Synthesis of chitosan-based heterogeneous catalyst and its performance in nitroarenes reduction reactions

Subject Areas : Synthesis and Characterization of Nanostructures

Parisa Esmaeilzadeh ¹ , Maryam Mohammadikish ²

1 - Inorganic Chemistry Department, Faculty of Chemistry, Kharazmi University, Tehran, Iran
2 - Inorganic Chemistry Department, Faculty of Chemistry, Kharazmi University, Tehran, Iran

Received: 2024-08-30 Accepted : 2024-09-21 Published : 2024-08-26

Keywords: Schiff base, Nitroarene reduction, Chitosan, Nickel.,

Abstract :

Design and synthesis of heterogeneous catalysts to reduce nitroarenes are an important and essential technique in green chemistry. In this research, C/B/Ni heterogeneous catalyst was prepared through functionalization of the chitosan and immobilization of nickel cations on the surface of the chitosan. The ammine groups of the chitosan reacted with aldehyde groups of 2-(4-chlorophenyl thio) benzaldehyde via Schiff base condensation and NS donor groups which can bind to metal, placed on the surface of the chitosan. In the end, NS donor groups coordinated to Ni²⁺ cations. After characterization of the prepared catalyst with various physicochemical technique, its performance was considered in reduction of nitroarenes to aminoarenes. The prepared catalyst depicted a very good efficiency in reduction of nitroarenes in aqueous media, room temperature, and relatively short time. Moreover, recovered catalyst was utilized in catalytic cycles and its efficiency is reportable after three consecutive cycles without negligible reduce. 

References:

[1] S. Panigrahi, S. Basu, S. Praharaj, S. Pande, S. Jana, A. Pal, S.K. Ghosh, T. Pal, The Journal of Physical Chemistry C, 111, 4596 (2007) 4596.
[2] A.K. Patra, N.T. Vo, D. Kim, Applied Catalysis A: General, 538, 148 (2017).
[3] R. Begum, R. Rehan, Z.H. Farooqi, Z. Butt, S. Ashraf, Journal of Nanoparticle Research, 18, 231 (2016).
[4] A. Ayati, B. Tanhaei, F.F. Bamoharram, A. Ahmadpour, P. Maydannik, M. Sillanpää, Separation and Purification Technology, 171, 62 (2016).
[5] M.A. Oturan, J. Peiroten, P. Chartrin, A.J. Acher, Environmental Science & Technology, 34, 3474 (2000).
[6] X. Zhao, A. Li, X. Quan, S. Chen, H. Yu, S. Zhang, Chemosphere, 238, 124636 (2020).
[7] S. Aghajani, M. Mohammadikish, Dalton Transactions, 10644 (2024).
[8] S. Aghajani, M. Mohammadikish, M. Khalaji-Verjani, Langmuir, 39, 8484 (2023).
[9] B. Gholami, M. Mohammadikish, M. Niakan, ACS Applied Nano Materials, 6, 2864 (2023).
[10] K.I. Min, J.S. Choi, Y.M. Chung, W.S. Ahn, R. Ryoo, P. Lim, Applied Catalysis A: General, 337, 97 (2008).
[11] F. L'eplattenier, P. Matthys, F. Calderazzo, Inorganic Chemistry, 9, 342 (1970).
[12] N. Zhang, Y. Qiu, H. Sun, J. Hao, J. Chen, J. Xi, J. Liu, B. He, Z.-W. Bai, ACS Applied Nano Materials, 4, 5854 (2021).
[13] A. Lucchesi Schio, M.R. Farias Soares, G. Machado, T. Barcellos, ACS Sustainable Chemistry & Engineering, 9, 9661 (2021).
[14] S. Liu, J.I. Amaro-Estrada, M. Baltrun, I. Douair, R. Schoch, L. Maron, S. Hohloch, Organometallics, 40, 107 (2021).
[15] S. Aghajani, M. Mohammadikish, Langmuir, 38, 8686 (2022).
[16] J. T. Du, M. Qiao, Y. Pu, J.X. Wang, J.F. Chen, Applied Catalysis A: General, 624, 118323 (2021).
[17] H.G. Bilgicli, H. Burhan, F. Diler, K. Cellat, E. Kuyuldar, M. Zengin, F. Sen, Microporous and Mesoporous Materials, 296, 110014 (2020).
[18] E.N. Nishida, E.C. Leopoldino, L. Zaramello, H.A. Centurion, R.V. Gonçalves, R.F. Affeldt, C.E. Campos, B.S. Souza, ChemCatChem, 14, e202101596 (2022) e202101596.
[19] M. Gao, J. Wang, W. Shang, Y. Chai, W. Dai, G. Wu, N. Guan, L. Li, Catalysis Today, 410, 237 (2023).
[20] V. Goyal, N. Sarki, B. Singh, A. Ray, M. Poddar, A. Bordoloi, A. Narani, K. Natte, ACS Applied Nano Materials, 3, 11070 (2020).
[21] M. Mohammadikish, S.H. Hashemi, Journal of Materials Science, 54, 6164 (2019).
[22] R. Antony, T. Arun, S.T.D. Manickam, International journal of biological macromolecules, 129, 615 (2019).
[23] V. Zargar, M. Asghari, A. Dashti, ChemBioEng reviews, 2, 204 (2015).
[24] H. Schiff, Justus Liebigs Annalen der Chemie, 131, 118 (1864).
[25] M. Dash, F. Chiellini, R.M. Ottenbrite, E. Chiellini, Progress in polymer science, 36, 981 (2011).