Manganese porphyrin supported on activated carbon as a new catalyst for epoxidation of alkenes with hydrogen peroxide

Iranian Journal of Catalysis

مقاله 6، دوره 13، شماره 2، شهریور 2023، صفحه 177-185   

نوع مقاله: Articles

شناسه دیجیتال (DOI): 10.30495/ijc.2023.1973860.1979

نویسندگان

Saeed Rayati^{* 1}؛ Makan Etefagh¹؛ Majid Masteri-Farahani²

¹Department of Chemistry, K.N. Toosi University of Technology, P.O. Box 16315‐1618, Tehran 15418, Iran.

²Faculty of Chemistry, Kharazmi University, P.O. Box 15719-14911, Tehran, Iran.

چکیده

The Manganese complex of meso-tetrakis (4-carboxyphenyl) porphyrin was immobilized onto the surface of functionalized activated carbon and used as a heterogeneous catalyst for the oxidation of different alkenes. The heterogenized catalyst has been fully characterized using Ultraviolet–visible (UV-Vis), Fourier-transform infrared (FTIR), and atomic absorption spectroscopies as well as thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and nitrogen adsorption-desorption (BET method) analyses. The Catalytic activity of the catalyst was investigated in the epoxidation of alkenes with H₂O₂ as a green oxidant. The influence of different parameters including time of reaction, molar ratio of catalyst, imidazole, and amount of oxidant on the efficiency of the catalyst was investigated. Complete conversion of the indene, α-methyl styrene, and 4-methyl styrene was achieved after 4 h at room temperature.

کلیدواژه‌ها

Catalyst؛ Manganese porphyrin؛ Amine functionalized activated carbon؛ Epoxidation

مراجع

[1] F.P. Ballistreri, R.M. Toscano, M.E. Amato, A. Pappalardo, C. Gangemi, S. Spidalieri, R. Puglisi, G. Trusso Sfrazzetto, Catalysts.8 (2018) 129.

[2] S.E. Denmark, D.C. Forbes, D.S. Hays, J.S. DePue, R. Wilde, J. Org. chem. 60 (1995) 1391-1407.

[3] W. Wang, C. Li, Y. Pi, J. Wang, R. Tan, D. Yin, Catal. Sci. Technol. 9 (2019) 5626-5635.

[4] T. Ma, C. Xu, F. Liu, Y. Feng, W. Zhang, W. Tang, H. Zhang, X. Li, Y. Nie, S. Zhao, Y. Li, D. Ji, Z. Fang, W. He, K. Guo, Mol. Catal. 541 (2023) 113074.

[5] G. Grigoropoulou, J.H. Clark, J.A. Elings, Green Chem. 5 (2003) 1-7.

[6] P. Zhou, X. Wang, B. Yang, F. Hollmann, Y. Wang, RSC adv.7 (2017) 12518-12523.

[7] B. Rezazadeh, A.R. Pourali, A. Banaei, H. Behniafar, J. Coord. Chem. 72 (2019) 3401-3416.

[8] X.T. Ma, X.H. Lu, C.C. Wei, Z.S. Zhao, H.J. Zhan, D. Zhou, Q.H. Xia, Catal. Commun. 67 (2015) 98-102.

[9] J. Jiang, J.X. Wang, X.T. Zhou, H.Y. Chen, H.B. Ji, Eur. J. Inorg. Chem. 2018 (2018) 2666-2674.

[10] X.T. Zhou, Q.H. Tang, H.B Ji, Tetrahedron Lett. 50 (2009) 6601-6605.

[11] L. Li, H.J. Song, X.G. Meng, R.Q. Yang, N. Zhang, Tetrahedron Lett. 59 (2018) 2436-2439.

[12] K. Maljutenko, V. Borovkov, D. Kananovich, I. Järving, M. Lopp, Tetrahedron. 74 (2018) 661-664.

[13] S. Rayati, F. Nejabat, F. Panjiali, Catal. Commun. 122 (2019) 52-57.

[14] S. Rayati, F. Nejabat, S. Zakavi, Inorg. Chem. Commun. 40 (2014) 82-86.

[15] S. Rayati, P. Nafarieh, Appl. Organomet. Chem. 33 (2019) e4789.

[16] A. Rezaeifard, M. Jafarpour, S. Rayati, R. Shariati, Dyes Pigm. 80 (2009) 80-85.

[17] S. Zakavi, A.G. Mojarrad, S. Rayati, J. Mol. Catal. A. Chem. 363 (2012) 153-158.

[18] R. Marcos da Silva Junior, E. Henrique dos Santos, S. Nakagaki, Mol. Cat. 541 (2023) 113080.

[19] A.S. Estrada-Montaño, V. Gómez-Benítez, A. Camacho-Dávila, E. Rivera, D. Morales-Morales, G. Zaragoza-Galán, J. Porphyr. Phthalocyanines. 26 (2022) 821-836.

[20] V.S. Da Silva, S. Nakagaki, G.M. Ucoski, Y.M. Idemori, G. DeFreitas-Silva, RSC adv. 5 (2015) 106589-106598.

[21] J.T. Groves, T.E. Nemo, R.S. Myers, J. Am. Chem. Soc. 101 (1979) 1032-1033.

[22] J.T. Groves, Y. Watanabe, Inorg. Chem. 25 (1986) 4808-4810.

[23] D. Mohajer, G. Karimipour, M. Bagherzadeh, New. J. Chem. 28 (2004) 740-747.

[24] Z.L. Magnuson, R.W. Larsen, Inorganica. Chim. Acta. 552 (2023) 121483.

[25] A. Bahuguna, A. Kumar, V. Krishnan, Asian J. Org. Chem. 8 (2019) 1263-1305.

[26] A.R. Silva, C. Freire, B. De Castro, Carbon. 14 (2004) 3027-3030.

[27] M. Sadiq, M. Khan, M. Numan, R. Aman, S. Hussain, M. Sohail Ahmad, S. Sadiq, M. Abid Zia, H. Ur Rashid, R. Ali, Journal. Chem. 2017 (2017) 5732761.

[28] J.S. Choi, T.H. Kim, K.Y. Choo, J.S. Sung, M.B. Saidutta, S.D. Song, Y.W. Rhee, J. Porous Mater. 12 (2005) 301-310.

[29] E.I. El-Shafey, S.N. Ali, S. Al-Busafi, H.A. Al-Lawati, J. Environ, Chem. Eng. 4 (2016) 2713-2724.

[30] S. Rayati, E. Bohloulbandi, C. R. Chim. 17 (2014) 62-68.

[31] S. Rayati, E.K. Chegini, Macroheterocycles. 9 (2016) 151-155.

[32] S. Rayati, F. Nejabat, C. R. Chim. 20 (2017) 967-974.

[33] F. Nejabat, S. Rayati, J. Ind. Eng. Chem. 69 (2019) 324-330.

[34] S. Rayati, N. Pournaser, F. Nejabat, P. Nafarieh, Inorg. Chem. Commun. 107 (2019) 107447.

[35] S. Rayati, Z. J. Sheybanifard, Porphyr. Phthalocyanines. 19 (2015) 622-630.

[36] S. Rayati, S. Malekmohammadi, J. Exp. Nanosci. 11 (2016) 872-883.

[37] A. Mavrogiorgou, M. Papastergiou, Y. Deligiannakis, M. Louloudi, J. Mol. Catal. A. Chem. 393 (2014) 8-17.

[38] A. Simaioforidou, M. Papastergiou, A. Margellou, D. Petrakis, M. Louloudi, J. Mol. Catal. A. Chem. 426 (2017) 516-525.

[39] E. Assady, B. Yadollahi, M. Riahi Farsani, M. Moghadam, Appl. Organomet. Chem. 29 (2015) 561-565.

[40] S.S. Tareq, M.I. Saiman, T.Y.Y. Hin, A.H. Abdullah, U. Rashid, Bull. Chem. React. Eng. Catal. 13 (2018) 373-385.

[41] A.D. Adler, F.R. Longo, W. Shergalis, J. Am. Chem. Soc. 86 (1964) 3145-3149.

[42] J.W. Buchler, G. Eikelmann, L. Puppe, K. Rochbock, H.H. Schneehage, D. Weck, Lieb. Ann. Chem. 745 (1971) 135-151.

[43] M. Masteri-Farahani, M.K. Alavijeh, M.S. Hosseini, React. Kinet. Mech. Catal. 130 (2020) 303-315.

[44] A. Paradisi, E.M. Johnston, M. Tovborg, C.R. Nicoll, L. Ciano, A. Dowle, J. McMaster, Y. Hancock, G. Davies, P.H. Walton, J. Am. Chem. Soc. 141 (2019) 18585-18599.

[45] S. Rayati, D. Moradi, F. Nejabat, New J. Chem. 44 (2020) 19385-19392.