Iron (III)-schiff base immobilized on porous silica and magnetite: a comparison study for oxidation of benzylic alcohols and sulfides

Document Type : Original Article

Authors

Department of Chemistry, Faculty of Basic Sciences, University of Birjand, Birjand, Iran

Abstract

The iron (III) Schiff base complex was immobilized on magnetic silica as well as mesoporous silica substrates and characterized by XRD, TEM, FT-IR, AAS, VSM techniques, and in the case of mesoporous silica, it was also identified with N2 adsorption/desorption and TGA methods. These materials were applied for oxidation of benzyl alcohols and sulfides with hydrogen peroxide as a green oxidant. The effect of catalyst structures was studied in the mentioned reactions. The results showed that using of mesoporous silica in the oxidation of sulfides and benzyl alcohols with hydrogen peroxide in the optimal reaction conditions provided a higher catalytic yield in the same or even less reaction time, The higher catalytic performance of the mesoporous substrate based on the identifications (carried out by N2 adsorption/desorption technique) can be attributed to the higher surface area of this substrate and the stronger connection of the Schiff base complex of iron (III) to the mesoporous silica (according to leaching test).

Keywords

Main Subjects

This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

References

[1] Mallat, T., & Baiker, A. (2004). Oxidation of alcohols with molecular oxygen on solid catalysts. Chemical reviews, 104(6), 3037-3058.
[2] Najafishirtari, S., Friedel Ortega, K., Douthwaite, M., Pattisson, S., Hutchings, G. J., Bondue, C. J., ... & Behrens, M. (2021). A perspective on heterogeneous catalysts for the selective oxidation of alcohols. Chemistry–A European Journal, 27(68), 16809-16833.
[3] Targhan, H., Evans, P., & Bahrami, K. (2021). A review of the role of hydrogen peroxide in organic transformations. Journal of Industrial and Engineering Chemistry, 104, 295-332.
[4] Kupwade, R. V. (2019). A concise review on synthesis of sulfoxides and sulfones with special reference to oxidation of sulfides. J. Chem. Rev, 1, 99-113.
[5] Tong, Q. L., Fan, Z. F., Yang, J. W., Li, Q., Chen, Y. X., Cheng, M. S., & Liu, Y. (2019). The selective oxidation of sulfides to sulfoxides or sulfones with hydrogen peroxide catalyzed by a dendritic phosphomolybdate hybrid. Catalysts, 9(10), 791.
[6] M Heravi, M., Ghalavand, N., & Hashemi, E. (2020). Hydrogen peroxide as a green oxidant for the selective catalytic oxidation of benzylic and heterocyclic alcohols in different media: an overview. Chemistry, 2(1), 101-178.
[7] Noyori, R., Aoki, M., & Sato, K. (2003). Green oxidation with aqueous hydrogen peroxide. Chemical Communications, (16), 1977-1986.
[8] Védrine, J. C. (2019). Metal oxides in heterogeneous oxidation catalysis: State of the art and challenges for a more sustainable world. ChemSusChem, 12(3), 577-588.
[9] Valange, S., & Védrine, J. C. (2018). General and prospective views on oxidation reactions in heterogeneous catalysis. Catalysts, 8(10), 483.
[10] Huang, A., He, Y., Zhou, Y., Zhou, Y., Yang, Y., Zhang, J., ... & Yang, J. (2019). A review of recent applications of porous metals and metal oxide in energy storage, sensing and catalysis. Journal of Materials Science, 54, 949-973.
[11] Bezaatpour, A., Bozari, N., & Khatami, S. (2019). Green oxidation of sulfides by dioxide molybdenum (VI) schiff base anchored on Fe3O4 nanoparticles in solvent-free condition. Applied Chemistry, 14(50), 55-70.
[12] Peterson, B. M., Herried, M. E., Neve, R. L., & McGaff, R. W. (2014). Oxidation of primary and secondary benzylic alcohols with hydrogen peroxide and tert-butyl hydroperoxide catalyzed by a “helmet” phthalocyaninato iron complex in the absence of added organic solvent. Dalton Transactions, 43(48), 17899-17903.
[13] Neve, R. L., Eidenschink, M. C., Guzei, I. A., Peterson, B. M., Vang, G. M., & McGaff, R. W. (2016). Homogeneous catalytic oxidation of unactivated primary and secondary alcohols employing a versatile “Helmet” phthalocyaninato iron complex catalyst without added organic solvent. ChemistrySelect, 1(16), 5182-5186.
[14] Tan, P., Kwong, H. K., & Lau, T. C. (2015). Catalytic oxidation of water and alcohols by a robust iron (III) complex bearing a cross-bridged cyclam ligand. Chemical Communications, 51(61), 12189-12192.
[15] Rana, J., Sahoo, S. T., & Daw, P. (2021). Homogeneous first-row transition metal catalyst for sustainable hydrogen production and organic transformation from methanol, formic acid, and bio-alcohols. Tetrahedron, 99, 132473.
[16] Geng, L., Zhang, X., Zhang, W., Jia, M., & Liu, G. (2014). Highly dispersed iron oxides on mesoporous carbon for selective oxidation of benzyl alcohol with molecular oxygen. Chemical Communications, 50(22), 2965-2967.
[17] Sahu, D., Silva, A. R., & Das, P. (2015). A novel iron (III)-based heterogeneous catalyst for aqueous oxidation of alcohols using molecular oxygen. RSC advances, 5(96), 78553-78560.
[18] Parmeggiani, C., Matassini, C., & Cardona, F. (2017). A step forward towards sustainable aerobic alcohol oxidation: new and revised catalysts based on transition metals on solid supports. Green Chemistry, 19(9), 2030-2050.
[19] Cheng, W., Jiang, Y., Li, X., Li, Y., Xu, X., Lin, K., & Wang, Y. (2016). Fabrication and application of magnetic nanoreactor with multiple ultrasmall cores and mesoporous shell in Fenton-like oxidation. Microporous and Mesoporous Materials, 219, 10-18.
[20] Geng, L., Zheng, B., Wang, X., Zhang, W., Wu, S., Jia, M., ... & Liu, G. (2016). Fe3O4 nanoparticles anchored on carbon serve the dual role of catalyst and magnetically recoverable entity in the aerobic oxidation of alcohols. ChemCatChem, 8(4), 805-811.
[21] Pal, N., & Bhaumik, A. (2015). Mesoporous materials: versatile supports in heterogeneous catalysis for liquid phase catalytic transformations. RSC Adv, 5, 24363–24391.
[22] Najafishirtari, S., Friedel Ortega, K., Douthwaite, M., Pattisson, S., Hutchings, G. J., Bondue, C. J., ... & Behrens, M. (2021). A perspective on heterogeneous catalysts for the selective oxidation of alcohols. Chemistry–A European Journal, 27(68), 16809-16833.
[23] Balali, M., Keypour, H., Bagherzadeh, M., & Alsadat Mousavi, N. (2019). Synthesis of schiff-base molybdenum complex supported on magnetic nanoparticles Fe3O4@ SiO2 and their application as recyclable catalyst in oxidation of sulfides to sulfoxides. Applied Chemistry, 14(50), 181-192.
[24] Kargar, H., & Keshanizadeh, N. (2018). Biomimetic oxidation of sulfides with sodium periodate catalyzed by multi-wall carbon nanotubes supported Mn porphyrin. Applied Chemistry, 13(46), 281-294.
[25] Lin, Y. S., & Haynes, C. L. (2009). Synthesis and characterization of biocompatible and size-tunable multifunctional porous silica nanoparticles. Chemistry of Materials, 21(17), 3979-3986.
[26] Deng, Y., Cai, Y., Sun, Z., Liu, J., Liu, C., Wei, J., ... & Zhao, D. (2010). Multifunctional mesoporous composite microspheres with well-designed nanostructure: a highly integrated catalyst system. Journal of the American Chemical Society, 132(24), 8466-8473.
[27] Jin, X., Zhang, K., Sun, J., Wang, J., Dong, Z., & Li, R. (2012). Magnetite nanoparticles immobilized Salen Pd (II) as a green catalyst for Suzuki reaction. Catalysis Communications, 26, 199-203.
[28] Wang, Y. M., Wu, Z. Y., Shi, L. Y., & Zhu, J. H. (2005). Rapid functionalization of mesoporous materials: directly dispersing metal oxides into as‐prepared SBA‐15 occluded with template. Advanced Materials, 17(3), 323-327.
[29] Bardajee, G. R., Malakooti, R., Jami, F., Parsaei, Z., & Atashin, H. (2012). Covalent anchoring of copper-Schiff base complex into SBA-15 as a heterogeneous catalyst for the synthesis of pyridopyrazine and quinoxaline derivatives. Catalysis Communications, 27, 49-53.
[30] Bardajee, G. R., Malakooti, R., Abtin, I., & Atashin, H. (2013). Palladium Schiff-base complex loaded SBA-15 as a novel nanocatalyst for the synthesis of 2, 3-disubstituted quinoxalines and pyridopyrazine derivatives. Microporous and Mesoporous Materials, 169, 67-74.
[31] Oliveira, P., Machado, A., Ramos, A. M., Fonseca, I. M., Braz Fernandes, F. M., Botelho do Rego, A. M., & Vital, J. (2007). A new and easy method for anchoring manganese salen on MCM-41. Catalysis letters, 114, 192-197.
Applied Chemistry Today
Volume 19, Issue 70
May 2024
Pages 59-74

Files

Share

How to cite

Statistics