Efficient oxidation of cinnamon oil to natural benzaldehyde over β-cyclodextrin-functionalized MWCNTs

doi:10.1016/S1872-2067(16)62543-3

Abstract

Abstract:

We have designed and prepared β-cyclodextrin (β-CD)-functionalized multi-walled nanotubes (MWCNTs-g-CD) for the oxidation of cinnamon oil to natural benzaldehyde under aqueous conditions. The synergistic effect of combining MWCNTs with β-CD led to a remarkable increase in the performance of the MWCNTs-g-CD for the catalytic oxidation of cinnamaldehyde, which exhibited 95% cinnamaldehyde conversion and 85% selectivity to natural benzaldehyde with a short reaction time of 10 min. The MWCNTs-g-CD also exhibited outstanding recyclability with good stability, showing no discernible decrease in their catalytic activity over five reaction cycles.

Key words: β-cyclodextrin, Cinnamon oil, Selective oxidation, Benzaldehyde, Multi-walled carbon nanotube, Synergistic effect

Zujin Yang, Xia Zhang, Yanxiong Fang, Zebao Rui, Hongbing Ji. Efficient oxidation of cinnamon oil to natural benzaldehyde over β-cyclodextrin-functionalized MWCNTs[J]. Chinese Journal of Catalysis, 2016, 37(12): 2086-2097.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(16)62543-3

https://www.cjcatal.com/EN/Y2016/V37/I12/2086

References

[1] F. A. Jury, I. Polaert, L. B. Pierella, L. Estel, Catal. Commun., 2014, 46, 6-10.
[2] R. B. Cang, B. Lu, X. P. Li, R. Niu, J. X. Zhao, Q. H. Cai, Chem. Eng. Sci., 2015, 137, 268-275.
[3] Z. J. Yang, X. Zhang, X. D. Yao, Y. X. Fang, H. R. Chen, H. B. Ji, Tetrahedron, 2016, 72, 1773-1781.
[4] X. C. Zhu, R. W. Shen, L. X. Zhang, Chin. J. Catal., 2014, 35, 1716-1726.
[5] L. Ma, L. Jia, X. F. Guo, L. J. Xiang, Chin. J. Catal., 2014, 35, 108-119.
[6] J. G. Cui, C. S. Wang, J. Q. Ma, X. H. Liao, Chem. World, 2002, 315-317.
[7] A. O. Pittet, R. Muralidhara, A. L. Liberman, US Patent 4683342A, 1987.
[8] H. R. Chen, H. B. Ji, AIChE J., 2010, 56, 466-476.
[9] H. R. Chen, H. B. Ji, X. T. Zhou, L. F. Wang, Tetrahedron, 2010, 66, 9888-9893.
[10] H. R. Chen, H. B. Ji, L. F. Wang, Fine Chem., 2010, 27, 579-583.
[11] H. R. Chen, H. B. Ji, X. T. Zhou, J. Xu, L. F. Wang, Catal. Commun., 2009, 10, 828-832.
[12] G. S. Chen, M. Jiang, Chem. Soc. Rev., 2011, 40, 2254-2266.
[13] G. Crini, Chem. Rev., 2014, 114, 10940-10975.
[14] E. M. M. Del Valle, Process Biochem., 2004, 39, 1033-1046.
[15] K. Takahashi, Chem. Rev., 1998, 98, 2013-2034.
[16] K. Surendra, N. S. Krishnaveni, M. A. Reddy, Y. V. D. Nageswar, K. R. Rao, J. Org. Chem., 2003, 68, 2058-2059.
[17] A. Kumar, V. D. Tripathi, P. Kumar, Green Chem., 2011,13, 51-54.
[18] K. Surendra, N. S. Krishnaveni, V. P. Kumar, R. Sridhar, K. R. Rao, Tetrahedron Lett., 2005, 46, 4581-4583.
[19] N. S. Krishnaveni, K. Surendra, K. Rama Rao, Adv. Synth. Catal., 2004, 346, 346-350.
[20] J. Shankar, K. Karnakar, B. Srinivas, Y. V. D. Nageswar, Tetrahedron Lett., 2010, 51, 3938-3939.
[21] Z. J. Yang, H. Zeng, X. T. Zhou, H. B. Ji, Supramol. Chem., 2013, 25, 233-245.
[22] Z. J. Yang, H. Zeng, X. T. Zhou, H. B. Ji, Tetrahedron, 2012, 68, 5912-5919.
[23] Z. J. Yang, H. G. Jiang, X. T. Zhou, Y. X. Fang, H. B. Ji, Supramol. Chem., 2012, 24, 379-384.
[24] Z. J. Yang, H. B. Ji, Chin. J. Catal., 2014, 35, 590-598.
[25] G. P. Rao, C. Lu, F. Su, Sep. Purif. Technol., 2007, 58, 224-231.
[26] A. Peigney, C. Laurent, E. Flahaut, R. R. Bacsa, A. Rousset, Carbon, 2001, 39, 507-514.
[27] D. Q. Yang, J. F. Rochette, E. Sacher, J. Phys. Chem. B, 2005, 109, 4481-4484.
[28] J. P. Salvetat, J. M. Bonard, N. H. Thomson, A. J. Kulik, L. Forró, W. Benoit, L. Zuppiroli, Appl. Phys. A, 1999, 69, 255-260.
[29] B. Pan, B. S. Xing, Environ. Sci. Technol., 2008, 42, 9005-9013.
[30] C. Lu, Y. L. Chung, K. F. Chang, Water Res., 2005, 39, 1183-1189.
[31] J. Luo, F. Peng, H. Yu, H. J. Wang, W. X. Zheng, ChemCatChem, 2013, 5, 1578-1586.
[32] S. X. Yang, X. Li, W. P. Zhu, J. B. Wang, C. Descorme, Carbon, 2008, 46, 445-452.
[33] Z. K. Zhao, Y. T. Dai, G. F. Ge, G. R. Wang, ChemCatChem, 2015, 7, 1135-1144.
[34] Z. K. Zhao, Y. T. Dai, G. F. Ge, G. R. Wang, AIChE J., 2015, 61, 2543-2561.
[35] J. Luo, F. Peng, H. Yu, H. J. Wang, Chem. Eng. J., 2012, 204-206, 98-106.
[36] J. Luo, H. Yu, H. J. Wang, H. H. Wang, F. Peng, Chem. Eng. J., 2014, 240, 434-442.
[37] Y. X. Zhang, C. L. Chen, L. X. Peng, Z. S. Ma, Y. J. Zhang, H. H. Xia, A. L. Yang, L. Wang, D. S. Su, J. Zhang, Nano Res., 2015, 8, 502-511.
[38] N. G. Sahoo, S. Rana, J. W. Cho, L. Li, S. H. Chan, Prog. Polym. Sci., 2010, 35, 837-867.
[39] H. N. Hareesh, K. U. Minchitha, N. Nagaraju, N. Kathyayini, Chin. J. Catal., 2015, 36, 1825-1836.
[40] C. Gouveia-Caridade, R. Pauliukaite, C. M. A. Brett, Electrochim. Acta., 2008, 53, 6732-6739.
[41] Z. J. Yang, H. B. Ji, ACS Sustain. Chem. Eng., 2013, 1, 1172-1179.
[42] B. Delley, J. Chem. Phys., 1990, 92, 508-517.
[43] H. Q. Dong, Y. Y. Li, J. H. Yu, Y. Y. Song, X. J. Cai, J. Q. Liu, J. M. Zhang, R. C. Ewing, D. Shi, Small, 2013, 9, 446-456.
[44] W. Liu, Z. Shadike, Z. C. Liu, W. Y. Liu, J. Y. Xie, Z. W. Fu, Carbon, 2015, 93, 523-532.
[45] G. Alarcón-Angeles, B. Pérez-López, M. Palomar-Pardave, M. T. Ramírez-Silva, S. Alegret, A. Merkoçi, Carbon, 2008, 46, 898-906.
[46] T. A. Saleh, S. Agarwal, V. K. Gupta, Appl. Catal. B, 2011, 106, 46-53.
[47] A. Z. M. Badruddoza, A. S. H. Tay, P. Y. Tan, K. Hidajat, M. S. Uddin, J. Hazard. Mater., 2011, 185, 1177-1186.
[48] S. P. Zhang, B. Liu, C. Y. Li, W. Chen, Z. J. Yao, D. T. Yao, R. B. Yu, H. O. Song, Chin. Chem. Lett., 2014, 25, 355-358.
[49] M. R. Karim, C. J. Lee, M. S. Lee, J. Polym. Sci. A, 2006, 44, 5283-5290.
[50] D. D. Shao, G. D. Sheng, C. L. Chen, X. K. Wang, M. Nagatsu, Chemosphere, 2010, 79, 679-685.
[51] Z. J. Yang, J. P. Liu, X. D. Yao, Z. B. Rui, H. B. Ji, Sep. Purif. Technol., 2016, 158, 417-421.
[52] J. G. Yu, D. S. Huang, K. L. Huang, H. Yong, Chin. J. Chem., 2011, 29, 893-897.
[53] H. R. Yao, D. E. Richardson, J. Am. Chem. Soc., 2003, 125, 6211-6221.
[54] H. R. Yao, D. E. Richardson, J. Am. Chem. Soc., 2000, 122, 3220-3221.
[55] D. E. Richardson, H. R. Yao, K. M. Frank, D. A. Bennett, J. Am. Chem. Soc., 2000, 122, 1729-1739.
[56] L. Shao, C. Z. Mu, H. P. Du, Z. Czech, H. C. Du, Y. P. Bai, Appl. Surf. Sci., 2011, 258, 1682-1688.
[57] E. S. Alldredge, ?. C. B?descu, N. Bajwa, F. K. Perkins, E. S. Snow, T. L. Reinecke, Phys. Rev. B, 2010, 82, 2951-2957.