Citation: 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 shu

Synthesis of 5-Hydroxymethylfurfural from Sucrose Catalyzed by Phosphotungstate

a.
State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029
b.
Beijing Key Laboratory of Fuels Cleaning and Advanced Catalytic Emission Reduction Technology, Beijing Institute of Petrochemical Technology, Beijing 102617

Corresponding author: Huang Chongpin, huangcp@mail.buct.edu.cn
Received Date: 5 September 2017
Revised Date: 8 November 2017
Available Online: 21 April 2017
Fund Project: the National Natural Science Foundation of China 21476021Project supported by the National Natural Science Foundation of China (No. 21476021)

Figures(16)

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 (Nb_0.6PW₁₂O₄₀, Sn_0.75PW₁₂O₄₀, 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 Nb_0.6PW₁₂O₄₀ in dimethyl sulfoxide (DMSO) at 80℃ under 0.1 MPa of N₂ with reaction time of 90 min. Moreover, Nb_0.6PW₁₂O₄₀ 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 .
- 5-hydroxymethylfurfural,
- sucrose,
- phosphotungstate
1. [1]
  Zhang, X.; Wilson, K.; Lee, A. F. Chem. Rev. 2016, 116, 12328. doi: 10.1021/acs.chemrev.6b00311
2. [2]
  Zhang, X. D.; Xu, M.; Sun, R. F. J. Fuel Chem. Technol. 2006, 34, 123(in Chinese). doi: 10.3969/j.issn.0253-2409.2006.01.027
3. [3]
  Bhanja, P.; Bhaumik, A. Fuel 2016, 185, 432. doi: 10.1016/j.fuel.2016.08.004
4. [4]
  Wang, H.; Liu, S.; Zhao, Y.; Zhang, H.; Wang, J. ACS. Sustainable Chem. Eng. 2016, 4, 6712. doi: 10.1021/acssuschemeng.6b01652
5. [5]
  And, F. S. A.; Yoshida, H. Ind. Eng. Chem. Res. 2007, 46, 7703. doi: 10.1021/ie061673e
6. [6]
  And, F. S. A.; Yoshida, H. Ind. Eng. Chem. Res. 2006, 45, 2163. doi: 10.1021/ie051088y
7. [7]
  Carniti, P.; Gervasini, A.; Bossola, F.; Dal Santo, V. Appl. Catal. B 2016, 193, 93. doi: 10.1016/j.apcatb.2016.04.012
8. [8]
  Xu, Z. L.; Wang, X. Y.; Shen, M. Y.; Du, C. H. Chem. Pap. 2016, 70, 1649.
9. [9]
  Li, W.; Xu, Z.; Zhang, T.; Li, G.; Jameel, H.; Chang, H. M.; Ma, L. BioResources 2016, 11, 5839.
10. [10]
  Qu, Y.; Huang, C.; Song, Y.; Zhang, J.; Chen, B. Bioresour. Technol. 2012, 121, 463.
11. [11]
  Moreno-Recio, M.; Santamaría-González, J.; Maireles-Torres, P. Chem. Eng. J. 2016, 303, 22. doi: 10.1016/j.cej.2016.05.120
12. [12]
  Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L. Ind. Eng. Chem. Res. 2008, 47, 9234. doi: 10.1021/ie801016s
13. [13]
  Sun, C. L. Ph. D. Dissertation, Qingdao University of Science and Technology, Qingdao, 2011(in Chinese).
14. [14]
  Gomes, F. N. D. C.; Mendes, F. M. T.; Souza, M. M. V. M. Catal. Today 2017, 279, 296. doi: 10.1016/j.cattod.2016.02.018
15. [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).
16. [16]
  Liu, X. Y. ; Qiu, J. J. ; Zhou, Y. H. ; Qu, J. P. Fine. Chem. 2012, 29, 31(in Chinese).
17. [17]
  Zhou, M. M. S. Thesis, Zhejiang Normal University, Hangzhou, 2015(in Chinese).
18. [18]
  Qu, Y. S. Ph. D. Dissertation, Beijing University of Chemical Technology, Beijing, 2012(in Chinese).
19. [19]
  Wang, C. M. S. Thesis, Tianjin University, Tianjin, 2012(in Chinese).
20. [20]
  Carlini, C.; Giuttari, M.; Galletti, A. M. R.; Sbrana, G.; Armaroli, T.; Busca, G. Appl. Catal. A-Gen. 1999, 183, 295. doi: 10.1016/S0926-860X(99)00064-2
21. [21]
  Kreissl, H. T.; Nakagawa, K.; Peng, Y.-K.; Koito, Y.; Zheng, J.; Tsang, S. C. E. J. Catal. 2016, 338, 329. doi: 10.1016/j.jcat.2016.03.007
22. [22]
  Zhang, X.; Zhang, D.; Sun, Z.; Xue, L.; Wang, X.; Jiang, Z. Appl. Catal. B 2016, 196, 50. doi: 10.1016/j.apcatb.2016.05.019
23. [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). doi: 10.3969/j.issn.1001-9731.2013.12.014
24. [24]
  Liu, Y. M. S. Thesis, Xiangtan University, Xiangtan, 2012 (in Chinese).
25. [25]
  Ren, Y.; Liu, B.; Zhang, Z.; Lin, J. J. Ind. Eng. Chem. 2015, 21, 1127. doi: 10.1016/j.jiec.2014.05.024
26. [26]
  Wang, E. B.; Hu, C. W.; Xu, L. Introduction of Polyacid Chemistry, Chemical Industry Press, Beijing, 1998 (in Chinese).
27. [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). doi: 10.3321/j.issn:0253-9837.2009.09.012
28. [28]
  Hidalgo, C. V.; Itoh, H.; Hattori, T.; Niwa, M.; Murakami, Y. J. Catal. 1984, 85, 362. doi: 10.1016/0021-9517(84)90225-2
29. [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. doi: 10.1021/cr300182k
30. [30]
  Song, Y. L. Ph. D. Dissertation, Beijing University of Chemical Technology, Beijing, 2014(in Chinese).
1. [1]
  Meiran Li , Yingjie Song , Xin Wan , Yang Li , Yiqi Luo , Yeheng He , Bowen Xia , Hua Zhou , Mingfei Shao . Nickel-Vanadium Layered Double Hydroxides for Efficient and Scalable Electrooxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Generation. Acta Physico-Chimica Sinica, 2024, 40(9): 2306007-0. doi: 10.3866/PKU.WHXB202306007
2. [2]
  Ze Luo , Yukun Zhu , Yadan Luo , Guangmin Ren , Yonghong Wang , Hua Tang . Photocatalytic selective oxidation of 5-hydroxymethylfurfural coupled with H₂ evolution over In₂O₃/ZnIn₂S₄ S-scheme heterojunction. Acta Physico-Chimica Sinica, 2026, 42(3): 100166-0. doi: 10.1016/j.actphy.2025.100166
3. [3]
  Yeyun Zhang , Zhenfeng Shang , Ling Fan . Green experimental improvement and ideological and political teaching design of the acid-catalyzed sucrose hydrolysis. University Chemistry, 2026, 41(6): 353-361. doi: 10.12461/PKU.DXHX202504040
4. [4]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
5. [5]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
6. [6]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
7. [7]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
8. [8]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
9. [9]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
10. [10]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
11. [11]
  Zhongbin Pan , Shijie Huang , Yunjie Luo , Hongzhen Xie . Design of a Comprehensive Experiment for Determining Permanganate Index (COD_Mn) in Drinking Water. University Chemistry, 2024, 39(7): 354-360. doi: 10.12461/PKU.DXHX202311040
12. [12]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
13. [13]
  Yuchen ZHANG , Jingliang LIU , Xiaobo WANG , Jingjing CAO , Jingya SUN . Degradation of tannic acid on activation of peroxymonosulfate mediated by β-MnO₂. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1505-1512. doi: 10.11862/CJIC.20260003
14. [14]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-0. doi: 10.3866/PKU.WHXB202312010
15. [15]
  Yanqin Wang , Kang Wang , Chen Sun , Zhexi Yang . Comprehensive Experiment of Materials Chemistry: Directional Conversion of Urea to Nitrite by Electrochemical Method. University Chemistry, 2026, 41(6): 415-424. doi: 10.12461/PKU.DXHX202603025
16. [16]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . Construction of 4-Amino-1H-imidazole-5-carbonitrile Modified Carbon Nitride-Based Donor-Acceptor Photocatalyst for Efficient Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-0. doi: 10.3866/PKU.WHXB202406026
17. [17]
  Haolin Yang , Aoxiang Fan , Yi Song , Yang Chen . 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验. University Chemistry, 2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156
18. [18]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
19. [19]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
20. [20]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081

Get Citation

PDF

XML

Metrics

PDF Downloads(27)
Abstract views(4910)
HTML views(1726)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142