Abstract
Cyclohexanone is an important intermediate for the fabrication of synthetic polymers such as Nylon in chemical industry. A green synthesis of cyclohexanone under mild conditions using environmental friendly oxidants and non-precious catalysts is highly desired. Herein, one-dimensional crystalline h-WO3 nanorods have been synthesized via a facile hydrothermal method. The h-WO3 nanorods are assembled by the closely packed and highly aligned thin nanowires with the lengths up to 10 μm and diameters of about 10 nm, growing along the [001] direction. The h-WO3 nanorods are used as the catalyst for the first time in the selective oxidation of cyclohexanol to cyclohexanone by aqueous hydrogen peroxide. The effective catalysis by h-WO3 nanorods remarkably increases the yield of cyclohexanone from 3.1 to 78.6 %, under the mild conditions (80 °C, ambient pressure). With a high recyclability, the h-WO3 nanorods have shown great potentials in green chemistry for the synthesis of cyclohexanone by the catalytic oxidation of cylohexanol.
Graphical Abstract
Similar content being viewed by others
References
Raja R, Sankar G, Thomas JM (1999) J Am Chem Soc 121:11926–11927
Liu L, Li Y, Wei HB, Dong M, Wang JG, Slawin AMZ, Li JP, Dong JX, Morris RE (2009) Angew Chem Int Ed 48:2206–2209
Benadji S, Mazari T, Dermeche L, Salhi N, Cadot E, Rabia C (2013) Catal Lett 143:749–755
Li ZL, Liu JH, Xia CG, Li FW (2013) ACS Catal 3:2440–2448
Liu HZ, Jiang T, Han BX, Liang SG, Zhou YX (2009) Science 326:1250–1252
Wang Y, Yao J, Li HR, Su DS, Antonietti M (2011) J Am Chem Soc 133:2362–2365
Chen L, Zhou T, Chen LF, Ye YM, Qi ZW, Freund H, Sundmacher K (2011) Chem Commun 47:9354–9356
Xu YJ, Landon P, Enache D, Carley AF, Roberts MW, Hutchings GJ (2005) Catal Lett 101:175–179
Chatel G, Monnier C, Kardos N, Voiron C, Andrioletti B, Draye M (2014) Appl Catal A 478:157–164
Supale AR, Gokavi GS (2008) Catal Lett 124:284–287
Figueiredo H, Silva B, Kuźniarska-Biernacka I, Fonseca AM, Medina R, Rasmussen S, Bañares MA, Neves IC, Tavares T (2014) Chem Eng J 247:134–141
Jana SK, Kubota Y, Tatsumi T (2008) J Catal 255(1):40–47
Gao BJ, Zhang LQ, Chen T (2015) Chinese J Catal 36(8):1230–1235
Wang LB, Zhao ST, Liu CX, Li C, Li X, Li HL, Wang YC, Ma C, Li ZY, Zeng J (2015) Nano Lett 15:2875–2880
Durgasri DN, Vinodkumar T, Sudarsanam P, Reddy BM (2014) Catal Lett 144:971–979
Ghosh S, Acharyya SS, Tripathi D, Bal R (2014) J Mater Chem A 2:15726–15733
Ghosh S, Acharyya SS, Adak S, Konathala LNS, Sasaki T, Bal R (2014) Green Chem 16:2826–2834
Zhang H, Han J, Niu XW, Han X, Wei GD, Han W (2011) J Mol Catal A 350:35–39
Xi YJ, Chen ZX, Kiat VGW, Huang L, Cheng HS (2015) Phys Chem Chem Phys 17:9698–9705
Jin RH, Li HX, Deng JF (2001) J Catal 203:75–81
Yang ZH, Zhang YC, Zhang WX, Wang X, Qian YT, Wen XG, Yang SH (2006) J Solid State Chem 179:679–684
Yang ZH, Yang YM, Zhu X, Chen GD, Zhang WX (2014) Ind Eng Chem Res 53:9608–9615
Gu X, Chen L, Ju ZC, Xu HY, Yang J, Qian YT (2013) Adv Funct Mater 23:4049–4056
Wang JM, Khoo E, Lee PS, Ma J (2008) J Phys Chem C 112:14306–14312
Gu ZJ, Li HQ, Zhai TY, Yang WS, Xia YY, Ma Y, Yao JN (2007) J Solid State Chem 180:98–105
Ryu ZY, Zheng JT, Wang MZ, Zhang BJ (1999) Carbon 37:1257–1264
Zhang WX, Wang H, Yang ZH, Wang F (2007) Colloid Surf A 304:60–66
Chang YH, Jiang T, Han BX, Gao L, Zhang R, Liu ZM, Wu WZ (2003) Ind Eng Chem Res 42:6384–6388
Hasan MA, Zaki MI, Pasupulety L, Kumari K (1999) Appl Catal A 181:171–179
Zhou H, Shen YF, Wang JY, Chen X, O’Young CL, Suib SL (1998) J Catal 176:321–328
Usui Y, Sato K (2003) Green Chem 5:373–375
Noyori R, Aoki M, Sato K (2003) Chem Commun 1:1977–1986
Acknowledgments
The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (NSFC Grants: 91534102, 21176054 and 21271058). This work is also supported by Science and Technology Project of Anhui Province (1501021013) and Intelligent Manufacturing Institute of Hefei University of Technology (IMICZ2015104).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Lei Wang and Zhangxian Chen have contributed equally to this work.
Electronic Supplementary Material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, L., Chen, Z., Huang, M. et al. A Green Route to Cyclohexanone: Selective Oxidation of Cyclohexanol Promoted by Non-precious Catalyst of h-WO3 Nanorods. Catal Lett 146, 1283–1290 (2016). https://doi.org/10.1007/s10562-016-1751-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-016-1751-4