Catalytic application of a novel nano-catalyst of CuO/MnO2 for the synthesis of propargylamine derivatives

الموضوعات : Iranian Journal of Catalysis

Fatameh Ghadirian ¹ (Department of Chemistry, Faculty of Science, Shahrekord University, Shahrekord, Iran.)
Ahmad Reza Momeni ² (Department of Chemistry, Faculty of Science, Shahrekord University, Shahrekord, Iran.)
Jalal Albadi ³ (Department of Chemistry, Faculty of Science, Shahrekord University, Shahrekord, Iran.)

تاريخ الإرسال : 02 السبت , ذو الحجة, 1440 تاريخ التأكيد : 10 الجمعة , شعبان, 1441 تاريخ الإصدار : 09 الإثنين , شوال, 1441

الکلمات المفتاحية: aldehyde, amine, CuO/MnO2 nanocatalyst, Propargylamine derivatives, Phenylacetylene,

ملخص المقالة :

In the present research, an efficient process for the synthesis of propargylamine derivatives catalyzed by a novel nanocomposite of CuO/MnO2 is reported. CuO/MnO2 nano-catalyst was synthesized by the co-precipitation process and characterized by scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction(XRD), ICP-OES and BET surface area analysis. A broad range of aromatic aldehydes was reacted with amines and phenylacetylene to produce the corresponding propargylamines. The CuO/MnO2 nano-catalyst is recyclable up to 7 repeated runs and it can be easily recovered by simple filtration. The present method affords additional advantages such as straightforward procedure, ease of workup, clean method and moderately short reaction times

المصادر:

[1] A. Dömling, W. Wang, K. Wang, Chem. Rev. 112 (2012) 3083-3135.
[2] V.A. Peshkov, O.P. Pereshivko, E.V. Van der Eycken, Chem. Soc. Rev. 41 (2012) 3790-3807.
[3] B. Yan, Y. Liu, Org. Lett. 9 (2007) 4323-4326.
[4] B.M. Trost, C.K. Chung, A.B. Pinkerton, Angew. Chem. Int. Ed. 43 (2004) 4327-4329.
[5] Z. Sotoudehnia, J. Albadi, A.R. Momeni, Appl. Organomet. Chem. 33 (2018) e4625.
[6] A. Feiz, A. Bazgir, Catal. Commun. 73 (2016) 88-92.
[7] A.V. Nakhate, Yadav, Mol. Catal. 451 (2018) 209-219.
[8] R. Manikandan, P. Anitha, P. Viswanathamurthi, J.G. Malecki, Polyhedron 119 (2016) 300-306.
[9] S.J. Borah, D.K. Das, Catal. Lett. 146 (2016) 656-665.
[10] J. Safaei-Ghomi, S.H. Nazemzadeh, Catal. Lett. 147 (2017) 1696-1703.
[11] D.A. Kotadia, S.S. Soni, Appl. Catal. A 488 (2014) 231-238.
[12] R. Sasikala, B. Subash, K. Jayamoorthy, S. Kutti Rani, Silicon, 10 (2018) 1095-1101.
[13] M. Mirabedini, E. Motamedi, M.Z. Kassaee, Chin. Chem. Lett. 26 (2015) 1085-1090.
[14] J. Safaei-Ghomi, S.H. Nazemzadeh, H. Shahbazi-Alavi, Res. Chem. Intermed. 43 (2017) 7375-7386.
[15] W.-J. Sun, F.‐G. Xi, W.‐L. Pan, E.‐Q. Gao, Mol. Catal. 430 (2017) 36-42.
[16] K.V.V. Satyanarayana, P. AtchutaRamiah, Y.L.N. Murty, M. Ravi Chandra, S.V.N. Pammi, Catal. Commun. 25 (2012) 50-53.
[17] J. Pal, C. Mondal, A. Kumar Sasmal, M. Ganguly, Y. Negishi, T. Pal, ACS Appl. Mater. Interfaces 6 (2014) 9173-9184.
[18] K. Qian, Z. Qian, Q, Hua, Z. Jiang, W. Huang, Appl. Surf. Sci. 273 (2013) 357-363.
[19] M.J. Angeles-Hernandez, G.A. Leeke, R.C.D. Santos, Ind. Eng. Chem. Res. 48 (2009) 1208-1214.
[20] A. Martin, U. Armbruster, M. Schneider, J. Radnik, M.-M. Pohl, J. Mater. Chem. 12 (2002) 639-645.
[21] A. Khan, Z. Liao, Y. Liu, A. Jawad, L. Ifthikar, Z. Chen, J. Hazard. Mater. 329 (2017) 262-271.
[22] J. Albadi, A. Alihosseinzadeh, M. Jalali, M. Shahrezaie, A. Mansournezhad, Mol. Catal. 440 (2017)133-139.
[23] J. Albadi, M. Jalali, H.A. Samimi, Catal. Lett. 148 (2018) 3750-3756.
[24] J. Albadi, A. Mansournezhad, Iran. J. Catal. 3 (2013) 73-77.
[25] J.Albadi, N. Iravani, M. Khoshakhlagh, Iran. J. Catal. 2 (2012) 85-89.
[26] J. Albadi, M. Jalali, A. Momeni, Res. Chem. Intermed. 44 (2018) 2395-2404.
[27] M. M. Thackeray, Prog. Solid State Chem. 25 (1997) 1-71.
[28] P. Strobel, F. Thiery, C. Darie, O. Proux, A. Ibarra-Palos, M. Bacia, J.B. Soupart, J. Mater. Chem. 15 (2005) 4799-4808.
[29] F.Y. Cheng, J.Z. Zhao, W.E. Song, C.S. Li, H. Ma, J. Chen, P.W. Shen, Inorg. Chem. 45(2006) 2038-2044.
[30] X.K. Huang, D.P. Lv, H.J. Yue, A. Attia, Y. Yang, Nanotechnology 19 (2008) 225606-225612.
[31] T. Zhang, D. Wang, Z. Gao, K. Zhao, Y. Gu, Y. Zhang, D. He, RSC Adv. 6 (2016) 70261-70270.
[32] C.L. Chiang, K.S. Lin, Int. J. Hydrogen Energy 42 (2017) 23526-23538.
[33] Y. Hasegawa, K. Fukumoto, T. Ishima, H. Yamamoto, M. Sano, T. Miyake, Appl. Catal. B 89 (2009) 420-424.
[34] A.J. Roberts, R.C.T. Slade, Electrochim. Acta 55 (2010) 7460-7469.
[35] Y.L. Li, L.H. Li, G.W. Chu, X.F. Zeng, J.F. Chen, L. Shao, Int. J. Electrochem. Sci. 11 (2016) 9644-9655.
[36] C.H. Wang, H.C. Hsu, J.H. Hu, J. Power Sources 249 (2014) 1-8.