciliano TJ. Development of cation/anion "interaction" scales for ionic liquids through ESI-MS measurements. J Phys Chem B. 2007; 111: 598-604.
38. Dupont J. On the solid, liquid and solution structural organization of imidazolium ionic liquids. J Braz Chem Soc. 2004; 15: 341-350.
39. AbdulSada AK, Elaiwi AE, Greenway AM, Seddon KR. Evidence for the clustering of substituted imidazolium salts via hydrogen bonding under the conditions of fast atom bombardment mass spectrometry. Eur Mass Spect. 1997; 3: 245-247.
40. Gozzo FC, Santos LS, Augusti R, Consorti CS, Dupont J, Eberlin MN. Gaseous supramolecules of imidazolium ionic liquids: "magic" numbers and intrinsic strengths of hydrogen bonds. Chem Eur J. 2004; 10: 6187-6193.
41. Xin X, Guo X, Duan H, Lin Y, Sun H. Efficient Knoevenagel condensation catalyzed by cyclic guanidinium lactate ionic liquid as medium. Catal Commun. 2007; 8: 115-117.
42. Fang S, Yang L, Wei C, Jiang C, Tachibana K, Kamijima K. Ionic liquids based on guanidinium cations and TFSI anion as potential electrolytes. Electrochim Acta. 2009; 54: 1752-1756.
43. Kulkarni PS, Branco LC, Crespo JG, Afonso CAM. A comparative study on absorption and selectivity of organic vapors by using ionic liquids based on imidazolium, quaternary ammonium, and guanidinium cations. Chem Eur J. 2007; 13: 8470-8477.
44. Mateus NMM, Branco LC, Lourenço NMT, Afonso CAM. Synthesis and properties of tetra-alkyl-dimethylguanidinium salts as a potential new generation of ionic liquids. Green Chem. 2003; 5: 347-352.
45. Xie H, Zhang S, Duan H. An ionic liquid based on a cyclic guanidinium cation is an efficient medium for the selective oxidation of benzyl alcohols. Tetrahedron Lett. 2004; 45: 2013-2015.
46. Gao H, Han B, Li J, Jiang T, Liu Z, Wu W, Chang Y. Preparation of room-temperature ionic liquids by neutralization of 1, 1, 3, 3-tetramethylguanidine with acids and their use as media for mannich reaction. Synth Commun. 2004; 34: 3083-3089.
47. 2 in 1-butyl-3-methylimidazolium hexafluorophosphate and 1, 1, 3, 3-tetramethylguanidium lactate at elevated pressures. J Chem Eng Data. 2005; 50: 1582-1585.
48. Yu G, Zhang S, Liu X, Zhou G, Chen X. Structure, interaction and property of amino-functionalized imidazolium ionic liquids by ab initio calculation and molecular dynamics simulation. AIChE J. 2007; 53: 3210-3221.
49. 2: a molecular orbital study. Ind Eng Chem Res. 2006; 45: 2875-2880.
50. Yu G, Zhang S. Insight into the cation-anion interaction in 1, 1, 3, 3-tetramethylguanidinium lactate ionic liquid. Fluid Phase Equilibria. 2007; 255: 86-92.
51. Liu X, Zhang S, Zhou G, Wu G, Yuan X, Yao X. New force field for molecular simulation of guanidinium-based ionic liquids. J Phys Chem B. 2006; 110: 12062-12071.
52. Zhou G, Liu X, Zhang S, Yu G, He H. A force field for molecular simulation of tetrabutylphosphonium amino acid ionic liquids. J Phys Chem B. 2007; 111: 7078-7084.
53. Dong K, Zhang S, Wang D, Yao X. Hydrogen bonds in imidazolium ionic liquids. J Phys Chem A. 2006; 110: 9775-9782.
54. Liu X, Zhou G, Zhang S. Molecular dynamics simulation of acyclic guanidinium-based ionic liquids. Fluid Phase Equilibria. 2008; 272: 1-7.
55. Lyubartsev AP, Laaksonen AM. DynaMix-a scalable portable parallel MD simulation package for arbitrary molecular mixtures. Comput Phys Commun. 2000; 128: 565-589.
56. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. GAUSSIAN 03 Revision C. 02. Wallingford CT: Gaussian, Inc., 2004.
57. Møller C, Plesset MS. Note on an approximation treatment for many-electron systems. Phys Rev. 1934; 46: 618-622.
58. Pople JA, Binkley JS, Seeger R. Theoretical models incorporating electron correlation. Int J Quantum Chem Symp. 1976; 10: 1-19.
59. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993; 98: 5648-5652.
60. Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988; 37: 785-789.
61. Dzyuba SV, Bartsch RA. 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.
62. Lide DR, editor. Handbook of Chemistry and Physics, 80th ed. Boca Raton, FL: CRC Press, 1999-2000.
63. Koch W, Holthausen MC. A Chemist's Guide to Density Functional Theory, 2nd ed. Weinheim, Germany: Wiley-VCH Verlag GmbH, 2001.
64. 2. J Phys Chem A. 1999; 103: 11328-11335.