Abstract
The present paper describes the preparation and characterization of Cu(II) Schiff base complex immobilized onto graphene oxide. The structural and morphological characterization of the heterogeneous catalyst was carried out by different techniques such as Fourier transform infrared and diffuse reflectance UV–Vis spectroscopies, X-ray diffraction, thermogravimetric analysis, nitrogen adsorption–desorption, transmission electron microscopy, field emission scanning electron microscopy and inductively coupled plasma atomic emission spectroscopy. The catalytic activity of the heterogeneous catalyst was studied in the epoxidation of various alkenes using tert-butyl hydroperoxide as an oxidant and it showed high selectivity and catalytic reactivity. The graphene-bound copper Schiff base was successfully reused for several runs without significant loss in its catalytic activity.
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References
R.A. Sheldon, J.K. Kochi, Metal-Catalysed Oxidations of Organic Compounds (Academic Press, New York, 1981)
Q.H. Xia, H.Q. Ge, C.P. Ye, Z.M. Liu, K.-X. Su, Chem. Rev. 105, 1603 (2005)
B. Qi, X.H. Lu, D. Zhou, Q.H. Xia, Z.R. Tang, S.Y. Fang, Y.L. Dong, J. Mol. Catal. A Chem. 322, 73 (2010)
D.E. De Vos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev. 102, 3615 (2002)
P. Roy, M. Nandi, M. Manassero, M. Ricco, M. Mazzani, A. Bhaumik, P. Banerjee, Dalton Trans. 43, 9543 (2009)
M. Torki, S. Tangestaninejad, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork. Appl. Organomet. Chem. 28, 304 (2014)
M. Yadegari, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, Polyhedron 31, 332 (2012)
B. Bahramian, V. Mirkhani, M. Moghadam, S. Tangestaninejad, Catal. Commun. 7, 289 (2006)
V. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, A. Mallekpoor-Shalamzari, Appl. Catal. A Gen. 321, 49 (2007)
S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, K. Ghani, Catal. Commun. 10, 853 (2009)
S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, M.S. Saeedi, Appl. Catal. A Gen. 381, 233 (2010)
M. Zakeri, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, A.R. Khosrpour, M. Alizadeh, Transit. Met. Chem. 37, 45 (2012)
W.R. Lazar. Thiel, A.P. Singh, RSC Adv. 4, 14063 (2014)
A. Bezaatpour, S. Khatami, M. Amiri, RSC Adv. 6, 27452 (2016)
M. Jafarpour, H. Kargar, A. Rezaeifard, RSC Adv. 6, 79085 (2016)
M. Asadniaye Fardjahromi, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, RSC Adv., 6, 20128 (2016)
V. Visnja, P. Jana, P. Biserka, A. Dominique, N. Predrag, M. Dubravka, RSC Adv. 6, 36384 (2016)
W. Wang, D. Agustin, R. Poll, J. Mol. Catal. 443, 52 (2017)
K. S.Novoselov, A. K.Geim, S. V.Morozov, D.Jiang, Y.Zhang, S. V.Dubonos, I. V.Grigorieva, A. A.Firsov, Science 306, 666 (2004)
A.K. Geim, K.S. Novoselov, Nat. Mater. 6, 183 (2007)
D.R. Dreyer, S. Park, C.W. Bielawski, R.S. Ruoff, Chem. Soc. Rev. 39, 228 (2010)
S. Park, R.S. Ruoff, Nat. Nanotechnol 4, 217 (2009)
K.P. Loh, Q. Bao, P.K. Ang, J. Yang, J. Mater. Chem. 20, 2277 (2010)
S. Stankovich, D.A. Dikin, G.H.B. Dommett, K.M. Kohlhaas, E.J. Zimney, E.A. Stach, R.D. Piner, S.T. Nguyen, R.S. Ruoff, Nature 442, 282 (2006)
C.H. Lu, H.H. Yang, C.L. Zhu, X. Chen, G.N. Chen, Angew Chem. Int. Ed. 48, 4785 (2009)
Y.H. Hu, H. Wang, B. Hu, ChemSusChem 3, 782 (2010)
J. Pyun, Angew Chem. Int. Ed. 50, 46 (2011)
L. Wang, K. Lee, Y.Y. Sun, M. Lucking, Z. Chen, J.J. Zhao, S.B. Zhang, ACS Nano 3, 2995 (2009)
A. Lerf, H. He, M. Forster, J. Klinowski, J. Phys. Chem. B 102, 4477 (1998)
H.F. Yang, C.S. Shan, F.H. Li, D.X. Han, Q.X. Zhang, L. Niu, Chem. Commun. 26, 3880 (2009)
H.F. Yang, F.H. Li, C.S. Shan, D.X. Han, Q.X. Zhang, L. Niu, A. Ivaska, J. Mater. Chem. 19, 4632 (2009)
D.A. Dikin, S. Stankovich, E.J. Zimney, R.D. Piner, G.H.B. Dommett, G. Evmenenko, S.T. Nguyen, R.S. Ruoff, Nature 448, 457 (2007)
O.C. Compton, S.T. Nguyen, Small 6, 711 (2010)
L. Dong, R.R.S. Gari, Z. Li, M.M. Craig, S. Hou, Carbon 48, 781 (2010)
T.A. Pham, B.C. Choi, Y.T. Jeong, Nanotech 21, 465603 (2010)
M. Moghadam, H. Salavati, Z. Pahlevanneshan, J. Iran. Chem. Soc. 15, 529 (2018)
L. Zhifang, W. Shujie, D. Hong, Z. Dafang, H. Jing, W. Xu, H. Qisheng, G. Jingqi, K. Qiubin, New J. Chem. 37, 1561 (2013)
S. Rayati, E. Khodaei, S. Shokoohi, M. Jafarian, B. Elmi, A. Wojtczak, Inorgan. Chim. Acta 466, 520 (2017)
A. Allahresani, J. Iran. Chem. Soc. 14, 1051 (2017)
A. Zarrinjahan, M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 13, 1509 (2016)
S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, K. Ghani, Iran. Chem. Soc. 5(Supplement 1), S71–S79 (2008)
H.P. Mungse, S. Verma, N. Kumar, B. Sain, O.P. Khatri, J. Mater. Chem. 22, 5427 (2012)
H. Su, Z. Li, Q.I. Guo, J.I. Guang, Q. Kan, RSC Adv. 4, 9990 (2014)
Q. Zhao, C. Bai, W. Zhang, Y. Li, G. Zhang, F. Zhang, X. Fan, Ind. Eng. Chem. Res. 53, 4232 (2014)
W.S. Hummers, R.E. Offeman, J. Am. Chem. Soc. 80, 1339 (1957)
P.K. Pal, S. Chowdhury, P. Purkayastha, D.A. Tocher, D. Datta, Inorg. Chem. Commun. 3, 585 (2000)
M. Lazghab, K. Saleh, P. Guigon, Chem. Eng. Res. Des. 88, 686 (2010)
C. Baleizao, B. Gigante, M.J. Sabater, H. Garcia, Appl. Catal. A Gen. 228, 279 (2002)
B. Jarrais, C. Pereira, A. Rosa Silva, A.P. Carvalho, J. Pires, C. Freire, Polyhedron 28, 994 (2009)
Y. Gao, Y. Zhang, C. Qiu, J. Zhao, Appl. Organomet. Chem. 25, 54 (2011)
D. Nunes, M. Pillinger, A.A. Valente, I.S. Goncalves, J. Rocha, P. Ferreira, F.E. Kuhn, Eur. J. Inorg. Chem. 2002, 1100
M. Mathesh, J. Liu, N.D. Nam, S.K. Lam, R. Zheng, C.J. Barrow, W. Yang, J. Mater. Chem. C 18, 3084 (2013)
S. Park, K.S. Lee, G. Bozoklu, W. Cai, S.T. Nguyen, R.S. Ruoff, ACS Nano 2, 572 (2008)
P.K. Khatri, S. Choudhary, R. Singh, S.P. Jain, C. Khatri, Dalton Trans. 43, 8054 (2014)
V.H. Pham, T.V. Cuong, S.H. Hur, E.W. Shin, J.S. Kim, J.S. Chung, E.J. Kim, Carbon 48, 1945 (2010)
P. Kumar, G. Singh, D. Tripathi, S.L. Jain, RSC Adv. 4, 50331 (2014)
V. León, M. Quintana, M.A. Herrero, J.L.G. Fierro, A. delaHoz, M. Prato, E. Vázquez, Chem. Commun. 47, 10936 (2011)
H.X. Wang, K.G. Zhou, Y.L. Xie, J. Zeng, N. NaChai, J. Li, H.L. Zhang, Chem. Commun. 47, 5747 (2011)
M.A. Nasseri, A. Allahresani, H. Raissi, RSC Adv. 4, 26087 (2014)
F. Tuinstra, J.L. Koenig, J. Chem. Phys. 53, 1126 (1970)
G. Venugopal, M.H. Jung, M. Suemitsu, S.J. Kim, Carbon 49, 2766 (2011)
A.C. Ferrari, J.C. Meyer, V. Scardaci, C. Casiraghi, M. Lazzeri, F. Mauri, S. Piscanec, D. Jiang, K.S. Novoselov, S. Roth, A.K. Geim, Phys. Rev. Lett. 97, 187401 (2006)
A. Zarnegaryan, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammdpoor-Baltork, New J. Chem. 40, 2280 (2016)
P. Roy, M. Nandi, M. Manassero, M. Ricco´, M. Mazzani, A. Bhaumik, P. Banerjee, Dalton Trans. 43, 9543 (2009)
S. Biswas, A. Dutta, M. Dolai, I. Bhowmick, M. Rouzières, H.M. Lee, R. Clérac, M. Ali, Eur. J. Inorg. Chem. 2013, 4922
S. Rayati, S. Zakavi, M. Koliaei, A. Wojtczak, A. Kozakiewicz, Inorg. Chem. Commun. 13, 203 (2010)
L. Xu, S. Sithambaram, Y. Zhang, C. Chen, L. Jin, R.Joesten and S.L. Suib, Chem. Mater. 21, 1253 (2009)
R. hBera, C. Adhikary, S. Ianelli, S. Chaudhuri, S. Koner, Polyhedron 29, 2166 (2010)
S. Ray, S. Jana, A. Jana, S. Konar, K. Das, S. Chatterjee, R.J. Butcher, S. Kumar Kar, Polyhedron 46, 74 (2012)
M. Nandi, P. Roy, H. Uyamac, A. Bhaumik, Dalton Trans. 40, 12510 (2011)
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The authors are grateful to the Research Council of the University of Isfahan for financial support of this work.
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Zarnegaryan, A., Pahlevanneshan, Z., Moghadam, M. et al. Copper(II) Schiff base complex immobilized on graphene nanosheets: a heterogeneous catalyst for epoxidation of olefins. J IRAN CHEM SOC 16, 747–756 (2019). https://doi.org/10.1007/s13738-018-1552-3
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DOI: https://doi.org/10.1007/s13738-018-1552-3