Diffusion of xylene isomers in the MIL-47(V) MOF material: A synergic combination of computational and experimental tools

Journal of Physical Chemistry C

Volumn 117, Issue 12, 2013, Pages 6293-6302

  Rives, S ^a,b   Jobic, H ^b   Kolokolov, D I ^c   Gabrienko, A A ^c   Stepanov, A G ^c   Ke, Y ^a   Frick, B ^d   Devic, T ^e   Ferey G ^e   Maurin, G ^a  

^a UNIV MONTPELLIER   (France)

^b UNIVERSITÉ LYON 1   (France)

^c BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^d INSTITUT LAUE LANGEVIN   (France)

^e UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM NUCLEAR MAGNETIC RESONANCE; HIGH ACTIVATION ENERGY; HIGH-TEMPERATURE REGIME; LOW-TEMPERATURE REGIME; METAL ORGANIC FRAMEWORK; MOLECULAR DYNAMICS SIMULATIONS; QUASIELASTIC NEUTRON SCATTERING; SELF-DIFFUSION COEFFICIENTS;

ACTIVATION ENERGY; CRYSTALLINE MATERIALS; DIFFUSION; ISOMERS; MOLECULAR DYNAMICS; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

XYLENE;

EID: 84875751856     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp400507w     Document Type: Article

References (87)

1. Karayannidis, G. P.; Sideridou, I. D.; Zamboulis, D. N.; Bikiaris, D. N.; Sakalis, A. J. Thermal Behavior and Tensile Properties of Poly(ethylene terephthalate- co -ethylene isophthalate) J. Appl. Polym. Sci. 2000, 78, 200-207
2. Laurich, S. A. p-Xylene Process. US Patent 3467724, September 16, 1969.
3. Vicens, J.; Armah, A. E.; Fuji, S.; Tomita, K. I. Separation of Xylenes by Extractive Crystallization with Calixarenes J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 159-163
4. Shiau, L. D.; Wen, C. C.; Lin, B. S. Separation of p -Xylene from the Multicomponent Xylene System by Stripping Crystallization AIChE J. 2008, 54, 337-342
5. Roesler, C. M.; Kulprathipanja, S.; Rekoske, J. E. Adsorptive Separation Process for Recovery of Para-xylene. US Patent 6706938, March 16, 2004.
6. Vickers, G. H. Para-xylene and Ethylbenzene Separation from Mixed C8 Aromatics. US Patent 20040010170, January 15, 2004.
7. Leflaive, P.; Barthelet, K. Process for Separating Meta-xylene from a Feed of Aromatic Hydrocarbons by Liquid Phase Adsorption. US Patent 7468468, December 23, 2008.
8. Broughton, D. B.; Neuzil, R. W.; Pharis, J. M.; Brearley, C. S. The Parex Process for the Recovery of Paraxylene Chem. Eng. Prog. 1970, 66, 70-75
9. Minceva, M.; Gomes, P. S.; Meshko, V.; Rodrigues, A. E. Simulated Moving Bed Reactor for Isomerization and Separation of p -xylene Chem. Eng. J. 2008, 140, 305-323
10. Jin, W. H.; Wankat, P. C. Hybrid Simulated Moving Bed Processes for the Purification of p -Xylene Sep. Sci. Technol. 2007, 42, 669-700
11. Minceva, M.; Rodrigues, A. E. Influence of the Transfer Line Dead Volume on the Performance of an Industrial Scale Simulated Moving Bed for p -Xylene Separation Sep. Sci. Technol. 2003, 38, 1463-1497
12. Drechsel, B.; Haeîntsch, W.; Weber, K. Contributions for Design and Optimization of Adsorption Processes. Influence of the Adsorber Control Chem. Technol. 1991, 43, 57-60
13. Spindler, H.; Stief, C.; Haeîntsch, W.; Entner, R. The Influence of the Composition of Desorbents on a Number of Sorption Properties of the Ca-exchanged 5A Molecular Sieve in the Parex Process Chem. Technol. 1990, 42, 159-160
14. 8 Aromatics on K-Y Faujasite Ind. Eng. Chem. Res. 1991, 30, 752-760
15. + Cations J. Colloid Interface Sci. 1980, 76, 298-304
16. Daramola, M. O.; Burger, A. J.; Pera-Titus, M.; Giroir-Fendler, A.; Miachon, S. Dalmon, J. A.; Lorenzen, L. Separation and Isomerization of Xylenes using Zeolite Membranes: a Short Overview Asia-Pac. J. Chem. Eng. 2010, 5, 815-837
17. 8 Aromatics Ind. Eng. Chem. Res. 2005, 44, 5703-5714
18. Minceva, M.; Rodrigues, A. E. Adsorption of Xylenes on Faujasite-Type Zeolite: Equilibrium and Kinetics in Batch Adsorber Chem. Eng. Res. Des. 2004, 82, 667-681
19. Cottier, V.; Bellat, J.-P.; Simonot-Grange, M.-H.; Methivier, A. Adsorption of p -Xylene and m -Xylene Gas Mixtures on BaY and NaY Zeolites. Coadsorption Equilibria and Selectivities J. Phys. Chem. B 1997, 101, 4798-4802
20. Roethe, K. P.; Fiedler, K.; Roethe, A.; Suckow, M.; Stach, H.; Spindler, H.; Wittke, H.; Seidel, G.; Ermischer, W.; Roscher, W. On the Sorption Properties of Na(Ca,Mg) A Molecular Sieves Used in the Parex Process Chem. Technol. 1985, 37, 107-112
21. Gu, X. H.; Dong, J. H.; Nenoff, T. M.; Ozokwelu, D. E. Separation of p -Xylene from Multicomponent Vapor Mixtures Using Tubular MFI Zeolites Membranes J. Membr. Sci. 2006, 280, 624-633
22. 8 Aromatics on Binder-free Hydrophobic Adsorbent of MFI Zeolite. I. Studies on Static Equilibrium Microporous Mesoporous Mater. 2000, 39, 149-161
23. Mohammadi, T.; Rezaeian, M. P. Separation of Isomeric Xylenes: Experimental and Modeling Sep. Sci. Technol. 2009, 44, 817-840
24. Wu, Z. X.; Yang, Y. X.; Tu, B.; Webley, P. A.; Zhao, D. Y. Adsorption of Xylene Isomers on Ordered Hexagonal Mesoporous FDU-15 Polymer and Carbon Materials Adsorption 2009, 15, 123-132
25. 8 Aromatic Isomers by Pervaporation through Commercial Polymer Films J. Membr. Sci. 1987, 30, 111-116
26. Férey, G. Hybrid Porous Solids; Past, Present, Future Chem. Soc. Rev. 2008, 37, 191-214
27. Metal-Organic Frameworks Editorial. Chem. Rev. 2012, 112, (2)
28. Metal-Organic Frameworks Editorial. Chem. Soc. Rev. 2009, 38, 1380-1399.
29. Li, J.-R.; Sculley, J.; Zhou, H.-C. Metal-Organic Frameworks for Separations Chem. Rev. 2012, 869-932
30. Férey, G.; Serre, C.; Devic, T.; Maurin, G.; Jobic, H.; Llewellyn, P. L.; De Weireld, G.; Vimont, A.; Daturi, M.; Chang, J. S. Why Hybrid Porous Solids Capture Greenhouse Gases? Chem. Soc. Rev. 2011, 40, 550-562
31. Sumida, K.; Rogow, D. L.; Mason, J. A.; McDonald, T. M.; Bloch, E. D.; Herm, Z. R.; Bae, T. H.; Long, J. R. Carbon Dioxide Capture in Metal-Organic Frameworks Chem. Rev. 2012, 112, 724-781
32. Bloch, E. D.; Queen, W. L.; Krishna, R.; Zadrozny, J. M.; Brown, C. M.; Long, J. R. Hydrocarbons Separations in a Metal-Organic Framework with Open Iron(II) Coordination Sites Science 2012, 335, 1606-1610
33. Bae, Y. S.; Lee, C. Y.; Kim, K. C.; Farha, O. K.; Nickias, P.; Hupp, J. T.; Nguyen, S. T.; Snurr, R. Q. High Propene/Propane Selectivity in Isostructural Metal-Organic Frameworks with High Densities of Open Metal Sites Angew. Chem., Int. Ed. 2012, 51, 1857-1860
34. Yoon, J. W.; Seo, Y. K.; Hwang, Y. K.; Chang, J. S.; Leclerc, H.; Wuttke, S.; Bazin, P.; Vimont, A.; Daturi, M.; Bloch, E. Controlled Reducibility of a Metal-Organic Framework with Coordinatively Unsaturated Sites for Preferential Gas Sorption Angew. Chem., Int. Ed. 2010, 49, 5949-5952
35. Peralta, D.; Chaplais, G.; Simon-Masseron, A.; Barthelet, K.; Chizallet, C.; Quoineaud, A. A.; Pirngruber, G. D. Comparison of the Behavior of Metal-Organic Frameworks and Zeolites for Hydrocarbons Separations J. Am. Chem. Soc. 2012, 134, 8115-81126
36. Huang, L. M.; Wang, H. T.; Chen, J. X.; Wang, Z. B.; Sun, J. Y.; Zhao, D. Y.; Yan, Y. S. Synthesis, Morphology Control, and Properties of Porous Metal-Organic Coordination Polymers Microporous Mesoporous Mater. 2003, 58, 105-114
37. Gu, Z. Y.; Jiang, D. Q.; Wang, H. F.; Cui, X. Y.; Yan, X. P. Adsorption and Separation of Xylene Isomers and Ethylbenzene on Two Zn-Terephthalalte Metal-Organic Frameworks J. Phys. Chem. C 2010, 114, 311-316
38. Nicolau, M. P. M.; Barcia, P. S.; Gallegos, J. M.; Silva, J. A. C.; Rodrigues, A. E.; Chen, B. L. Single- and Multicomponent Vapor-Phase Adsorption of Xylene Isomers and Ethylbenzene in a Microporous Metal-Organic Framework J. Phys. Chem. C 2009, 113, 13173-13179
39. Gu, Z.-Y.; Yan, X.-P. Metal-Organic Framework MIL-101 for High-Resolution Gas-Chromatographic Separation of Xylene Isomers and Ethylbenzene Angew. Chem., Int. Ed. 2010, 49, 1477-1480
40. Jin, Z.; Zhao, H. Y.; Zhao, X. J.; Fang, Q. R.; Long, J. R. A; Zhu, G. S. Novel Microporous MOF with the Capability of Selective Adsorption of Xylenes Chem. Commun. 2010, 46, 8612-8614
41. Barcia, P. S.; Guimaraes, D.; Mendes, P. A. P.; Silva, J. A. C.; Guillerm, V.; Chevreau, H.; Serre, C.; Rodrigues, A. E. Reverse Shape Selectivity in the Adsorption of Hexane and Xylene Isomers in MOF UiO-66 Microporous Mesoporous Mater. 2011, 139, 67-73
42. Vermoortele, F.; Maes, M.; Moghadam, P. Z.; Lennox, M. J.; Ragon, F.; Boulhout, M.; Biswas, S.; Laurier, K. G. M.; Beurroies, I.; Denoyel, R. p- Xylene-Selective Metal-Organic Frameworks: A Case of Topology-Directed Selectivity J. Am. Chem. Soc. 2011, 133, 18526-18529
43. Moreira, M. A.; Santos, J. C.; Ferreira, A. F. P.; Loureiro, J. M.; Ragon, F.; Horcajada, P.; Shim, K. E.; Hwang, Y. K.; Lee, U. H.; Chang, J. S. Reverse Shape Selectivity in the Liquid-Phase Adsorption of Xylene Isomers in Zirconium Terephthalate MOF UiO-66 Langmuir 2012, 28, 5715-5723
44. Finsy, V.; Kirschhock, C. E. A.; Vedts, G.; Maes, M.; Alaerts, L.; De Vos, D. E.; Baron, G. V.; Denayer, J. F. M. Framework Breathing in the Vapour-Phase Adsorption and Separation of Xylene Isomers with the Metal-Organic Framework MIL-53 Chem.-Eur. J. 2009, 15, 7724-7731
45. Moreira, M. A.; Santos, J. C.; Ferreira, A. F. P.; Loureiro, J. M.; Rodrigues, A. E. Influence of the Eluent in the MIL-53(Al) Selectivity for Xylene Isomers Separation Ind. Eng. Chem. Res. 2011, 50, 7688-7695
46. Moreira, M. A.; Santos, J. C.; Ferreira, A. F. P.; Muller, U.; Trukhan, N.; Loureiro, J. M.; Rodrigues, A. E. Selective Liquid Phase Separation of ortho-Xylene with the Microporous MIL-53(Al) Sep. Sci. Technol. 2011, 46, 1995-2003
47. El Osta, R.; Carlin-Sinclair, A.; Guillou, N.; Walton, R. I.; Vermoortele, F.; Maes, M.; de Vos, D.; Millange, F. Liquid-Phase Adsorption and Separation of Xylene Isomers by the Flexible Porous Metal-Organic Framework MIL-53(Fe) Chem. Mater. 2012, 24, 2781-2791
48. Alaerts, L.; Kirschhock, C. E. A.; Maes, M.; van der Veen, M. A.; Finsy, V.; Depla, A.; Martens, J. A.; Baron, G. V.; Jacobs, P. A.; Denayer, J. E. M. Selective Adsorption and Separation of Xylene Isomers and Ethylbenzene with the Porous Vanadium(IV) Terephthalate MIL-47 Angew. Chem., Int. Ed. 2007, 46, 4293-4297
49. Finsy, V.; Verelst, H.; Alaerts, L.; De Vos, D.; Jacobs, P. A.; Baron, G. V.; Denayer, J. F. M. Pore-Filling-Dependent Selectivity Effects in the Vapor-Phase Separation of Xylene Isomers on the Metal-Organic Framework MIL-47 J. Am. Chem. Soc. 2008, 130, 7110-7118
50. Maes, M.; Vermoortele, F.; Boulhout, M.; Boudewijns, T.; Kirschhock, C.; Ameloot, R.; Beurroies, I.; Denoyel, R.; De Vos, D. E. Enthalpic Effects in the Adsorption of Alkylaromatics in the Metal-Organic Frameworks MIL-47 and MIL-53 Microporous Mesoporous Mater. 2012, 157, 82-88
51. Castillo, J. M.; Vlugt, T. J. H.; Calero, S. Molecular Simulation Study on the Separation of Xylene Isomers in MIL-47 Metal-Organic Frameworks J. Phys. Chem. C 2009, 113, 20869-20874
52. Ghysels, A.; Vandichel, M.; Verstraelen, T.; van der Veen, M. A.; De Vos, D. E.; Waroquier, M.; Van Speybroeck, V. Host-Guest and Guest-Guest Interactions between Xylene Isomers Confined in the MIL-47(V) Pore System Theor. Chem. Acc. 2012, 1234-1246
53. 2 Diffusion in Metal Organic Framework Materials Phys. Rev. Lett. 2008, 245901.1-245901.4
54. 2 in the MOF Type Systems MIL-47(V) and MIL-53(Cr): A Combination of Microcalorimetry and QENS Experiments with Molecular Simulations J. Phys. Chem. C 2009, 113, 7802-7812
55. 2 in the Metal-Organic Framework MIL-47(V) Explored by Quasi-Elastic Neutron Scattering Experiments and Molecular Dynamics Simulations ACS Nano 2010, 4, 143-152
56. Kolokolov, D. I.; Jobic, H.; Stepanov, A. G.; Ollivier, J.; Rives, S.; Maurin, G.; Devic, T.; Serre, C.; Ferey, G. Experimental and Simulation Evidence of a Corkscrew Motion for Benzene in the Metal-Organic Framework MIL-47 J. Phys. Chem. C 2012, 116, 15093-15098
57. Rosenbach, N.; Jobic, H.; Ghoufi, A.; Salles, F.; Maurin, G.; Bourrelly, S.; Llewellyn, P. L.; Devic, T.; Serre, C.; Férey, G. Quasi-Elastic Neutron Scattering and Molecular Dynamics Study of Methane Diffusion in Metal-Organic Frameworks MIL-47(V) and MIL-53(Cr) Angew. Chem., Int. Ed. 2008, 47, 6611-6615
58. Jobic, H.; Rosenbach, N.; Ghoufi, A.; Kolokolov, D. I.; Yot, P. G.; Devic, T.; Serre, C.; Férey, G.; Maurin, G. Unusual Chain-Length Dependence of the Diffusion of n -Alkanes in the Metal-Organic Framework MIL-47(V): The Blowgun Effect Chem.-Eur. J. 2010, 16, 10337-10341
59. Rives, S.; Jobic, H.; Ragon, F.; Devic, T.; Serre, C.; Ferey, G.; Ollivier, J.; Maurin, G. Diffusion of Long Chain n -Alkanes in the Metal-Organic Framework MIL-47(V): A Combination of Neutron Scattering Experiments and Molecular Dynamics Simulations Microporous Mesoporous Mater. 2012, 164, 259-265
60. 2 in the Highly Flexible Metal-Organic Framework MIL-53(Cr) Angew. Chem., Int. Ed. 2009, 48, 8335-8339
61. Salles, F.; Bourrelly, S.; Jobic, H.; Devic, T.; Guillerm, V.; Llewellyn, P.; Serre, C.; Ferey, G.; Maurin, G. Molecular Insight into the Adsorption and Diffusion of Water in the Versatile Hydrophilic/Hydrophobic Flexible MIL-53(Cr) MOF J. Phys. Chem. C 2011, 115, 10764-10776
62. 4 Gas Mixture within the Porous Zirconium Terephthalate UiO-66(Zr): A Joint Experimental and Modeling Approach J. Phys. Chem. C 2011, 115, 13768-13774
63. 2 and CH4 within the Porous Zirconium Terephthalate UiO-66(Zr) Chem.-Eur. J. 2011, 17, 8882-8889
64. Mizuno, M.; Itakura, N.; Endo, K. Effects of Strong Paramagnetic Interactions on Solid-State Deuterium NMR Spectra Chem. Phys. Lett. 2005, 416, 358-363
65. Barthelet, K.; Marrot, J.; Riou, D.; Ferey, G. A Breathing Hybrid Organic-Inorganic Solid with Very Large Pores and High Magnetic Characteristics Angew. Chem., Int. Ed. 2001, 41, 281-284
66. 2H NMR Using the Quadrupole-Echo Experiment J. Magn. Reson. 2003, 164, 343-350
67. Trung, T. K.; Deroche, I.; Rivera, A.; Yang, Q. Y.; Yot, P.; Ramsahye, N.; Vinot, S. D.; Devic, T.; Horcajada, P.; Serre, C. Hydrocarbon Adsorption in the Isostructural Metal-Organic Frameworks MIL-53(Cr) and MIL-47(V) Microporous Mesoporous Mater. 2011, 140, 114-119
68. 2H NMR Spectroscopy Angew. Chem., Int. Ed. 2010, 49, 4791-4794
69. Yot, P. G.; Ma, Q. T.; Haines, J.; Yang, Q. Y.; Ghoufi, A.; Devic, T.; Serre, C.; Dmitriev, V.; Férey, G.; Zhong, C. L. Large Breathing of the MOF MIL-47(V) under Mechanical Pressure: a Joint Experimental-Modeling Exploration Chem. Sci. 2012, 3, 1100-1104
70. 2 adsorption in the MIL-53(Al) System Phys. Chem. Chem. Phys. 2007, 9, 1059-1063
71. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. UFF, a Full Periodic Table Force Field for Molecular Mechanics and Molecular Dynamics Simulations J. Am. Chem. Soc. 1992, 114, 10024-10035
72. Mayo, S. L.; Olafson, B. D.; Goddard, W. A. DREIDING: a Generic Force Field for Molecular Simulations J. Phys. Chem. 1990, 94, 8897-8909
73. Rai, N.; Siepmann, J. I. Transferable Potentials for Phase Equilibria. 9. Explicit Hydrogen Description of Benzene and Five-Membered and Six-Membered Heterocyclic Aromatic Compounds J. Phys. Chem. B 2007, 111, 10790-10799
74. Wick, C. D.; Martin, M. G.; Siepmann, J. I. Transferable Potentials for Phase Equilibria. 4. United-Atom Description of Linear and Branched Alkenes and of Alkylbenzenes J. Phys. Chem. B 2000, 104, 8008-8016
75. Oie, T.; Maggiora, G. M.; Christoffersen, R. E.; Duchamp, D. J. Development of a Flexible Intra- and Intermolecular Empirical Potential Function for Large Molecular Systems Int. J. Quantum Chem. 1981, 20, 1-47
76. Smith, W.; Forester, T. R. DL-POLY-2.0: A General-Purpose Parallell Molecular Dynamics Simulation Package J. Mol. Graphics 1996, 14, 136-141
77. Frenkel, D.; Smit, B. Understanding Molecular Simulation; Academic Press: New York, 1996.
78. Beerdsen, E.; Smit, B.; Dubbeldam, D. Molecular Simulation of Loading Dependent Slow Diffusion in Confined Systems Phys. Rev. Lett. 2004, 93, 248301.1-248301.4
79. Jobic, H.; Bée, M.; Méthivier, A.; Combet, J. Influence of the Cation Composition on the Dynamics of Xylenes in X-type Zeolites Microporous Mesoporous Mater. 2001, 42, 135-155
80. Zhai, D.; Zhao, L.; Gao, J. S.; Xu, C. M. Effect of Temperature on the Diffusion Mechanism of Xylene Isomers in a FAU zeolite: a Molecular Dynamics Study Phys. Chem. Chem. Phys. 2012, 14, 7296-7303
81. Takakura, K.; Ueda, T.; Miyakubo, K.; Eguchi, T. Local Structure and Dynamics of Benzene Confined in the IRMOF-1 Nanocavity as Studied by Molecular Dynamics Simulation Phys. Chem. Chem. Phys. 2013, 15, 279-290
82. Krishna, R.; Li, S.; van Baten, J. M.; Falconer, J. L.; Noble, R. D. Investigation of Slowing-down and Speeding-up Effects in Binary Mixture Permeation across SAPO-34 and MFI Membranes Sep. Purif. Technol. 2008, 60, 230-236
83. Krishna, R. Diffusion in Porous Crystalline Materials Chem. Soc. Rev. 2012, 41, 3099-3118
84. Jelinski, L. W. In High Resolution NMR Spectroscopy of Synthetic Polymers in Bulk (Methods and Stereochemical Analysis); Komoroski, R. A., Ed.; VCH Publishers: New York, 1986; Vol. 7, p 335.
85. Geil, B.; Isfort, O.; Boddenberg, B.; Favre, D. E.; Chmelka, B. F.; Fujara, F. Reorientational and Translational Dynamics of Benzene in Zeolite NaY as Studied by One- and Two-Dimensional Exchange Spectroscopy and Static-Field-Gradient Nuclear Magnetic Resonance J. Chem. Phys. 2002, 116, 2184-2193
86. Spiess, H. W. In NMR Basic Principles and Progress; Diehl, P.; Fluck, E.; Kosfeld, R., Eds.; Springer-Verlag: New York, 1978; Vol. 15, p 55.
87. Macho, V.; Brombacher, L.; Spiess, H. W. The NMR-WEBLAB: An Internet Approach to NMR Lineshape Analysis Appl. Magn. Reson. 2001, 20, 405-432