Synthesis of submicrometer-sized Sn-MCM-41 particles and their catalytic performance in Baeyer-Villiger oxidation

Abstract

Submicrometer-sized tin-containing MCM-41 particles with a size of several hundred nanometers(Sn-MCM-41/SMPs) were rapidly prepared with tin chloride as tin source and tetraethyl orthosilicate as silicon source via a dilute solution route in sodium hydroxide medium at room temperature. The characterization results show the highly ordered hexagonal mesopores and tetrahedral Sn species in Sn-MCM-41/SMPs. The material proved to be active and selective for Baeyer-Villiger oxidation of adamantanone with aqueous H₂O₂. Notably, Sn-MCM-41/SMPs displayed a higher initial reaction rate and turnover number(TON) than common micrometer-sized Sn-MCM-41 large particles(Sn-MCM-41/LPs), mainly attributed to the accelerated diffusion of the reactants and enhanced accessibility to the catalytic Sn species via shorter mesopore channels in Sn-MCM-41/SMPs. Furthermore, Sn-MCM-41/SMPs could be reused without the loss of activity after five runs, indicating that Sn active sites in the submicrometer-sized particles are remarkably stable. The study shows that decreasing particle size of Sn-MCM-41 in submicrometer scale is an effective way to achieve catalysts for Baeyer-Villiger oxidations with improved catalytic performance.

Keywords

Sn-MCM-41 / Submicrometer-sized particles / Shorter mesopore channel / Baeyer-Villiger oxidation

References

[1] Strukul G. Angew. Chem. Int. Ed., 1998, 37: 1198.

[2] ten Brink G J, Arends I W C E, Sheldon R A. Chem. Rev., 2004, 104: 4105.

[3] Jiménez-Sanchidrían C, Ruiz J R. Tetrahedron, 2008, 64: 2011.

[4] Renz M, Meunier B. Eur. J. Org. Chem., 1999, 737.

[5] Michelin R A, Sgarbossa P, Scarso A, Strukul G. Coord. Chem. Rev., 2010, 254: 646.

[6] Corma A, Nemeth L T, Renz M, Valencia S. Nature, 2001, 412: 423.

[7] Corma A, Navarro M T, Nemeth LT, Renz M. Chem. Commun., 2001, 2190.

[8] Renz M, Blasco T, Corma A, Fornés V, Jensen R, Nemeth L. Chem. Eur. J., 2002, 8: 4708.

[9] Llamas R, Jiménez-Sanchidrián C, Ruiz J R. Appl. Catal. B, 2007, 72: 18.

[10] Pillai U R, Sahle-Demessie E. J. Mol. Catal. A, 2003, 191: 93.

[11] Fischer J, Hölderich W F. Appl. Catal. A, 1999, 180: 435.

[12] Hara T, Hatakeyama M, Kim A, Ichikuni N, Shimazu S. Green Chem., 2012, 14: 771.

[13] Corma A, Navarro M T, Renz M. J. Catal., 2003, 219: 242.

[14] Pachamuthu M P, Shanthi K, Luque R, Ramanathan A. Green Chem., 2013, 15: 2158.

[15] Selvaraj M, Sinhab P K. New J. Chem., 2010, 34: 1921.

[16] Gaydhankar T R, Joshi P N, Kalita P, Kumar R. J. Mol. Catal. A, 2007, 265: 306.

[17] de Cremer G, Roeffaers M B J, Bartholomeeusen E, Lin K, Dedecker P, Pescarmona P P, Jacobs P A, de Vos D E, Hofkens J, Sels B F. Angew. Chem. Int. Ed., 2010, 49: 908.

[18] Lin K, Pescarmona P P, Houthoofd K, Liang D, van Tendeloo G, Jacobs P A. J. Catal., 2009, 263: 75.

[19] Jiang Y, Lin K, Zhang Y, Liu J, Li G, Sun J, Xu X. Appl. Catal. A, 2012, 445/446: 172.

[20] Cai Q, Luo Z S, Pang W Q, Fan Y W, Chen X H, Cui F Z. Chem. Mater., 2001, 13: 258.

[21] Cao Y Y, Wang Y Q, Hao J K. Chem. J. Chinese Universities, 2011, 32(5): 1138.

[22] Sadasivan S, Fowler C E, Khushalani D, Mann S. Angew. Chem. Int. Ed., 2002, 41: 2151.

[23] Taralkar U S, Kalita P, Kumar R, Joshi P N. Appl. Catal. A, 2009, 358: 88.

[24] Niphadkar P S, Garade A C, Jha R K, Rode C V, Joshi P N. Mccropor. Mesopor. Mater., 2010, 136: 115.

[25] Ramaswamy V, Shah P, Lazar K, Ramaswamy A V. Catal. Surv. Asia, 2008, 12: 283.

[26] Chaudhari K, Das T K, Rajmohanan P R, Lazar K, Sivasanker S, Chandwadkar A J. J. Catal., 1999, 183: 281.