Solubility of sugars and sugar alcohols in ionic liquids: Measurement and PC-SAFT modeling

Journal of Physical Chemistry B

Volumn 117, Issue 34, 2013, Pages 9980-9995

  Carneiro, Aristides P ^a   Held, Christoph ^b   Rodríguez, Oscar ^a,c   Sadowski, Gabriele ^b   Macedo, Eugénia A ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b TU DORTMUND UNIVERSITY   (Germany)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACCURATE MODELING; BINARY INTERACTION PARAMETER; INFINITE DILUTION; IONIC LIQUID (ILS); REASONABLE ACCURACY; THERMODYNAMIC APPROACHES; TRIFLUOROACETATES; TRIHEXYLTETRADECYLPHOSPHONIUM;

IONIC LIQUIDS; POLYOLS; PROPANOL; REFINING; SUGAR SUBSTITUTES; SUGARS;

SOLUBILITY;

EID: 84883314985     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp404864c     Document Type: Article

References (86)

1. Paduszyński; et al. J. Phys. Chem. B 2013, 117, 7034-7046
2. Werpy, T. A.; Petersen, G. Top Value Added Chemicals From Biomass: I. Results of Screening for Potential Candidates from Sugars and Synthesis Gas; Pacific Northwest National Laboratory: Richland, WA, 2004.
3. Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 37, 123-150
4. Zhao, H.; Xia, S. Q.; Ma, P. S. Use of Ionic Liquids As 'Green' Solvents for Extractions J. Chem. Technol. Biotechnol. 2005, 80, 1089-1096
5. Zhao, D. B.; Wu, M.; Kou, Y.; Min, E. Ionic Liquids: Applications in Catalysis Catal. Today 2002, 74, 157-189
6. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2083
7. Brennecke, J. F.; Maginn, E. J. Ionic Liquids: Innovative Fluids for Chemical Processing AIChE J. 2001, 47, 2384-2389
8. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room Temperature Ionic Liquids As Novel Media for 'Clean' Liquid-Liquid Extraction Chem. Commun. 1998, 1765-1766
9. Tan, S. S. Y.; MacFarlane, D. R. Ionic Liquids in Biomass Processing Top. Curr. Chem. 2009, 290, 311-339
10. da Costa Lopes, A.; João, K.; Morais, A.; Bogel-Łukasik, E.; Bogel-Łukasik, R. Ionic Liquids As a Tool for Lignocellulosic Biomass Fractionation Sustainable Chem. Process 2013, 1, 1-31
11. Sun, N.; Rodriguez, H.; Rahman, M.; Rogers, R. D. Where Are Ionic Liquid Strategies Most Suited in the Pursuit of Chemicals and Energy from Lignocellulosic Biomass? Chem. Commun. 2011, 47, 1405-1421
12. da Costa Lopes, A. M.; João, K. G.; Rubik, D. F.; Bogel-Łukasik, E.; Duarte, L. C.; Andreaus, J.; Bogel-Łukasik, R. Pre-treatment of Lignocellulosic Biomass Using Ionic Liquids: Wheat Straw Fractionation Bioresour. Technol. 2013, 142, 198-208
13. Long, J.; Li, X.; Guo, B.; Wang, L.; Zhang, N. Catalytic Delignification of Sugarcane Bagasse in the Presence of Acidic Ionic Liquids Catal. Today 2013, 200, 99-105
14. Shill, K.; Padmanabhan, S.; Xin, Q.; Prausnitz, J. M.; Clark, D. S.; Blanch, H. W. Ionic Liquid Pretreatment of Cellulosic Biomass: Enzymatic Hydrolysis and Ionic Liquid Recycle Biotechnol. Bioeng. 2011, 108, 511-520
15. Iguchi, M.; Aida, T. M.; Watanabe, M.; Smith, R. L. Dissolution and Recovery of Cellulose from 1-Butyl-3-methylimidazolium Chloride in Presence of Water Carbohydr. Polym. 2013, 92, 651-658
16. Moreau, C.; Finiels, A.; Vanoye, L. Dehydration of Fructose and Sucrose into 5-Hydroxymethylfurfural in the Presence of 1-H-3-methyl Imidazolium Chloride Acting Both As Solvent and Catalyst J. Mol. Catal. A: Chem. 2006, 253, 165-169
17. Forsyth, S. A.; MacFarlane, D. R.; Thomson, R. J.; von Itzstein, M. Rapid, Clean, And Mild O-Acetylation of Alcohols and Carbohydrates in an Ionic Liquid Chem. Commun. 2002, 714-715
18. Forsyth, S. A.; MacFarlane, D. R. 1-Alkyl-3-methylbenzotriazolium Salts: Ionic Solvents and Electrolytes J. Mater. Chem. 2003, 13, 2451-2456
19. Liu, Q.; Janssen, M. H. A.; van Rantwijk, F.; Sheldon, R. A. Room-Temperature Ionic Liquids That Dissolve Carbohydrates in High Concentrations Green Chem. 2005, 7, 39
20. Lee, S. H.; Dang, D. T.; Ha, S. H.; Chang, W.-J.; Koo, Y.-M. Lipase-Catalyzed Synthesis of Fatty Acid Sugar Ester Using Extremely Supersaturated Sugar Solution in Ionic Liquids Biotechnol. Bioeng. 2008, 99, 1-8
21. Zhao, H.; Baker, G. A.; Song, Z.; Olubajo, O.; Crittle, T.; Peters, D. Designing Enzyme-Compatible Ionic Liquids That Can Dissolve Carbohydrates Green Chem. 2008, 10, 696
22. Rosatella, A. A.; Branco, L. C.; Afonso, C. A. M. Studies on Dissolution of Carbohydrates in Ionic Liquids and Extraction from Aqueous Phase Green Chem. 2009, 11, 1406-1413
23. Carneiro, A. P.; Rodriguez, O.; Macedo, E. A. Solubility of Monosaccharides in Ionic Liquids-Experimental Data and Modeling Fluid Phase Equilib. 2012, 314, 22-28
24. Conceiçao, 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
25. Paduszyński, K.; Okuniewski, M.; Domańska, U. Renewable Feedstocks in Green Solvents: Thermodynamic Study on Phase Diagrams of d-Sorbitol and Xylitol with Dicyanamide Based Ionic Liquids J. Phys. Chem. B 2013, 117, 7034-7046
26. Carneiro, A. P.; Rodriguez, O.; Macedo, E. A. Solubility of Xylitol and Sorbitol in Ionic Liquids-Experimental Data and Modeling J. Chem. Thermodyn. 2012, 55, 184-192
27. Carneiro, A. P.; Rodríguez, O.; Macedo, E. A. Fructose and Glucose Dissolution in Ionic Liquids: Solubility and Thermodynamic Modeling Ind. Eng. Chem. Res. 2013, 52, 3424-3435
28. Payne, S. M.; Kerton, F. M. Solubility of Bio-Sourced Feedstocks in 'Green' Solvents Green Chem. 2010, 12, 1648-1653
29. Zakrzewska, M. E.; Bogel-Lukasik, E.; Bogel-Lukasik, R. Solubility of Carbohydrates in Ionic Liquids Energy Fuels 2010, 24, 737-745
30. Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures AIChE J. 1968, 14, 135-144
31. Abrams, D. S.; Prausnitz, J. M. Statistical Thermodynamics of Liquid-Mixtures-New Expression for Excess Gibbs Energy of Partly or Completely Miscible Systems AIChE J. 1975, 21, 116-128
32. Feng, W.; Vanderkooi, H.; Deswaanarons, J. Application of the SAFT Equation of State to Biomass Fast Pyrolysis Liquid Chem. Eng. Sci. 2005, 60, 617-624
33. Huang, S. H.; Radosz, M. Equation of State for Small, Large, Polydisperse, and Associating Molecules Ind. Eng. Chem. Res. 1990, 29, 2284-2294
34. Ji, P. J.; Feng, W.; Tan, T. W. Density Calculation of Sugar Solutions with the SAFT Model J. Chem. Eng. Data 2007, 52, 135-140
35. Ji, P. J.; Feng, W.; Tan, T. W.; Zheng, D. X. Modeling of Water Activity, Oxygen Solubility and Density of Sugar and Sugar Alcohol Solutions Food Chem. 2007, 104, 551-558
36. Held, C.; Carneiro, A. P.; Rodríguez, O.; Sadowski, G.; Macedo, E. A. Modeling Thermodynamic Properties of Aqueous Single-Solute and Multi-Solute Sugar Solutions with PC-SAFT AIChE J. 2013, 10.1002/aic.14212
37. Maia, F. M.; Tsivintzelis, I.; Rodriguez, O.; Macedo, E. A.; Kontogeorgis, G. M. Equation of State Modelling of Systems with Ionic Liquids: Literature Review and Application with the Cubic Plus Association (CPA) Model Fluid Phase Equilib. 2012, 332, 128-143
38. Vega, L. F.; Vilaseca, O.; Llovell, F.; Andreu, J. S. Modeling Ionic Liquids and the Solubility of Gases in Them: Recent Advances and Perspectives Fluid Phase Equilib. 2010, 294, 15-30
39. Kroon, M. C.; Karakatsani, E. K.; Economou, I. G.; Witkamp, G. J.; Peters, C. J. Modeling of the Carbon Dioxide Solubility in Imidazolium-Based Ionic Liquids with the tPC-PSAFT Equation of State J. Phys. Chem. B 2006, 110, 9262-9269
40. Nann, A.; Mündges, J.; Held, C.; Verevkin, S. P.; Sadowski, G. Molecular Interactions in 1-Butanol + IL Solutions by Measuring and Modeling Activity Coefficients J. Phys. Chem. B 2013, 117, 3173-3185
41. Domańska, U.; Zawadzki, M.; Paduszynski, K.; Krolikowski, M. Perturbed-Chain SAFT as a Versatile Tool for Thermodynamic Modeling of Binary Mixtures Containing Isoquinolinium Ionic Liquids J. Phys. Chem. B 2012, 116, 8191-8200
42. Chen, Y. S.; Mutelet, F.; Jaubert, J. N. Modeling the Solubility of Carbon Dioxide in Imidazolium-Based Ionic Liquids with the PC-SAFT Equation of State J. Phys. Chem. B 2012, 116, 14375-14388
43. 2 in Ionic Liquids by a Simple Model J. Phys. Chem. C 2007, 111, 16028-16034
44. Ashrafmansouri, S. S.; Raeissi, S. Modeling Gas Solubility in Ionic Liquids with the SAFT-Gamma Group Contribution Method J. Supercrit. Fluids 2012, 63, 81-91
45. Rahmati-Rostami, M.; Behzadi, B.; Ghotbi, C. Thermodynamic Modeling of Hydrogen Sulfide Solubility in Ionic Liquids Using Modified SAFT-VR and PC-SAFT Equations of State Fluid Phase Equilib. 2011, 309, 179-189
46. Ji, X.; Adidharma, H. Thermodynamic Modeling of Ionic Liquid Density with Heterosegmented Statistical Associating Fluid Theory Chem. Eng. Sci. 2009, 64, 1985-1992
47. Ji, X.; Held, C.; Sadowski, G. Modeling Imidazolium-Based Ionic Liquids with ePC-SAFT Fluid Phase Equilib. 2012, 335, 64-73
48. Paduszyński, K.; Domańska, U. Solubility of Aliphatic Hydrocarbons in Piperidinium Ionic Liquids: Measurements and Modeling in Terms of Perturbed-Chain Statistical Associating Fluid Theory and Nonrandom Hydrogen-Bonding Theory J. Phys. Chem. B 2011, 115, 12537-12548
49. Gross, J.; Sadowski, G. Perturbed-Chain SAFT: An Equation of State Based on a Perturbation Theory for Chain Molecules Ind. Eng. Chem. Res. 2001, 40, 1244-1260
50. Shi, C.; Ge, Q.; Zhou, F.; Cai, M.; Wang, X.; Fang, X.; Pan, X. An Improved Preparation of 3-Ethyl-1-methylimidazolium Trifluoroacetate and Its Application in Dye Sensitized Solar Cells Solar Energy 2009, 83, 108-112
51. Kulkarni, P. S.; Branco, L. C.; Crespo, J. G.; Nunes, M. C.; Raymundo, A.; Afonso, C. A. M. Comparison of Physicochemical Properties of New Ionic Liquids Based on Imidazolium, Quaternary Ammonium, and Guanidinium Cations Chem.-Eur. J. 2007, 13, 8478-8488
52. 2N] Ionic Liquids: Predictions from the Soft-SAFT Equation J. Phys. Chem. B 2011, 115, 4387-4398
53. Youngs, T. G. A.; Holbrey, J. D.; Mullan, C. L.; Norman, S. E.; Lagunas, M. C.; D'Agostino, C.; Mantle, M. D.; Gladden, L. F.; Bowron, D. T.; Hardacre, C. Neutron Diffraction, NMR and Molecular Dynamics Study of Glucose Dissolved in the Ionic Liquid 1-Ethyl-3-methylimidazolium Acetate Chem. Sci. 2011, 2, 1594-1605
54. Remsing, R. C.; Hernandez, G.; Swatloski, R. P.; Massefski, W. W.; Rogers, R. D.; Moyna, G. Solvation of Carbohydrates in N, N '-Dialkylimidazolium Ionic Liquids: A Multinuclear NMR Spectroscopy Study J. Phys. Chem. B 2008, 112, 11071-11078
55. Wolbach, J. P.; Sandler, S. I. Using Molecular Orbital Calculations to Describe the Phase Behavior of Cross-Associating Mixtures Ind. Eng. Chem. Res. 1998, 37, 2917-2928
56. Prausnitz, J. M.; Lichtenthaler, R. N.; Azevedo, E. G. Molecular Thermodynamics of Fluid-Phase Equilibria, 3rd ed.; Prentice Hall: Upper Saddle River, NJ, 1999.
57. Raemy, A.; Schweizer, T. F. Thermal Behaviour of Carbohydrates Studied by Heat Flow Calorimetry J. Therm. Anal. 1983, 28, 95-108
58. Roos, Y. Melting and Glass Transitions of Low Molecular Weight Carbohydrates Carbohydr. Res. 1993, 238, 39-48
59. Ferreira, O.; Brignole, E. A.; Macedo, E. A. Phase Equilibria in Sugar Solutions Using the A-UNIFAC Model Ind. Eng. Chem. Res. 2003, 42, 6212-6222
60. Catté, M.; Dussap, C.-G.; Achard, C.; Gros, J.-B. Excess Properties and Solid-Liquid Equilibria for Aqueous Solutions of Sugars Using a UNIQUAC Model Fluid Phase Equilib. 1994, 96, 33-50
61. Tong, B.; Tan, Z.-C.; Shi, Q.; Li, Y.-S.; Yue, D.-T.; Wang, S.-X. Thermodynamic Investigation of Several Natural Polyols (I): Heat Capacities and Thermodynamic Properties of Xylitol Thermochim. Acta 2007, 457, 20-26
62. Yaws, C. L. Yaws' Handbook of Thermodynamic and Physical Properties of Chemical Compounds; Knovel: New York, 2003
63. Mota, F. L.; Queimada, A. J.; Pinho, S. P.; Macedo, E. A. Water Solubility of Drug-Like Molecules with the Cubic-Plus-Association Equation of State Fluid Phase Equilib. 2010, 298, 75-82
64. 2 Ionic Liquids (n =2, 3, and 4) at T =323.15 K J. Chem. Thermodyn. 2011, 43, 1256-1262
65. Calvar, N.; Gomez, E.; Dominguez, A.; Macedo, E. A. Vapour Pressures, Osmotic and Activity Coefficients for Binary Mixtures Containing (1-Ethylpyridinium Ethylsulfate Plus Several Alcohols) at T =323.15 K J. Chem. Thermodyn. 2010, 42, 625-630
66. Calvar, N.; Gonzalez, B.; Dominguez, A.; Macedo, E. A. Osmotic Coefficients of Binary Mixtures of 1-Butyl-3-methylimidazolium Methylsulfate and 1,3-Dimethylimidazolium Methylsulfate with Alcohols at T =323.15 K J. Chem. Thermodyn. 2009, 41, 617-622
67. Gomez, E.; Gonzalez, B.; Calvar, N.; Tojo, E.; Dominguez, A. Physical Properties of Pure 1-Ethyl-3-methylimidazolium Ethylsulfate and Its Binary Mixtures with Ethanol and Water at Several Temperatures J. Chem. Eng. Data 2006, 51, 2096-2102
68. Rodríguez, H.; Brennecke, J. F. Temperature and Composition Dependence of the Density and Viscosity of Binary Mixtures of Water + Ionic Liquid J. Chem. Eng. Data 2006, 51, 2145-2155
69. González, E. J.; González, B.; Calvar, N.; Domínguez, á. Physical Properties of Binary Mixtures of the Ionic Liquid 1-Ethyl-3-methylimidazolium Ethyl Sulfate with Several Alcohols at T = (298.15, 313.15, and 328.15) K and Atmospheric Pressure J. Chem. Eng. Data 2007, 52, 1641-1648
70. Hofman, T.; Goldon, A.; Nevines, A.; Letcher, T. M. Densities, Excess Volumes, Isobaric Expansivity, And Isothermal Compressibility of the (1-Ethyl-3-methylimidazolium Ethylsulfate Plus Methanol) System at Temperatures (283.15 to 333.15) K and Pressures from (0.1 to 35) MPa J. Chem. Thermodyn 2008, 40, 580-591
71. Wong, C. L.; Soriano, A. N.; Li, M. H. Diffusion Coefficients and Molar Conductivities in Aqueous Solutions of 1-Ethyl-3-methylimidazolium-Based Ionic Liquids Fluid Phase Equilib. 2008, 271, 43-52
72. Sumartschenkowa, I. A.; Verevkin, S. P.; Vasiltsova, T. V.; Bich, E.; Heintz, A.; Shevelyova, M. P.; Kabo, G. J. Experimental Study of Thermodynamic Properties of Mixtures Containing Ionic Liquid 1-Ethyl-3-methylimidazolium Ethyl Sulfate Using Gas-Liquid Chromatography and Transpiration Method J. Chem. Eng. Data 2006, 51, 2138-2144
73. Quijada-Maldonado, E.; van der Boogaart, S.; Lijbers, J. H.; Meindersma, G. W.; de Haan, A. B. Experimental Densities, Dynamic Viscosities and Surface Tensions of the Ionic Liquids Series 1-Ethyl-3-methylimidazolium Acetate and Dicyanamide and Their Binary and Ternary Mixtures with Water and Ethanol at T = (298.15 to 343.15 K) J. Chem. Thermodyn. 2012, 51, 51-58
74. 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 2010, 55, 1784-1788
75. Mutelet, F.; Revelli, A. L.; Jaubert, J. N.; Sprunger, L. M.; Acree, W. E.; Baker, G. A. Partition Coefficients of Organic Compounds in New Imidazolium and Tetralkylammonium Based Ionic Liquids Using Inverse Gas Chromatography J. Chem. Eng. Data 2010, 55, 234-242
76. Domańska, U.; Marciniak, A. Activity Coefficients at Infinite Dilution Measurements for Organic Solutes and Water in the Ionic Liquid 1-Ethyl-3-methylimidazolium Trifluoroacetate J. Phys. Chem. B 2007, 111, 11984-11988
77. Fredlake, C. P.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. Thermophysical Properties of Imidazolium-Based Ionic Liquids J. Chem. Eng. Data 2004, 49, 954-964
78. Sanchez, L. G.; Espel, J. R.; Onink, F.; Meindersma, G. W.; de Haan, A. B. Density, Viscosity, and Surface Tension of Synthesis Grade Imidazolium, Pyridinium, and Pyrrolidinium Based Room Temperature Ionic Liquids J. Chem. Eng. Data 2009, 54, 2803-2812
79. Carvalho, P. J.; Regueira, T.; Santos, L. M. N. B. F.; Fernandez, J.; Coutinho, J. A. P. Effect of Water on the Viscosities and Densities of 1-Butyl-3-methylimidazolium Dicyanamide and 1-Butyl-3-methylimidazolium Tricyanomethane at Atmospheric Pressure J. Chem. Eng. Data 2010, 55, 645-652
80. 3] and [Aliquat][dca] Fluid Phase Equilib. 2010, 294, 157-179
81. Pereiro, A. B.; Veiga, H. I. M.; Esperanca, J. M. S. S.; Rodriguez, A. Effect of Temperature on the Physical Properties of Two Ionic Liquids J. Chem. Thermodyn. 2009, 41, 1419-1423
82. Rodriguez, H.; Brennecke, J. F. Temperature and Composition Dependence of the Density and Viscosity of Binary Mixtures of Water Plus Ionic Liquid J. Chem. Eng. Data 2006, 51, 2145-2155
83. Jacquemin, J.; Ge, R.; Nancarrow, P.; Rooney, D. W.; Gomes, M. F. C.; Padua, A. A. H.; Hardacre, C. Prediction of Ionic Liquid Properties. I. Volumetric Properties As a Function of Temperature at 0.1 MPa J. Chem. Eng. Data 2008, 53, 716-726
84. Emel'yanenko, V. N.; Verevkin, S. P.; Heintz, A. The Gaseous Enthalpy of Formation of the Ionic Liquid 1-Butyl-3-methylimidazolium Dicyanamide from Combustion Calorimetry, Vapor Pressure Measurements, And Ab Initio Calculations J. Am. Chem. Soc. 2007, 129, 3930-3937
85. Calvar, N.; Gonzalez, B.; Dominguez, A.; Macedo, E. A. Osmotic Coefficients of Binary Mixtures of Four Ionic Liquids with Ethanol or Water at T = (313.15 and 333.15) K J. Chem. Thermodyn. 2009, 41, 11-16
86. Calvar, N.; Gonzalez, E. J.; Dominguez, A.; Macedo, E. A. Acoustic, Volumetric and Osmotic Properties of Binary Mixtures Containing the Ionic Liquid 1-Butyl-3-methylimidazolium Dicyanamide Mixed with Primary and Secondary Alcohols J. Chem. Thermodyn. 2012, 50, 19-29