Co (II) complex immobilized on functionalized graphene oxide: An efficient catalyst for epoxidation of alkenes

Document Type : Original Article


Department of Chemistry, Yasuj University, Yasuj, Iran


In this research, the 1, 2-bis‌(4-pyridylthio)ethane (PTE) functionalized grapheme oxide is used as powerful support for immobilization of cobalt complex to deliver a novel heterogeneous catalyst (Co-PTE-GO) for epoxidation of alkenes. The Co-PTE-GO catalyst was characterized by different techniques such as Fourier transform infrared (FT-IR) spectroscopy, thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), energy-dispersive X-ray (EDX), Raman spectroscopy and inductively coupled plasma optical emission spectrometry (ICP-OES). These analyses confirmed high chemical and thermal stability of the designed catalyst. The Co-PTE-GO was used for epoxidation of linear and cyclic alkenes giving corresponding epoxides in high yields (81-97%). This catalyst was recovered and reused at least 4 times with keeping its performance under reaction conditions.


[1] Q. Zhao, C. Bai, W. Zhang, Y. Li, G. Zhang, F. Zhang and X. Fan, Ind. Eng. Chem. Res. 53 (2014) 4232.
[2] W. Xiaoli, W. Gongde, W. Fang, W. Wei and S. Yuhan, Chin. J. Catal. 32 (2011) 1812.
[3] S. A. Hauser, M. Cokoja and F. E. Kühn, Catal. Sci. Technol. 3 (2013) 552.
[4] S. Shaw and J. D. White, Chem. Rev. 119 (2019) 9381.
[5] S. Bellemin-Laponnaz and S. Dagorne, Chem. Rev. 114 (2014) 8747.
[6] X. Jiang, F. Gou, F. Chen and H. Jing, Green Chem. 18 (2016) 3567.
[7] X. Sun, K. Zu, H. Liang, L. Sun, L. Zhang, C. Wang and V. K. Sharma, J. Hazard. Mater. 344 (2018) 1155.
[8] Q. Tang, Y. Wang, J. Zhang, R. Qiao, X. Xie, Y. Wang and Y. Yang, Appl. Organomet. Chem. 30 (2016) 435.
[9] D. H. Nguyen, Y. Morin, L. Zhang, X. Trivelli, F. Capet, S. Paul and R. M. Gauvin, ChemCatChem, 14 (2017) 2652.
[10] S. Koya, Y. Nishioka, H. Mizoguchi and T. Uchida, Angew. Chem. Int. Ed. 51( 2012 ) 8243.
[11] M. H. Valkenberg, and W. F. Holderich, Catal. Rev. 44 (2002) 321.
[12] C. M. Marrodan, D. Berti, F. Liguori and P. Barbaro, Catal. Sci. Technol. 2 (2012) 2279.
[13] H. Kargar, A. Adabi Ardakani and N. Feizi, J. Of Applied Chemistry, 51 (1398) 9, in Persian.
[14] E. Einafshar. A .Haghighiasl, M. Ramezani, A. Hashem Nia and A. Malekzadeh, J. Of Applied Chemistry, 51 (1398) 35, in Persian. 
[15] M. Mirzaee, M. Faghani and A. Keivanloo, J. Of Applied Chemistry, 52 (1398) 135, in Persian.
[16] Z.  Lasemi and B. Sadeghi, J. Of Applied Chemistry, 55 (1399) 149, in Persian.
[17 A.  Maleki, F. Hassanzadeh-Afruzi and S. Bahrami, J. Of Applied Chemistry, 47 (1397) 173, in Persian.
[18] F. Giacalone, V. Campisciano, C. Calabrese, V. La Parola, Z. Syrgiannis, M. Prato and M. Gruttadauria, ACS Nano, 10 (2016) 4627.
[19] Y. Kuwahara, H. Kango and H. Yamashita, Catalysts, 9 (2019) 1993.
[20] A. W. Petrov, D. Ferri, O. Kröcher and J. A.van Bokhoven, Catalysts, 9 )2019 (2303.
[21] F. Chen, C. Kreyenschulte, J. Radnik, H. Lund, A. E. Surkus, K. Junge and M. Beller, ACS Catal. 7 (2017) 1526.
[22] G. M. Ziarani, S. Rohani, A. Ziarati and A. Badiei, RSC Adv. 8 (2018) 41048.
[23] H.Yang, X. Zhang, H. Zou, Z.Yu, S. Li, J. Sun and J. Ma, ACS Sustain.Chem. Eng. 6 (2018) 7918.
[24] X. Qiu, J.Chen, X. Zou, R. Fang, L.Chen, Z. Chen and Y. Li, Chem. Sci. 9 (2018) 8962.
[25] M. Tavassoli, A. Landarani-Isfahani, M. Moghadam, S. Tangestaninejad, V. Mirkhani and I. Mohammadpoor-Baltork, Appl. Catal. A, 503 (2015) 186.
[26] F. Esnaashari, M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor-Baltork A. R. Khosoropour, M. Zakeri and S. Hushmandrad, Polyhedron, 48 (2012) 212.
[27] M. Nooraeipour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork and N. Iravani, J. Coord. Chem. 65 (2012) 226.
[28] M. Zakeri, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, A. R. Khosropour, and M. Alizadeh, Transit. Met. Chem. 37 (2012) 45.
[29] M. Duss, J. J. Vallooran, L. Salvati Manni, N. Kieliger, S. Handschin, R. Mezzenga and E. M. Landau, Langmuir, 35 (2018) 120.
[30] K. Thakur and B. Kandasubramanian, J. Chem. Eng. Data. 64 (2019) 833.
[31] D. Khalili, A. R. Banazadeh and E. Etemadi-Davan, Catal. Lett. 147 (2017) 2674.
[32] F. Zadehahmadi, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, A. R. Khosropour and R. Kardanpour, Appl. Catal. A, 477 (2014) 34.
[33] A. Keivanloo, M. Gholizadeh and A. Rzai, J. Of Applied Chemistry, 54 (1399) 71, in Persian.
[34] A. Bezaatpour, N. Bozari and S. Khatami, J. Of Applied Chemistry, 50 (1398) 55, in Persian.
[35] S. sajjadifar, Z. arzehgar and S. rezayati, J. Of Applied Chemistry, 51 (1398) 213, in Persian.
[36] F. Zadehahmadi, F. Ahmadi, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork and R. Kardanpour, J. Mol. Catal. A: Chem. 398 (2015) 1.
[37] C. Su and K. P. Loh, Acc. Chem. Res.46 (2012) 2275.
[38] C. K. Chua and M. Pumera, Chem. Soc. Rev. 43 (2014) 291.
[39] S. Navalon, A. Dhakshinamoorthy, M. Alvaro and H. Garcia, Chem. Rev. 114 (2014) 6179.
[40] V. Georgakilas, M. Otyepka, A. B. Bourlinos, V. Chandra, N. Kim, K. C. Kemp and K. S. Kim,Chem. Rev. 112 (2012) 6156.
[41] D. W. Boukhvalov and M. I. Katsnelson, J. Condens. Matter Phys. 21 (2009) 344205.
[42] W. S. Hummers Jr and R. E. Offeman, J. Am. Chem. Soc. 80 (1958) 1339.
[43] H. P. Mungs, S. Verma. N. Kumar. B, Sain, and O. P. Khatri. J. Mater. Chem. 22 (2012) 5427.
[44] P. Kumar, G. Singh, T. Deependra and L. J. Suman, RSC Adv. 4 (2014) 50331.
[45] G. Venugopal, M. H. Jung, M. S. Suemitsu and J. Kim, Carbon, 49 (2011) 2766.
[46] A. C. Ferrari, J. C. Meyer, V. C. Scardaci, M. Casiraghi, F. Lazzeri, S. Mauri, D. Piscanec, K. S. Jiang, S. Roth and A. K. Geim, Phys. Rev. Lett. 97 (2006) 187401.
[47] Z. Li, S. Wu, Y. Ma, H. Liu, J. Hu, L. Liu, Q. Huo, J. Guan and Q. Kan, Transit. Met. Chem. 38 (2013) 243.
[48] Z. Li, H. Ding, S. Wu, H. Liu, H. Su, J. Sun, D. Zheng, Q. Huo, J. Guan and Q. Kan, Mater. Res. Bull. 48 (2013) 1920.
[49] A. Modaka, M. Nandi and A. Bhaumik. Catal. Today, 198 (2012) 45.
[50] G. Grivani, A. D. Khalaji, V. Tahmasebi, K. Gotoh and H. Ishida, Polyhedron, 31 (2012) 265.
[51] Z. Li, S. Wu, D. Zheng, J. Liu, H. Liu, H. Lu and Q. Kan, Appl. Organomet. Chem. 28 (2014) 317.
[52] Q. Zhao, C. Bai, W. Zhang, Y. Li, G. Zhang, F. Zhang and X. Fan, Ind. Eng. Chem. Res. 53 (2014) 4232.
[53] M. Masteri-Farahani and S. Mirshekar, Colloids Surf. A, 538 (2018) 387.
[54] G. Bian, P. Jiang, F. Wang, Y. Shen, K. Jiang, L. Liu and W. Zhang, New J. Chem. 42 (2018) 85.
[55] A. Zarnegaryan, M. Moghadam, S. Tangestaninejad, V. Mirkhani and I. Mohammadpoor-Baltork, New J. Chem. 40 (2016) 2280.