Citation: Maryam Hajjami, Farshid Ghorbani, Sedighe Rahimipanah, Safoora Roshani. Efficient preparation of Zr(IV)-salen grafted mesoporous MCM-41 catalyst for chemoselective oxidation of sulfides to sulfoxides and Knoevenagel condensation reactions[J]. Chinese Journal of Catalysis, ;2015, 36(11): 1852-1860. doi: 10.1016/S1872-2067(15)60968-8 shu

Efficient preparation of Zr(IV)-salen grafted mesoporous MCM-41 catalyst for chemoselective oxidation of sulfides to sulfoxides and Knoevenagel condensation reactions

1.
a Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran;

Corresponding author: Maryam Hajjami,
Received Date: 19 June 2015
Available Online: 6 September 2015

Zr(IV)-salen-MCM-41 was prepared by reaction of NH₂-MCM-41 with salicylaldehyde to afford Schiff base ligands. Thereafter, ZrOCl₂·8H₂O was reacted with the Schiff base ligands for complex formation. The structural properties of the synthesized materials were investigated by a number of analytical techniques including X-ray diffraction, N₂ sorption-desorption, thermogravimetric analysis, Fourier transform infrared spectroscopy, inductively coupled plasma atomic emission spectroscpopy, and energy dispersive X-ray spectroscopy. Catalytic studies of the mesoporous materials functionalized with Zr(IV)-Schiff base complexes were investigated and extended to selective oxidation of sulfides to sulfoxides and the Knoevenagel condensation reactions of aldehydes with malononitriles and ethyl cyanoacetate. Additionally, catalyst recycling of the Zr-salen-MCM-41 materials was also studied.
- Zr(IV)-salen-MCM-41,
- Mesoporous material,
- Sulfoxide,
- Knoveonagel condensation,
- Sulfide
1. [1]
  [1] Vartuli J C, Shih S S, Kresge C T, Beck J S. Stud Surf Sci Catal, 1998, 117: 13
2. [2]
  [2] Knöfel C, Martin C, Hornebecq V, Llewellyn P L. J Phys Chem C, 2009, 113: 21726
3. [3]
  [3] Meléndez-Ortiz H I, Perera-Mercado Y, Mercado-Silva J A, Olivares-Maldonado Y, Griselda G, García-Cerda L A. Ceram Int, 2014, 40: 9701
4. [4]
  [4] Eimer G A, Costa M B G, Pierella L B, Anunziata O A. J Colloid Interface Sci, 2003, 263: 400
5. [5]
  [5] Dey R K, Oliveira F J V E, Oliveira C. Colloids Surf A, 2008, 324: 41
6. [6]
  [6] Taguchi A, Schuth F. Microporous Mesoporous Mater, 2005, 77: 1
7. [7]
  [7] Jiang T S, Cheng J L, Liu W P, Fu L, Zhou X P, Zhao Q, Yin H B. J Solid State Chem, 2014, 218: 71
8. [8]
  [8] Hajjami M, Ghorbani F, Bakhti F. Appl Catal A, 2014, 470: 303
9. [9]
  [9] Wang G, Otuonye A N, Blair E A, Denton K, Tao Z, Asefa T. J Solid State Chem, 2009, 182: 1649
10. [10]
  [10] Rigby S P, Fairhead M, van der Walle C F. Curr Pharm Des, 2008, 14: 1821
11. [11]
  [11] Mehraban Z, Farzaneh F. Microporous Mesoporous Mater, 2006, 88: 84
12. [12]
  [12] Selvam P, Bhatia S K, Sonwane C G. Ind Eng Chem Res, 2001, 40: 3237
13. [13]
  [13] Hoffmann F, Cornelius M, Morell J, Froba M. Angew Chem Int Ed, 2006, 45: 3216
14. [14]
  [14] Carreno M C. Chem Rev, 1995, 95: 1717
15. [15]
  [15] Fernandez I, Khiar N. Chem Rev, 2003, 103: 3651
16. [16]
  [16] Egami H, Katsuki T. J Am Chem Soc, 2007, 129: 8940
17. [17]
  [17] Li G, Qian H F, Jin R C. Nanoscale, 2012, 4: 6714
18. [18]
  [18] Kon Y, Yokoi T, Yoshioka M, Tanaka S, Uesaka Y, Mochizuki T, Sato K, Tatsumi T. Tetrahedron, 2014, 70: 7584
19. [19]
  [19] Gogoi P, Kalita M, Bhattacharjee T, Barman P. Tetrahedron Lett, 2014, 55: 1028
20. [20]
  [20] Sharma V B, Jain S L, Sain B. J Mol Catal A, 2004, 212: 55
21. [21]
  [21] Mohammadinezhad A, Nasseri M A, Salimi M. RSC Adv, 2014, 4: 39870
22. [22]
  [22] Bahrami K. Tetrahedron Lett, 2006, 47: 2009
23. [23]
  [23] Bagherzadeh M, Tahsinia L, Latifi R, Ellern A, Woo L K. Inorg Chim Acta, 2008, 361: 2019
24. [24]
  [24] Wu X F. Tetrahedron Lett, 2012, 53: 4328
25. [25]
  [25] Zeng Q L, Gao Y X, Dong J Y, Weng W, Zhao Y F. Tetrahedron Asymmetry, 2011, 22: 717
26. [26]
  [26] Tanaka H, Nishikawa H, Uchida T, Katsuki T. J Am Chem Soc, 2010, 132: 12034
27. [27]
  [27] Kiriharaa M, Yamamoto J, Noguchi T, Hirai Y. Tetrahedron Lett, 2009, 50: 1180
28. [28]
  [28] Karimi B, Ghoreishi-Nezhad M, Clark J H. Org Lett, 2005, 7: 625
29. [29]
  [29] Knoevenagel E. Ber Deutschen Chem Ges, 1894, 27: 2345
30. [30]
  [30] Nawrot-Modranka J, Nawrot E, Graczyk J. Eur J Med Chem, 2006, 41: 1301
31. [31]
  [31] Zicmanis A, Anteina L. Tetrahedron Lett, 2014, 55: 2027
32. [32]
  [32] Mallouk S, Bougrin K, Laghzizil A, Benhida R. Molecules, 2010, 15: 813
33. [33]
  [33] Liu S, Ni Y X, Yang J G, Hu H N, Ying A G, Xu S L. Chin J Chem, 2014, 32: 343
34. [34]
  [34] Girija D, Bhojya Naik H S, Kumar B V, Sudhamani C N, Harish K N. Lett Org Chem, 2013, 10: 468
35. [35]
  [35] Mase N, Horibe T. Org Lett, 2013, 15: 1854
36. [36]
  [36] Rao P S, Venkataratnam R V. Tetrahedron Lett, 1991, 32: 5821
37. [37]
  [37] Reddy T I, Varma R S. Tetrahedron Lett, 1997, 38: 1721
38. [38]
  [38] Bigi F, Chesini L, Maggi R, Sartori G. J Org Chem, 1999, 64: 1033
39. [39]
  [39] Kumbhare R M, Sridhar M. Catal Commun, 2008, 9: 403
40. [40]
  [40] Malakooti R, Bardajee G R, Mahmoudi H, Kakavand N. Catal Lett, 2013, 143: 853
41. [41]
  [41] Malakooti R, Bardajee G R, Hadizadeh S, Atashin H, Khanjari H. Transition Met Chem, 2014, 39: 47
42. [42]
  [42] Ma L, Su F, Zhang X H, Song D Y, Guo Y H, Hu J L. Microporous Mesoporous Mater, 2014, 184: 37
43. [43]
  [43] Das S, Bhunia S, Maity T, Koner S. J Mol Catal A, 2014, 394: 188
44. [44]
  [44] Dhara K, Sarkar K, Srimani D, Saha S K, Chattopadhyay P, Bhaumik A. Dalton Trans, 2010, 39: 6395
45. [45]
  [45] Nikoorazm M, Ghorbani-Choghamarani A, Mahdavi H, Esmaeili S M. Microporous Mesoporous Mater, 2015, 211: 174
46. [46]
  [46] Bordoloi A, Amrute A P, Halligudi S B. Catal Commun, 2008, 10: 45
47. [47]
  [47] Luo Y, Lin J. Microporous Mesoporous Mater, 2005, 86: 23
48. [48]
  [48] Wang X L, Wu G D, Wei W, Sun Y H. Catal Lett, 2010, 136: 96
49. [49]
  [49] Chen H X, Wang Y C. Ceram Int, 2002, 28: 541
50. [50]
  [50] Kumar D, Schumacher K, du Fresne von Hohenesche C, Grun M, Unger K K. Colloids Surfaces A, 2001, 187-188: 109
51. [51]
  [51] Meléndez-Ortiz H I, Perera-Mercado Y A, García-Cerda L A, Mercado-Silva J A, Castruita G. Ceram Int, 2014, 40: 4155
52. [52]
  [52] McKittrick M W, Jones C W. Chem Mater, 2003, 15: 1132
53. [53]
  [53] Ghorbani F, Habibollah Y, Mehraban Z, Celik M S, Ghoreyshi A A, Anbia M. J Taiwan Inst Chem Eng, 2013, 44: 821
54. [54]
  [54] Zhao D Y, Huo Q S, Feng J L, Chmelka B F, Stucky G D. J Am Chem Soc, 1998, 120: 6024
55. [55]
  [55] Carraro P, Elías V, García Blanco A A, Sapag K, Eimer G, Oliva M. Int J Hydrogen Energy, 2014, 39: 8749
56. [56]
  [56] Bhagiyalakshmi M, Yun L J, Anuradha R, Jang H T. J Hazard Mater, 2010, 175: 928
57. [57]
  [57] Kim S, Ida J, Guliants V V, Lin Y S. J Phys Chem B, 2005, 109: 6287
58. [58]
  [58] Shahbazi A, Younesi H, Badiei A. Chem Eng J, 2011, 168: 505
59. [59]
  [59] Li J S, Miao X Y, Hao Y X, Zhao J Y, Sun X Y, Wang L J. J Colloid Interface Sci, 2008, 318: 309
60. [60]
  [60] Parida K M, Rath D. J Mol Catal A, 2009, 310: 93
61. [61]
  [61] Heidari A, Younesi H, Mehraban Z. Chem Eng J, 2009, 153: 70
62. [62]
  [62] Das R, Chakraborty D. Tetrahedron Lett, 2010, 51: 6255
63. [63]
  [63] Rostami A, Atashkar B, Gholami H. Catal Commun, 2013, 37: 69
64. [64]
  [64] Yue C B, Mao A Q, Wei Y Y, Lu M J. Catal Commun, 2008, 9: 1571
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沈阳化工大学材料科学与工程学院沈阳 110142