Iranian Journal of Chemistry

Iranian Journal of Chemistry

Nickel(II) unsymmetrical salen complex immobilized into three-dimensional mesoporous silica KIT-6 as an efficient heterogeneous catalyst for selective oxidation of hydrocarbons

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
10.22036/cr.2024.435958.1229
Abstract
In this research, the catalytic activity of the nickel(II) complex containing tetradentate unsymmetrical Schiff base ligand H2salenac = salicylideneiminoethyliminopentane-2-one, immobilized into three-dimensional mesoporous silica KIT-6 (KIT-6-pr-NH2-Ni(salenac)) was studied in the epoxidation of alkenes and oxidation of alkanes using 30% hydrogen peroxide as oxidant. First, the effect of various factors such as the type of solvent, the amount of catalyst and the type of oxidant was investigated and according to the results obtained, acetonitrile and 30% hydrogen peroxide were selected as the best solvent and the best oxidant, respectively. Also, the optimal amount of catalyst for the reaction was determined to be 100 mg (0.016 mmol, based on the nickel present in the catalyst). The obtained results showed that this catalyst has a high ability to catalyze the reaction of epoxidation of alkenes and oxidation of alkanes and produce the product with high yield at room temperature (25 °C). Also, this catalyst is stable in the reaction medium and can be recovered and reused up to 5 times.

Graphical Abstract

Nickel(II) unsymmetrical salen complex immobilized into three-dimensional mesoporous silica KIT-6 as an efficient heterogeneous catalyst for selective oxidation of hydrocarbons
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[1] I. W. C. E. Arends, R. A. Sheldon, in: J. -E. Bäckvall (Ed.) Modern Oxidation Methods, Wiley-VCH, Weinheim, 2004.
[2] K. Kamiya, A. Kuwabara, T. Harada, S. Nakanishi, ChemPhysChem 20, 648 (2019)
[3] Q. Zhang, J. D. Gorden, C. R. Goldsmith, Inorg. Chem. 52, 13546 (2013)
[4] W. Wu, H. Jiang, Acc. Chem. Res. 45, 1736 (2012)
[5] A. Bezaatpour, React. Kinet. Mech. Cat. 112, 453 (2014)
[6] M. Behzad, S. Etminani, Appl. Chem. Today 7, 31 (2012)
[7] H. Kargar, A. Adabi Ardakani, N. Feizi, Appl. Chem. Today 14, 9 (2019)
[8] H. R. Mardani, M. Ziari, Res. Chem. Intermed. 44, 6605 (2018)
[9] M. Moosavifar, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, J. Mol. Catal. A: Chem. 377, 92 (2013)
[10] M. Bagherzadeh, M. Hosseini, A. Mortazavi-Manesh, Inorg. Chem. Commun. 107, 107495 (2019)
[11] H. Fu-She, Chem. Soc. Rev. 42, 5270 (2013)
[12] R. Rajarao, T. H. Kim, B. R. Bhat, J. Coord. Chem. 65, 2671 (2012)
[13] V. Thamilarasan, P. Revathi, A. Praveena, J. Kim, V. Chandramohan, N. Sengottuvelan, Inorg. Chim. Acta. 508, 119626 (2020)
[14] P. B. Bhat, B. R. Bhat, New. J. Chem. 39, 4933 (2015)
[15] P. B. Bhat, F. Inam, B. R. Bhat, ACS Comb. Sci. 16, 397 (2014)
[16] T. Maharana, N. Nath, H. C. Pradhan, S. Mantri, A. Routaray, A. K. Sutar, Reac. Func. Polym. 171, 105142 (2022)
[17] M. Bazarganipour, M. Salavati-Niasari, Chem. Eng. J. 286, 259 (2016)
[18] A. Allahresani, J Iran. Chem Soc. 14, 1051 (2017)
[19] A. Ghorbani-Choghamarani, B. Tahmasbi, F. Arghand, S. Faryadi, RSC Adv. 5, 92174 (2015)
[20] M. Nikoorazm, A. Ghorbani-Choghamarani, H. Mahdavi, S. M. Esmaeili, Microporous Mesoporous Mater. 211, 174 (2015)
[21] T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Appl. Organometal. Chem. 32, e3974 (2018)
[22] J. Montgomery, Angew Chem. Int. Ed. 43, 3890 (2004)
[23] A. Saxena, A. Kumar, S. Mozumdar, J. Mol. Catal. A: Chem. 269, 35 (2007)
[24] F. Kleitz, S. H. Choi, R. Ryoo, Chem. Commun. 17, 2136 (2003)
[25] F. Zhang, Y. Zheng, Y. Cao, C. Chen, Y. Zhan, X. Lin, Q. Zheng, K. Wei, J. Zhu, J. Mater. Chem. 19, 2771 (2009)
[26] R. J. Kalbasi, N. Mosadegh, J. Inorg. Organomet. Polym. 22, 404 (2012)
[27] M. Hatefi Ardakani, M. Aliavazi, J. Porous Mater. 31, 473 (2024).
[28] S. Bhunia, S. Koner, Polyhedron 30, 1857 (2011)
[29] A. Allahresani, J. Iran. Chem. Soc. 14, 1051 (2017)
[30] M. S. S. Adam, Appl. Organometal. Chem. 32, e4234 (2018)
[31] S. Haghshenas Kashani, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, Catal. Lett. 148, 1110 (2018)
[32] W. Fan, D. Shi, B. Feng, Catal. Commun. 74, 1 (2016)
[33] M. Mirzaee, B. Bahramian, P. Gholampour, S. Teymouri, T. Khorsand, Appl. Organometal. Chem. 33, e4792 (2019)
 

  • Receive Date 22 January 2024
  • Revise Date 13 March 2024
  • Accept Date 14 March 2024