Nanosized mesoporous composite PW12-APTES@KIT-6: An efficient heterogeneous catalyst for selective oxidation of sulfides to sulfoxides and sulfones

Authors

1 Department of Chemistry, Shahreza Branch, Islamic Azad University, 86145-311, Iran.

2 Department of Chemistry, Mobarakeh Branch, Islamic Azad University, 84815-119, Iran.

Abstract

Surface of mesostructured silica, KIT-6, was modified by grafting 3-aminopropyl-triethoxysilane (APTES) to have the positive charge, and thus, to provide sites for the immobilization of H3PW12O40 (PW12).  This modified-nanosized mesoporous silica (PW12-APTES@ KIT-6) was characterized by FTIR, XRD, BET and TEM. The oxidation of sulfides occurs effectively and selectively with H2O2 as the oxidant. PW12-APTES@KIT-6 was used as the catalyst.  The catalyst can be reused for several times but it will be less active.

Keywords


[1] A.Taguchi, F. Schuth. Microporous Mesoporous Mater. 77 (2005) 1-45.
[2] T. Tsoncheva, J. Rosenholm, C. V. Teixeira, M. Dimitrov, M. Linden, C. Minchev, Microporous Mesoporous Mater. 89 (2006) 209-218.
[3] T. Tsoncheva, J. Rosenholm, M. Linden, L. Ivanova, C. Minchev, Appl. Catal. A: Gen. 318 (2007) 234-243.
[4] T. Tsoncheva, Tz. Venkov, M. Dimitrov, C. Minchev, K. Hadjiivanov, J. Mol. Catal. A: Chem. 209 (2003) 125-134.
[5] R. Kohn, D. Paneva, M. Dimitrov, T. Tsoncheva, I. Mitov, C. Minchev, M. Froba, Microporous Mesoporous Mater. 63 (2003) 125-137.
[6] S. Forster, Top. Cur. Chem. 226 (2003) 1-28.
[7] P. L. Ravikovitch, A. V. Neimark, J. Phys. Chem. B. 105 (2001) 6817-6823.
[8] M. Choi, W. Heo, F. Kletiz, R. Ryoo, Chem. Commun. (2003) 1340-1341.
[9] F. Kletiz, S. H. Choi, r. Ryoo. Chem. Commun. (2003) 2136-2137.
[10] F. Kletiz, T. W. Kim, R. Ryoo, Langmuir 22 (2006) 440-445.
[11] I.V. Kozhevnikov, Catalysis by Polyoxometalates, Wiley, England, 2002.
[12] R. Fazaeli, S. Tangestaninejad, H. Aliyan, M. Moghadam, Appl. Catal. A: Gen. 309 (2006) 44-51.
[13] R. Fazaeli, S. Tangestaninejad, H. Aliyan Appl. Catal. A: Gen. 318 (2007) 218-226.
[14] R. Fazaeli, H. Aliyan, Appl. Catal. A: Gen. 331 (2007) 78-83.
[15] R. Fazaeli, H. Aliyan, Appl. Catal. A: Gen. 353 (2009) 74-79.
[16] The Synthesis of Sulphones, Sulphoxides, and Cyclic Sulphides; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1994.
[17] Clark, E. In Kirk–Othmer Encyclopedia of Chemical Technology, 4th ed; Kroschwitz, J. I., Howe-Grant, M., Eds.; Wiley: New York, 1997; Vol. 23, pp 134–146.
[18] X. Shi, X. Han, W. Ma, J. Wei, J. Li, Q. Zhang, Z. Chen, J. Mol. Catal. A: Chem. 341 (2011) 57–62.
[19] P. Ballistreri, F.G. Fortuna, C. Pappalardo, A.A. Tomaselli, G.M. Toscano, R. J. Mol. Catal. A: Chem. 308 (2009) 56–60.
[20] N. Gharah, S.K. Chakraborty, A. Mukherjee, R. Bhattacharyya, Inorg. Chim. Acta 362 (2009) 1089–1100.
[21] I. Sheikhshoaie, A. Rezaeifard, N. Monadi, S. Kaafi, Polyhedron 28 (2009) 733–738
[22] H. Egami, T. Katsuki. J. Am. Chem. Soc. 129 (2007) 8940-8941.
[23] F. Kleitz, S.H. Choi, R. Ryoo, Chem. Commun. (2003) 2136–2137.
[24] T.W. Kim, F. Kleitz, B. Paul, R. Ryoo, J. Am. Chem. Soc. 127 (2005) 7601–7610.
[25] V.D. Chaube, S. Shylesh, A.P. Singh, J. Mol. Catal: A: Chem. 241 (2005) 79–87.
[26] I. Diaz, C. Marquez-Alvarez, F. Mahino, J. Perez-Periente, E. Sastre, J. Catal. 193 (2000) 283–294.
[27] B.H. Wouters, T. Chen, M. Dewilde, P.J. Grobet, Micropor. Mesopor. Mater. 44–45 (2001) 453–457.
[28] A.B. Jarze˛bski, K. Szymanska, J. Bryjak, J. Mrowiec-Białon, Catal. Today 124 (2007) 2–10.
 
[29] J. Aburto, M. Ayala, I. Bustos-Jaimes, C. Montiel, E. Terres, J.M. Domınguez, E. Torres, Micropor. Mesopor. Mater. 83 (2005) 193–200.
[30] I.V. Kozhevnikov, Catalysis by Polyoxometalates, Wiley, England, 2002.
[31] V.D. Chaube, S. Shylesh, A.P. Singh, J. Mol. Catal. A: Chem. 241 (2005) 79–87.
[32] A. Prabhu, L. Kumaresan, M. Palanichamy, V. Murugesan, Appl. Catal. A: Chem. 360 (2009) 59-65.
[33] K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, Pure Appl. Chem. 57 (1985) 603-619.
[34] J.S. Beck, J.C.Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt. J. Am. Chem. Soc. 114 (1992) 10834-10843.
[35] C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck. Nature 359 (1992) 710-712.
[36] M. Che, J.C. Védrine, Characterization of solid materials and heterogeneous catalysts: From structure to surface reactivity" Wiley-VCH April 2012, 853-879.
[37] T. Tsoncheva, L. Ivanova, J. Rosenholm, M. Linden, Appl. Catal. B: Env. 89 (2009) 365-374.
[38] D. G. Castner, Ph. R. Watson, I. Y. Chan, J. Phys. Chem. 93 (1989) 3188-3194.
[39] N. Iranpoor, H. Firouzabadi, A.R. Pourali, Synlett (2004) 347-349.
[40] M.M. Lakouraj, M. Tajbakhsh, H. Tashakkorian, Lett. Org. Chem. 4 (2007) 75-79.
[41] R. Das, D. Chakraborty, Tetraheron Lett. 51 (2010) 6255-6258.
[42] Y. K. Hwang, D.-Y. Hong, J.-S. Chang, H. Seo, M. Yoon, J. Kim, S. H. Jhung, C. Serre, G. Fe´rey, Appl. Catal. A: Gen. 358 (2009) 249–253.
[43] Y. Yuan, Y. Bian, Tetrahedron Lett. 48 (2007) 8518-8520.
[44] S.V. Suresh, K. Rajesh, D.C. Babu, N. Suryakiran, Y. Venkateswarlu, Tetrahedron Lett. 49 (2008) 3463-3465.
[45] S. Kumar, S. Verma, S.L. Jain, B. Sain, Tetrahedron Lett. 52 (2011) 3393-3396.
[46] A. G. Sathicq, G. P. Romanelli, V. Palermo, P. G. Vazquez, H. J. Thomas, Tetrahedron Lett. 49 (2008) 1441–1444.
[47] X. Shi, X. Hana, W. Ma, J. Weia, J. Li, Q. Zhang, Z. Chen, J. Mol. Catal. A: Chem. 341 (2011) 57–62.