Baeyer-Villiger Oxidation of Ketones with Hydrogen peroxide in the presence of Nano Zinc oxide

Document Type : Original Article

Authors

Abstract

In this work, a new application of nano zinc oxide in Baeyer-Villiger oxidation of ketones with hydrogen peroxide has been introduced. The capability of nano zinc oxide as a heterogeneous catalyst on the basis of of its very small size and large surface area can improve and also promote the Baeyer-Villiger oxidation process. The synthesized nano zinc oxide was characterized by scanning electron microscopy (SEM) and FT-IR. It was found that H2O2/ZnO system showed good efficiency in Baeyer-Villiger oxidation of alicyclic, aliphatic and aromatic ketones to either esters or lactones. The effects of reaction conditions, such as amount of catalyst, reaction temperature, reaction time and different solvents on the catalytic performance of nano ZnO were also investigated. Notably, the process has advantages such as mild reaction conditions, simple operation and good product yield. To the best of our knowledge, use of H2O2/ZnO system in Baeyer-Villiger reactions has never been reported. It should be pointed out that, H2O2 as an environmentally benign oxidant, produces water as the safest by-product.

Keywords

Main Subjects


[1] F. Cavani, K. Raabova, F. Bigi and C. Quarantelli, Chem. Eur. J. 16 (2010) 12962.
[2] A. Cavarzan, A. Scarso, P. R. Sgarbossa, A. Michelin and G. Strukul, Chem. Cat. Chem. 2 (2010) 1296.
[3] G. J. T. Brink, I. W. C. E. Arends and R. A. Sheldon, Chem. Rev. 104 (2004) 4105.
[4] M. Zárraga, V. Salas, A. Miranda, P. Arroyo and C. Paz, Tetrahedron: Asym. 19 (2008) 796.
[5] R. A. Steffen, S. Teixeira, J. Sepulveda, R. Rinaldi and U. Schuchardt, J. Mol. Catal. A: Chem. 287 (2008) 41.
[6] T. Kawabata, N. Fujisaki, T. Shishido, K. Nomura, T. Sano and K. Takehira, J. Mol. Catal. A: Chem. 253 (2006) 279. 
[7] S. Xu, Z. Wang, X. Zhang, X. Zhang and K. Ding, Angew. Chem. 120 (2008) 2882.
[8] R. Bernini, A. Coratti, G. Fabrizi and A. Goggiamani, Tetrahedron Lett. 44 (2003) 8991.
[9] T. W. Kim, J. Y. Hwang, Y. S. Kim, S. H. Joo, S. C. Chang, J. S. Lee, S. Takatsuto and S. K. Kim, Plant Cell 17 (2003) 2397.
[10] R. Llamas, C. Jiménez-Sanchidrián, J. R. Ruiz and React. Kinet. Catal. Lett. 90 (2007) 309.
[11] T. Yakura, T. Kitano, M. Ikeda and J. I. Uenishi, Tetrahedron Lett. 43 (2002) 6925.
[12] Y. F. Li, M. Q. Guo, S. F. Yin, L. Chen, Y. B. Zhou, R. H. Qiu and C. T. Au, Reac. Kinet. Mech. Cat. 109 (2013) 525.
[13] X. Zhang, J. Ye, L. Yu, X. Shi, M. Zhang, Q. Xu, M. Lautens, Adv. Synth. Catal. 357 (2015), 955.
[14] C. G. Piscopo, S. Loebbecke, R. Maggi and G. Startori, Adv. Synth. Catal. 352 (2010) 1625.
[15] C. Chen, J. Peng, B. Li and L. Wang, Catal. Lett. 131 (2009) 618.
[16] M. Renz and B. Meunier, Eur. J. Org. Chem. (1999) 737.
[17] P. Tonto, O. Mekasuwandumrong, S. Phatanasri, V. Pavarajarn and P. Praserthdam, Ceram. Int. 34 (2008) 57.
[18] K. Varaprasad, G. M. Raghavendra, T. Jayaramudu, J. Seo, Carbohydr. Polym. 135 (2016) 349.
[19] L. Hajiaghababaei, Z. Amini and A. Shah Velayati, J. Appl. Chem. 10 (2015) 21.
[20] R. Moradi, H. Arabi and H. Karimi-Maleh, J. Appl. Chem. 9 (2014) 101.
[21] M. Bordbar, B. Khodadadi, N. Mollatayefe and A. Yeganeh-Faal, J. Appl. Chem. 8 (2013) 43.
[22] M. Hosseini-Sarvari and S. Etemad, Tetrahedron 64 (2008) 5519.
[23] M. Javaherian and H. Eskandari Sabzi, Indian J. Chem. 53B (2014) 631.
[24] Z. Lei, G. Ma, L. Wei, Q. Yang and B. Su, Catal. Lett. 124 (2008) 330.
[25] M. Boronat, A. Corma, M. Renz, G. Sastre, P. M. Viruela, Chem. Eur. J. 11 (2005) 6905.
[26] X. Changjiu, L. Min, Z. Bin and S. Xing, Chin. Pet. Process. Petrochem. Tech. 14 (2012) 7.
[27] M. Bučko, A. Schenkmayerová, P. Gemeiner, A. Vikart, M. Mihovilovič and D. I. Lacík, Enzyme. Microb. Technol. 49 (2011) 284.
[28] N. Mora-Diez, S. Keller and J. R. Alvarez-Idaboy, Org. Biomol. Chem. 7 (2009) 3682.
[29] Z. Lei, Q. Zhang, J. Luo and X. He, Tetrahedron Lett. 46 (2005) 3505.
[30] M. Uyanik, D. Nakashima and K. Ishihara, Angew. Chem. Int. Ed. 51 (2012) 9093.
[31] S. I.‎ Murahashi and T. Naota, Tetrahedron Lett. 33 (1992) 7557.
[32] C. Li, J. Wang, Z. Yang, Z. Hu and Z. Lei, Catal. Commun. 8 (2007) 1202.
[33] G. A. Olah, Q. Wang, N. J. Trivedi and G. K. S. Prakash, Synthesis (1991) 739.