Selective oxidation of alcohols with hydrogen peroxide in the presence of novel and reusable catalyst of nickel-isatin Schiff base complex immobilized into MCM-41

Document Type : Original Article

Authors

1 Department of Chemistry, Faculty of Science, Vali-e -Asr University of Rafsanjan, Rafsanjan, Iran

2 Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran

3 Department of Physics, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran

Abstract

In this research, firstly, MCM-41 mesoporous was synthesized and amino-modified by 3-aminopropyltriethoxysilane (3-APTES), and subsequently by adding of isatin, imine-functionalized MCM-41 was obtained. Then by adding of NiCl2.6H2O salt to the imine-functionalized MCM-41, the Ni-isatin Schiff base complex anchored into MCM-41 was prepared as a novel and heterogeneous catalyst. The synthesized catalyst was characterized by ICP, FT-IR, XRD, SEM, BET and TGA techniques. The prepared catalyst was used for selective oxidation of primary and secondary alcohols with hydrogen peroxide 30%. In this catalytic system, the effect of different parameters such as solvent, temperature, catalyst amount, and kind of oxidant was studied and according to the obtained results, acetonitrile and hydrogen peroxide 30% were selected as the best solvent and oxidant, respectively. Also, the results showed that in this catalytic system, the primary and secondary alcohols were converted to corresponding aldehydes and ketones with high selectivity and yield of 73-90%. Furthermore, the prepared catalyst can be recovered and reused four times without significant loss of its catalytic activity.

Graphical Abstract

Selective oxidation of alcohols with hydrogen peroxide in the presence of novel and reusable catalyst of nickel-isatin Schiff base complex immobilized into MCM-41

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References

1) É. Balogh-Hergovich, G. Speier, J. Mol. Catal. A: Chem. 44 (2005) 79.
2) M.J. Schultz, M.S. Sigman, Tetrahedron 62 (2006) 8227. 
3) M. Arshadi, M. Ghiaci, Appl. Catal. A: Gen. 399 (2011) 75.
4) A. Bezaatpour, F. Shekh-Hasani, J. Appl. Chem. 10 (2016) 11.
5) L. Canali, D.C. Sherington, Chem. Soc. Rev. 28 (1999) 85.
6) C.D. Nunes, M. Pillinger, A. Valente, A.D. Lopez, I.S. Goncalves, Inorg. Chem. Commun. 6 (2003) 1228.
7) M. Salavati-Niasari, E. Zamani, M. Bazarganipour, Appl. Clay Sci. 38 (2007) 9.
8) M. Heitbaum, F. Glorius, I. Escher, Angew. Chem. Int. Ed. 45 (2006) 4732. 
9) C. Li, H.D. Zhang, D.M. Jiang, Q.H. Yang, Chem. Commun. 6 (2007) 547. 
10) M. Nikoorazm, A. Ghorbani-Choghamarani, F. Ghorbani, H. Mahdavi, Z. Karamshahi, J. Porous Mater. 22 (2015) 261.
11) M. Hajjami, S. Rahmani, J. Porous Mater. 22 (2015) 1265. 
12) M.A. Ali, A.H. Mirza, H.J.H.A. Bakar, P.V. Bernhardt, Polyhedron 30 (2011) 556. 
13) S.H. Sumrra, A.H. Atif, M.N. Zafar, M. Khalid, M.N. Tahir, M.F. Nazar, M.A. Nadem, A.A.C. Braga, J. Mol. Struct. 1166 (2018) 110. 
14) A.G.B. Dileepan, T.D. Prakash, A.G. Kumar, P.S. Rajam, V.V. Dhayabaran, R. Rajaram, J. Photochem. Photobiol. B 183 (2018) 191. 
15) G. Mather, P.K. Sharma, S. Nain, Curr. Bioact. Compd. 14 (2018) 211. 
16) M.A. Ali, H.J.H.A. Bakar, A.H. Mirza, S.J. Smith, L.R. Gahan, P.V. Bernhardt, Polyhedron 27 (2008) 71.
17) M.C. Rodriguez-Arguelles, S. Mosquera-Vazquez, P. Touron-Touceda, J. Sanmartin-Matalobos, A.M. Garcia-Deibi, M. Belicchi-Ferrari, G. Pelosi, C. Pelizzi, F. Zani, J. Inorg. Biochem. 101 (2007) 138. 
18) M. Hajjami, Z. Yousofvand, Catal. Lett. 145 (2015) 1733. 19) S. Sobhani, F. Zarifi, Chin. J. Catal. 36 (2015) 555. 
20) R. Antony, T.D. Manickam, P. Kollu, P.V. Chandrasekar, K. Karuppasamy, S. Balakumar, RSC Adv. 4 (2014) 24820. 
21) S. Sobhani, S. Asadi, M. Salami, F. Zarifi, J. Organomet. Chem. 822 (2016) 154. 
22) D. Chatterjee, A. Mitra, J. Mol. Catal. A: Chem. 144 (1999) 363. 
23) S. Bhunia, S. Koner, Polyhedron 30 (2011) 1857. 
24) D. Ramakrishna, B.R. Bhat, R. Karvembu, Chem. Commun. 11 (2010) 498. 
25) A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasebi, RSC Adv. 6 (2016) 56458. 
26) T. Tamoradi, M. Ghadermarzi, A. Ghorbani- Choghamarani, Appl. Organometal. Chem. (2017). 
27) S. Nazarzadeh, A. Ghorbani-Choghamarani, E. Tahanpesar, J. Iran. Chem Soc. (2017).
28) J.D. Koola, J.K. Kochi, Inorg. Chem. 26 (1987) 908.29) Q. Cai
, W.-Y. Lin, F.-S. Xiao, W.-Q. Pang, X.-H. Chen, B.-S. Zou, Microporous Mesoporous Mater. 32 (1999) 1. 
30) V. Mahdavi, M. Mardani, Res. Chem. Intermed. 41 (2015) 8907. 
31) H. Mahdavi, M. Nikoorazm, A. Ghorbani- Choghamarani, S. Arshadi, J. Porous Mater. 23 (2016) 75. 
32) X. Wang, G. Wu, W. Wei, Y. Sun, Transition Met. Chem. 35 (2010) 213. 
33) M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, Res. Chem. Intermed. 42 (2016) 4621. 
34) P. Karandikar, K.C. Dhanya, S. Deshpande, A.J. Chandwadkar, S. Sivasanker, M. Agashe, Catal. Commun. 5 (2004) 69. 
35) M. Nikoorazm, A. Ghorbani-Choghamarani, A. Jabbari, J. Porous Mater. 23 (2016) 967.
36) T. Joseph, M. Hartmannb, S. Ernst, S.B. Halligudi, J. Mol. Catal. A: Chem. 207 (2004) 131. 
37) Y. Gang, C. Xing, W. Xiaoli, X. Weihong, X. Nanping, Chin. J. Catal. 34 (2013) 1326. 
38) M. Hatefi Ardakani, S. Saeednia, P. Iranmanesh, B. Konani, J. Inorg. Organomet. Polym. 27 (2017) 146.
39) X. Sun, Y. Zheng, L. Sun, Q. Lin, H. Su, C. Qi, Nano-Struct. Nano-Objects 5 (2016) 7. 
40) S.H. Kashani, M.Moghadam. S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, Catal. Lett. (2018). 
41) M.R. Farsani, B. Yadollahi, J. Mol. Catal. A: Chem. 392 (2014) 8. 
42) S.M. Islam, M. Mobarak, P. Mondal, A.S. Roy, N. Salam, D. Hossein, S. Mondal, Transition Met. Chem. 37 (2012) 97. 
43) M.J. Schultz, M.S. Sigman, Tetrahedron 62 (2006) 109 8227. 
44) M. Ghorbanlo, A.M. Alamoti, J. Porous Mater. (2016). 
45) P. Wang, Z. Dong, Y. Lei, Y. Du, H. Li, H. Yang, Y. Nie, J. Ma, J. Porous Mater. 20 (2013) 277.  
46) X.Y. Cheng, K.F. Li, Q.J. Wang, C.Y. Wang, T. K. Ying, Chin. Chem. Lett. 23 (2012) 801. 
47) A.R. Pourali, M. Tabaean, S.M.R. Chem. Lett. 23 (2012) 21. 
48) G.R. Najafi, Chin. Chem. Lett. 21 (2010) 1162. 
49) F. Rajabi, B. Karimi, J. Mol. Catal. A: Chem. 232 (2005) 95.
Iranian Journal of Chemistry
Volume 1, Issue 1 - Serial Number 1
January 2019
Pages 95-109

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History

  • Receive Date: 05 August 2018
  • Revise Date: 16 October 2018
  • Accept Date: 26 November 2018

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