Document Type : Original Research Article

Author

Department of Chemistry,Faculty of Sciences, University of Birjand, P.O. BOX 97175-615, Birjand, Iran

Abstract

In this study, Mn (III) salen complex was synthesized and immobilized onto the graphene oxide, which is modified by 3-chloropropyltrimethoxy silane. Heterogeneous catalyst was characterized by X-ray diffraction, transmission electron microscopy, thermogravimetric analysis, fourier transform infrared spectra, nitrogen adsorption−desorption isotherm and atomic absorption spectroscopy. The catalytic activity of heterogeneous Mn (III) salen complex and comparison with its homogeneous analogue was studied for green oxidation of sulfide derivatives using aqueous 30% H2O2 as an oxidant in water media. The results showed that heterogeneous catalyst was highly efficient in this reaction and corresponding products were obtained in good to excellent yields. The advantages of this catalyst include short reaction times, no side reactions, easy and simple work up, mild reaction conditions and excellent selectivity. The heterogeneous nanocatalyst was reused for several runs without significant loss in activity and selectivity.

Graphical Abstract

Mn (III) salen complex supported on graphene oxide nanosheets as a highly selective and recoverable catalyst for the oxidation of sulfides

Keywords

Main Subjects

[1]  J. Drabowski, P. Kielbasinski, M. Mikolajcyk, Synthesis of Sulfoxides; John Wiley and Sons: New York, 1994.
[2]   Z. Shi, C. Zhang, N. Jiao, Chem. Soc. Rev., 2012, 41, 3381-3430.
[3]  R.A. Sheldon, I.W.C. Arend, A. Dijksman, Catal. Today, 2000, 57, 157-166.
[4]   J. Muzart, Tetrahedron, 2003, 59, 5789-5816.
[5]   V. Mahadevan, R.J.M.K. Gebbink, T.D.P. Stack, Curr. Opin. Chem. Biol., 2000, 4, 228-234.
[6]   R.A. Sheldon, I.W.C.E. Arends, Catal. Met. Compl., 2003, 26, 123-155.
[7]    A. Shaabani, E. Farhangi, A. Rahmati, Appl. Catal. A., 2008, 338, 14-19.
[8]   J. Guan, J. Liu, Transit. Met. Chem., 2014, 39, 233-257.
[9]   M. Rong, J. Wang, Y. Shen, J. Han, Catal. Commun., 2012, 20, 51-60.
[10]   S. Bose, A. Pariyar, A.N. Biswas, P. Das, P. Bandyopadhyay, Catal. Commun., 2011, 12, 446-449.
[11]  R.M. Wang, C.J. Hao, Y.F. He, Y.P. Wang, C.G. Xia, Polym. Adv. Technol., 2002, 13, 6-10.
[12]  L.Z. Flores-Lope´z, M. Parra-Hake, R. Somanathan, P.J. Walsh, Organometallics, 2000, 19, 2153-2160.
[13]   R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel, R.V. Jasra, Tetrahedron-Asymmetr., 2001, 12, 433-437.
[14]   A.G. Dossetter, T.F. Jamison, E.N. Jacobsen, Angew. Chem. Int. Edit., 1999, 38, 2398-2400.
[15]   Z. Li, M. Ferna´ndez, E.N. Jacobsen, Org. Lett., 1999, 1, 1611-1613.
[16]    Z. Li, Z. Zheng, H. Cheng, Tetrahedron-Asymmetr., 2000, 11, 1157–1163.
[17]   T. Katsuki, J. Mol. Catal. A- Chem., 1996, 113, 87–107.
[18]  H. Zhang, Y.M. Wang, L. Zhang, G. Gerritsen, H.C.L. Abbenhuis, R.A. Van Santen, C. Li, J. Catal., 2008, 256, 226–236. 
[19]  R.I. Kureshy, I. Ahmad, N.H. Khan, S.H.R. Abdi, K. Pathak, R.V. Jasra, J. Catal., 2006, 238, 134–141.
[20]  R.I. Kureshy, I. Ahmad, N.H. Khan, S.H.R. Abdi, K. Pathak, R.V. Jasra, Tetrahedron-Asymmetr., 2005, 16, 3562–3569.
[21] H. Zhang, S. Xiang, J. Xiao, C. Li, J. Mol. Catal. A. Chem., 2005, 238, 175–184.
[22]  V. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, A. Mallekpoor- Shalamzari, Appl. Catal. A., 2007, 321, 49-57.
[23]  K. Smith, C.H. Liu, Chem. Commun., 2002, 8, 886-887.
[24]  X.C. Zou, X.K. Fu, Y.D. Li, X.B. Tu, S.D. Fu, Y.F. Luo, X.J. Wu, Adv. Synth. Catal., 2010, 352, 163-170.
[25]  I. Kuzniarska-Biernacka, C. Pereira, A.P. Carvalho, J. Pires, C. Freire, Appl. Clay Sci., 2011, 53, 195-203.
[26]  K. Yu, Z.C. Gu, R.N. Ji, L.L. Lou, S.X. Liu, Tetrahedron, 2009, 65, 305-311.
[27]   S. Sahoo, P. Kumar, F. Lefebvre, S.B. Halligudi, Appl. Catal. A., 2009, 354, 17-25.
[28]  A.F. Trindade, P.M.P. Gois, C.A.M. Afonso, Chem. Rev., 2009, 109, 418-514.
[29]  J.M. Fraile, J.I. García, C.I. Herrerías, J.A. Mayoral, E. Pires, Chem. Soc. Rev., 2009, 38, 695-706.
[30]  N.C. Maity, S.H.R. Abdi, R.I. Kureshy, N.H. Khan, E. Suresh, G.P. Dangi, H.C. Bajaj, J. Catal., 2011, 277, 123-127.
[31]  R. Tan, D. Yin, N. Yu, Y. Jin, H. Zhao, D. Yin, J. Catal., 2008, 255, 287-295.
[32] T. Szabo, E. Tombacz, E. Illes, I. Dekany, Carbon, 2006, 44, 537-545.
[33]  M. Zhou, A. Zhang, Z. Dai, C. Zhang, Y.P. Feng, J. Chem. Phys., 2010, 132, 194704.
[34]  M. Stein, J. Wieland, P. Steurer, F. Tolle, R. Mulhaupt, B. Breit, Adv. Synth. Catal., 2011, 353, 523-527.
[35]  S. Donner, H.W. Li, E.S. Yeung, M.D. Porter, Anal. Chem., 2006, 78, 2816-2822.
[36]   S. Pei, H-M. Cheng, Carbon, 2012, 50, 3210-3228.
[37]  M.A. Nasseri, A. Allahresani, H. Raissi. RSC Adv., 2014, 4, 26087-26093.
[38]   M.H. Ali, D. Kriedelbaugh, T. Wencewicz, Synthesis, 2007, 22, 3507-3511
[39]   B. Karimi, M. Ghoreishi-Nezhad, J.H. Clark, Org. Lett., 2005, 7, 625-628
[40]  A. Ghorbani-Choghamarani, B. Ghasemi, Z. Safari, G. Azadi. Catal. Commun., 2015, 60,70-75
[41]  H. Atashin, R. Malakooti. J. Saudi Chem. Soc., 2013, http://dx.doi.org/10.1016/j.jscs.2013.09.007
[42]  A.R. Judy Azar, E. Safaei, S. Mohebbi, Mater. Res. Bull., 2015, 70, 753–761.
[43] M.  Dabiri, M. Koohshari, F. Shafipour, M. Kasmaei, P. Salari, D. MaGee. J. Iran Chem. Soc., DOI 10.1007/s13738-016-0840-z.