Chinese Journal of Organic Chemistry >
Synthesis of 5-Hydroxymethylfurfural from Sucrose Catalyzed by Phosphotungstate
Received date: 2017-09-05
Revised date: 2017-11-08
Online published: 2017-11-21
Supported by
Project supported by the National Natural Science Foundation of China (No. 21476021)
5-Hydroxymethylfurfural (5-HMF) is one of the most important biomass-derived platform compounds and can be used to produce various chemicals. The synthesis of 5-hydroxymethylfurfural (5-HMF) from sucrose catalyzed by a variety of phosphotungstate (Nb0.6PW12O40, Sn0.75PW12O40, CrPW12O40, CePW12O40) has been studied, and the catalysts are characterized by FTIR, XRD, UV-Vis, TGA, NH3-TPD and NMR. The optimum yield of 5-HMF reached 62.54% with 99.3% conversion of sucrose, using Nb0.6PW12O40 in dimethyl sulfoxide (DMSO) at 80℃ under 0.1 MPa of N2 with reaction time of 90 min. Moreover, Nb0.6PW12O40 could be reused five times without loss of activity, and the reaction mechanism was proposed. This study has reference significance for carbohydrate conversion to 5-HMF.
Key words： 5-hydroxymethylfurfural; sucrose; phosphotungstate
Qiu Guo , Wang Xincheng , Huang Chongpin , Zhang Pu , Li Yingxia , Chen Biaohua . Synthesis of 5-Hydroxymethylfurfural from Sucrose Catalyzed by Phosphotungstate[J]. Chinese Journal of Organic Chemistry, 2018 , 38(4) : 940 -948 . DOI: 10.6023/cjoc201709007
[1] Zhang, X.; Wilson, K.; Lee, A. F. Chem. Rev. 2016, 116, 12328.
[2] Zhang, X. D.; Xu, M.; Sun, R. F. J. Fuel Chem. Technol. 2006, 34, 123(in Chinese). (张晓东, 许敏, 孙荣峰, 燃料化学学报, 2006, 34, 123.)
[3] Bhanja, P.; Bhaumik, A. Fuel 2016, 185, 432.
[4] Wang, H.; Liu, S.; Zhao, Y.; Zhang, H.; Wang, J. ACS. Sustainable Chem. Eng. 2016, 4, 6712.
[5] And, F. S. A.; Yoshida, H. Ind. Eng. Chem. Res. 2007, 46, 7703.
[6] And, F. S. A.; Yoshida, H. Ind. Eng. Chem. Res. 2006, 45, 2163.
[7] Carniti, P.; Gervasini, A.; Bossola, F.; Dal Santo, V. Appl. Catal. B 2016, 193, 93.
[8] Xu, Z. L.; Wang, X. Y.; Shen, M. Y.; Du, C. H. Chem. Pap. 2016, 70, 1649.
[9] Li, W.; Xu, Z.; Zhang, T.; Li, G.; Jameel, H.; Chang, H. M.; Ma, L. BioResources 2016, 11, 5839.
[10] Qu, Y.; Huang, C.; Song, Y.; Zhang, J.; Chen, B. Bioresour. Technol. 2012, 121, 463.
[11] Moreno-Recio, M.; Santamarla-Gonzalez, J.; Maireles-Torres, P. Chem. Eng. J. 2016, 303, 22.
[12] Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L. Ind. Eng. Chem. Res. 2008, 47, 9234.
[13] Sun, C. L. Ph.D. Dissertation, Qingdao University of Science and Technology, Qingdao, 2011(in Chinese). (孙春蕾, 博士论文, 青岛科技大学, 青岛, 2011.)
[14] Gomes, F. N. D. C.; Mendes, F. M. T.; Souza, M. M. V. M. Catal. Today 2017, 279, 296.
[15] Qu, Y. S.; Huang, C. P.; Song, Y. L.; Zhang, J.; Chen, B. H. J. Beijing Univ. Chem. Technol. (Nat. Sci. Ed.) 2012, 39, 12(in Chinese). (曲永水, 黄崇品, 宋彦磊, 张傑, 陈标华, 北京化工大学学报(自然科学版), 2012, 39, 12.)
[16] Liu, X. Y.; Qiu, J. J.; Zhou, Y. H.; Qu, J. P. Fine. Chem. 2012, 29, 31(in Chinese). (刘欣颖, 邱俊杰, 周宇涵, 曲丽红, 曲景平, 精细化工, 2012, 29, 31.)
[17] Zhou, M. M.S. Thesis, Zhejiang Normal University, Hangzhou, 2015(in Chinese). (邹敏, 硕士论文, 浙江师范大学, 杭州, 2015.)
[18] Qu, Y. S. Ph.D. Dissertation, Beijing University of Chemical Technology, Beijing, 2012(in Chinese). (曲永水, 博士论文, 北京化工大学, 北京, 2012.)
[19] Wang, C. M.S. Thesis, Tianjin University, Tianjin, 2012(in Chinese). (王超, 硕士论文, 天津大学, 天津, 2012.)
[20] Carlini, C.; Giuttari, M.; Galletti, A. M. R.; Sbrana, G.; Armaroli, T.; Busca, G. Appl. Catal. A-Gen. 1999, 183, 295.
[21] Kreissl, H. T.; Nakagawa, K.; Peng, Y.-K.; Koito, Y.; Zheng, J.; Tsang, S. C. E. J. Catal. 2016, 338, 329.
[22] Zhang, X.; Zhang, D.; Sun, Z.; Xue, L.; Wang, X.; Jiang, Z. Appl. Catal. B 2016, 196, 50.
[23] Cao, X. H.; Ren, J.; Zhan, C. C.; Xu, C. L.; Xie, B. H.; Yan, P. J. Funct. Mater. 2013, 44, 1736(in Chinese). (曹小华, 任杰, 占昌朝, 徐常龙, 谢宝华, 严平, 功能材料, 2013, 44, 1736.)
[24] Liu, Y. M.S. Thesis, Xiangtan University, Xiangtan, 2012 (in Chinese). (刘媛, 硕士论文, 湘潭大学, 湘潭, 2012.)
[25] Ren, Y.; Liu, B.; Zhang, Z.; Lin, J. J. Ind. Eng. Chem. 2015, 21, 1127.
[26] Wang, E. B.; Hu, C. W.; Xu, L. Introduction of Polyacid Chemistry, Chemical Industry Press, Beijing, 1998 (in Chinese). (王恩波, 胡长文, 许林, 多酸化学导论, 化学工业出版社, 北京, 1998.)
[27] Wang, G. P.; Chou, W.; Ren, C. J.; Chai, J. J.; Dong, W.; Chen, Y. L.; Gong, M. C. Chin. J. Catal. 2009, 30, 913(in Chinese). (王光平, 仇伟, 任成军, 柴军军, 董伟, 陈耀强, 龚茂初, 催化学报, 2009, 30, 913.)
[28] Hidalgo, C. V.; Itoh, H.; Hattori, T.; Niwa, M.; Murakami, Y. J. Catal. 1984, 85, 362.
[29] van Putten, R.-J.; van der Waal, J. C.; de Jong, E.; Rasrendra, C. B.; Heeres, H. J.; de Vries, J. G. Chem. Rev. 2013, 113, 1499.
[30] Song, Y. L. Ph.D. Dissertation, Beijing University of Chemical Technology, Beijing, 2014(in Chinese). (宋彦磊, 博士论文, 北京化工大学, 北京, 2014.)
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