Mechanistic studies of aldol condensations in UiO-66 and UiO-66-NH2 metal organic frameworks

Journal of Catalysis

Volumn 331, Issue , 2015, Pages 1-12

  Hajek, Julianna ^a   Vandichel, Matthias ^a   Van De Voorde, Ben ^b   Bueken, Bart ^b   De Vos, Dirk ^b   Waroquier, Michel ^a   Van Speybroeck, Veronique ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Aldol condensation; First principle kinetics; Heterogeneous catalysis; Jasminaldehyde; UiO 66; UiO 66 NH2

Indexed keywords

CATALYSIS; CATALYSTS; CONDENSATION; CRYSTALLINE MATERIALS; DENSITY FUNCTIONAL THEORY; FREE ENERGY; KETONES; ORGANOMETALLICS;

ALDOL CONDENSATION; FIRST PRINCIPLES; JASMINALDEHYDE; UIO-66; UIO-66-NH2;

CONDENSATION REACTIONS;

EID: 84940513033     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2015.08.015     Document Type: Article

References (63)

1. M.J. Climent, A. Corma, V. Fornes, R. Guil-Lopez, and S. Iborra Aldol condensations on solid catalysts: a cooperative effect between weak acid and base sites Adv. Synth. Catal. 344 2002 1090 1096
2. M.J. Climent, A. Corma, R. Guil-Lopez, S. Iborra, and J. Primo Use of mesoporous MCM-41 aluminosilicates as catalysts in the preparation of fine chemicals - a new route for the preparation of Jasminaldehyde with high selectivity J. Catal. 175 1998 70 79
3. S.K. Sharma, P.A. Parikh, and R.V. Jasra Eco-friendly synthesis of jasminaldehyde by condensation of 1-heptanal with benzaldehyde using hydrotalcite as a solid base catalyst J. Mol. Catal. A - Chem. 286 2008 55 62
4. M.J. Climent, A. Corma, H. Garcia, R. Guil-Lopez, S. Iborra, and V. Fornes Acid-base bifunctional catalysts for the preparation of fine chemicals: synthesis of jasminaldehyde J. Catal. 197 2001 385 393
5. S.K. Sharma, H.A. Patel, and R.V. Jasra Synthesis of jasminaldehyde using magnesium organo silicate as a solid base catalyst J. Mol. Catal. A - Chem. 280 2008 61 67
6. F. Vermoortele, R. Ameloot, A. Vimont, C. Serre, and D. De Vos An amino-modified Zr-terephthalate metal-organic framework as an acid-base catalyst for cross-aldol condensation Chem. Commun. 47 2011 1521 1523
7. G. Ferey Hybrid porous solids: past, present, future Chem. Soc. Rev. 37 2008 191 214
8. J.L.C. Rowsell, and O.M. Yaghi Metal-organic frameworks: a new class of porous materials Micropor. Mesopor. Mater. 73 2004 3 14
9. O.M. Yaghi, M. O'Keeffe, N.W. Ockwig, H.K. Chae, M. Eddaoudi, and J. Kim Reticular synthesis and the design of new materials Nature 423 2003 705 714
10. B. Van de Voorde, B. Bueken, J. Denayer, and D. De Vos Adsorptive separation on metal-organic frameworks in the liquid phase Chem. Soc. Rev. 43 2014 5766 5788
11. M. Kim, and S.M. Cohen Discovery, development, and functionalization of Zr(IV)-based metal-organic frameworks CrystEngComm 14 2012 4096 4104
12. P. Valvekens, F. Vermoortele, and D. De Vos Metal-organic frameworks as catalysts: the role of metal active sites Catal. Sci. Technol. 3 2013 1435 1445
13. D. Farrusseng, S. Aguado, and C. Pinel Metal-organic frameworks: opportunities for catalysis Angew. Chem. Int. Ed. 48 2009 7502 7513
14. J. Lee, O.K. Farha, J. Roberts, K.A. Scheidt, S.T. Nguyen, and J.T. Hupp Metal-organic framework materials as catalysts Chem. Soc. Rev. 38 2009 1450 1459
15. A. Dhakshinamoorthy, M. Alvaro, and H. Garcia Metal-organic frameworks as heterogeneous catalysts for oxidation reactions Catal. Sci. Technol. 1 2011 856 867
16. L.Q. Ma, C. Abney, and W.B. Lin Enantioselective catalysis with homochiral metal-organic frameworks Chem. Soc. Rev. 38 2009 1248 1256
17. A. Dhakshinamoorthy, M. Alvaro, and H. Garcia Commercial metal-organic frameworks as heterogeneous catalysts Chem. Commun. 48 2012 11275 11288
18. A. Corma, H. Garcia, and F.X.L.I. Xamena Engineering metal organic frameworks for heterogeneous catalysis Chem. Rev. 110 2010 4606 4655
19. J.H. Cavka, S. Jakobsen, U. Olsbye, N. Guillou, C. Lamberti, S. Bordiga, and K.P. Lillerud A new zirconium inorganic building brick forming metal organic frameworks with exceptional stability J. Am. Chem. Soc. 130 2008 13850 13851
20. V. Guillerm, S. Gross, C. Serre, T. Devic, M. Bauer, and G. Ferey A zirconium methacrylate oxocluster as precursor for the low-temperature synthesis of porous zirconium(IV) dicarboxylates Chem. Commun. 46 2010 767 769
21. M. Kandiah, M.H. Nilsen, S. Usseglio, S. Jakobsen, U. Olsbye, M. Tilset, C. Larabi, E.A. Quadrelli, F. Bonino, and K.P. Lillerud Synthesis and stability of tagged UiO-66 Zr-MOFs Chem. Mater. 22 2010 6632 6640
22. L. Valenzano, B. Civalleri, S. Chavan, S. Bordiga, M.H. Nilsen, S. Jakobsen, K.P. Lillerud, and C. Lamberti Disclosing the complex structure of UiO-66 metal organic framework: a synergic combination of experiment and theory Chem. Mater. 23 2011 1700 1718
23. F. Vermoortele, M. Vandichel, B. Van de Voorde, R. Ameloot, M. Waroquier, V. Van Speybroeck, and D.E. De Vos Electronic effects of linker substitution on lewis acid catalysis with metal-organic frameworks Angew. Chem. Int. Ed. 51 2012 4887 4890
24. M. Vandichel, J. Hajek, F. Vermoortele, D.E. De Vos, M. Waroquier, and V. Van Speybroeck Active site engineering of UiO-66 type metal-organic frameworks by intentional creation of defects: a theoretical rationalization CrystEngComm 17 2015 395 406
25. Q.Y. Yang, A.D. Wiersum, P.L. Llewellyn, V. Guillerm, C. Serred, and G. Maurin Functionalizing porous zirconium terephthalate UiO-66(Zr) for natural gas upgrading: a computational exploration Chem. Commun. 47 2011 9603 9605
26. M. Kandiah, S. Usseglio, S. Svelle, U. Olsbye, K.P. Lillerud, and M. Tilset Post-synthetic modification of the metal-organic framework compound UiO-66 J. Mater. Chem. 20 2010 9848 9851
27. G.E. Cmarik, M. Kim, S.M. Cohen, and K.S. Walton Tuning the adsorption properties of UiO-66 via ligand functionalization Langmuir 28 2012 15606 15613
28. S.M. Chavan, G.C. Shearer, S. Svelle, U. Olsbye, F. Bonino, J. Ethiraj, K.P. Lillerud, and S. Bordiga Synthesis and characterization of amine-functionalized mixed-ligand metal-organic frameworks of UiO-66 topology Inorg. Chem. 53 2014 9509 9515
29. 2 ChemCatChem 4 2012 1725 1728
30. M.N. Timofeeva, V.N. Panchenko, J.W. Jun, Z. Hasan, M.M. Matrosova, and S.H. Jhung Effects of linker substitution on catalytic properties of porous zirconium terephthalate UiO-66 in acetalization of benzaldehyde with methanol Appl. Catal. A - Gen. 471 2014 91 97
31. Y. Yang, H.F. Yao, F.G. Xi, and E.Q. Gao Amino-functionalized Zr(IV) metal-organic framework as bifunctional acid-base catalyst for Knoevenagel condensation J. Mol. Catal. A - Chem. 390 2014 198 205
32. R. Kardanpour, S. Tangestaninejad, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork, A.R. Khosropour, and F. Zadehahmadi Highly dispersed palladium nanoparticles supported on amino functionalized metal-organic frameworks as an efficient and reusable catalyst for Suzuki cross-coupling reaction J. Organomet. Chem. 761 2014 127 133
33. J. Zhu, P.C. Wang, and M. Lu Selective oxidation of benzyl alcohol under solvent-free condition with gold nanoparticles encapsulated in metal-organic framework Appl. Catal. A - Gen. 477 2014 125 131
34. Y.M. Chung, H.Y. Kim, and W.S. Ahn Friedel-Crafts acylation of p-xylene over sulfonated zirconium terephthalates Catal. Lett. 144 2014 817 824
35. Z.Y. Guo, C.X. Xiao, R.V. Maligal-Ganesh, L. Zhou, T.W. Goh, X.L. Li, D. Tesfagaber, A. Thiel, and W.Y. Huang Pt nanoclusters confined within metal organic framework cavities for chemoselective cinnamaldehyde hydrogenation ACS Catal. 4 2014 1340 1348
36. K. Leus, M. Vandichel, Y.Y. Liu, I. Muylaert, J. Musschoot, S. Pyl, H. Vrielinck, F. Callens, G.B. Marin, C. Detavernier, P.V. Wiper, Y.Z. Khimyak, M. Waroquier, V. Van Speybroeck, and P. Van der Voort The coordinatively saturated vanadium MIL-47 as a low leaching heterogeneous catalyst in the oxidation of cyclohexene J. Catal. 285 2012 196 207
37. M. Vandichel, F. Vermoortele, S. Cottenie, D.E. De Vos, M. Waroquier, and V. Van Speybroeck Insight in the activity and diastereoselectivity of various Lewis acid catalysts for the citronellal cyclization J. Catal. 305 2013 118 129
38. T. Verstraelen, V. Van Speybroeck, and M. Waroquier ZEOBUILDER: a GUI toolkit for the construction of complex molecular structures on the nanoscale with building blocks J. Chem. Inf. Model. 48 2008 1530 1541
39. M. Vandichel, S. Biswas, K. Leus, J. Paier, J. Sauer, T. Verstraelen, P. Van Der Voort, M. Waroquier, and V. Van Speybroeck Catalytic performance of vanadium MIL-47 and linker-substituted variants in the oxidation of cyclohexene: a combined theoretical and experimental approach ChemPlusChem 79 2014 1183 1197
40. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision D.01 2009 Gaussian Inc. Wallingford, CT
41. P.J. Hay, and W.R. Wadt Abinitio effective core potentials for molecular calculations - potentials for the transition-metal atoms Sc to Hg J. Chem. Phys. 82 1985 270 283
42. P.J. Hay, and W.R. Wadt Abinitio effective core potentials for molecular calculations - potentials for K to Au including the outermost core orbitals J. Chem. Phys. 82 1985 299 310
43. W.R. Wadt, and P.J. Hay Abinitio effective core potentials for molecular calculations - potentials for main group elements Na to Bi J. Chem. Phys. 82 1985 284 298
44. S. Grimme, J. Antony, S. Ehrlich, and H. Krieg A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu J. Chem. Phys. 132 2010
45. G. Kresse, and J. Hafner Abinitio molecular-dynamics for liquid-metals Phys. Rev. B 47 1993 558 561
46. G. Kresse, and J. Hafner Ab-initio molecular-dynamics simulation of the liquid-metal amorphous-semiconductor transition in germanium Phys. Rev. B 49 1994 14251 14269
47. G. Kresse, and J. Furthmuller Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Comput. Mater. Sci. 6 1996 15 50
48. G. Kresse, and J. Furthmuller Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Phys. Rev. B 54 1996 11169 11186
49. S. Grimme, S. Ehrlich, and L. Goerigk Effect of the damping function in dispersion corrected density functional theory J. Comput. Chem. 32 2011 1456 1465
50. G. Kresse, and D. Joubert From ultrasoft pseudopotentials to the projector augmented-wave method Phys. Rev. B 59 1999 1758 1775
51. P.E. Blochl Projector augmented-wave method Phys. Rev. B 50 1994 17953 17979
52. V. Van Speybroeck, K. De Wispelaere, J. Van der Mynsbrugge, M. Vandichel, K. Hemelsoet, and M. Waroquier First principle chemical kinetics in zeolites: the methanol-to-olefin process as a case study Chem. Soc. Rev. 43 2014 7326 7357
53. B.A. De Moor, A. Ghysels, M.F. Reyniers, V. Van Speybroeck, M. Waroquier, and G.B. Marin Normal mode analysis in zeolites: toward an efficient calculation of adsorption entropies J. Chem. Theory Comput. 7 2011 1090 1101
54. A. Ghysels, D. Van Neck, and M. Waroquier Cartesian formulation of the mobile block Hessian approach to vibrational analysis in partially optimized systems J. Chem. Phys. 127 2007
55. M.T. Reetz, A. Meiswinkel, G. Mehler, K. Angermund, M. Graf, W. Thiel, R. Mynott, and D.G. Blackmond Why are BINOL-based monophosphites such efficient ligands in Rh-catalyzed asymmetric olefin hydrogenation? J. Am. Chem. Soc. 127 2005 10305 10313
56. P.J. Donoghue, P. Helquist, P.O. Norrby, and O. Wiest Development of a Q2MM force field for the asymmetric rhodium catalyzed hydrogenation of enamides J. Chem. Theory Comput. 4 2008 1313 1323
57. A. Ghysels, T. Verstraelen, K. Hemelsoet, M. Waroquier, and V. Van Speybroeck TAMkin: a versatile package for vibrational analysis and chemical kinetics J. Chem. Inf. Model. 50 2010 1736 1750
58. F. Vermoortele, B. Bueken, G. Le Bars, B. Van de Voorde, M. Vandichel, K. Houthoofd, A. Vimont, M. Daturi, M. Waroquier, V. Van Speybroeck, C. Kirschhock, and D.E. De Vos Synthesis modulation as a tool to increase the catalytic activity of metal-organic frameworks: the unique case of UiO-66(Zr) J. Am. Chem. Soc. 135 2013 11465 11468
59. J. Gascon, U. Aktay, M.D. Hernandez-Alonso, G.P.M. van Klink, and F. Kapteijn Amino-based metal-organic frameworks as stable, highly active basic catalysts J. Catal. 261 2009 75 87
60. J.D. Bass, A. Solovyov, A.J. Pascall, and A. Katz Acid-base bifunctional and dielectric outer-sphere effects in heterogeneous catalysis: a comparative investigation of model primary amine catalysts J. Am. Chem. Soc. 128 2006 3737 3747
61. M. Hartmann, and M. Fischer Amino-functionalized basic catalysts with MIL-101 structure Micropor. Mesopor. Mater. 164 2012 38 43
62. R. Cortese, and D. Duca A DFT study of IRMOF-3 catalysed Knoevenagel condensation Phys. Chem. Chem. Phys. 13 2011 15995 16004
63. V.N. Panchenko, M.M. Matrosova, J. Jeon, J.W. Jun, M.N. Timofeeva, and S.H. Jhung Catalytic behavior of metal-organic frameworks in the Knoevenagel condensation reaction J. Catal. 316 2014 251 259