Citation: Qiuhe Ren, Yizheng Huang, Hong Ma, Jin Gao, Jie Xu. Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural promoted by metal halides[J]. Chinese Journal of Catalysis, ;2014, 35(4): 496-500. doi: 10.1016/S1872-2067(14)60012-7 shu

Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural promoted by metal halides

Qiuhe Ren ^a,b ,
Yizheng Huang ^a ,
Hong Ma ^a ,
Jin Gao ^a ,
Jie Xu ^a,,

1.
a Dalian National Laboratory for Clean Energy, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: Jie Xu,
Received Date: 24 November 2013
Available Online: 25 December 2013
Fund Project: 中国科学院知识创新工程重要方向项目(KSCX2-EW-G-5) (KSCX2-EW-G-5)中国科学院战略性先导科技专项-应对气候变化的碳收支认证及相关问题(XDA05010203) (XDA05010203)国家自然科学基金(21233008). (21233008)

The promotion effect of alkali metal halides toward the AlCl₃-catalyzed conversion of glucose to 5-hydroxymethylfurfural (HMF) was investigated. The results show that NaF inhibited the reaction. However, NaI and NaBr promoted the reaction significantly, and the promotion effect of NaI was more obvious than that of NaBr. In N,N-dimethylacetamide (DMAC), when NaI was used as an additive for the AlCl₃-catalyzed conversion of glucose at 130 ℃ for 15 min, glucose conversion increased from 71% to 86%, and the HMF yield increased from 36% to 62%. The AlCl₃-NaI-DMAC system could also be used for the catalytic conversion of other carbohydrates such as fructose, mannose, sucrose, maltose, cellobiose, and inulin to HMF. When sucrose was used as the feedstock, a 63% HMF yield was achieved.
- Carbohydrate,
- 5-Hydroxymethylfurfural,
- Metal halide,
- Catalysis
1. [1]
  [1] Yeh T M, Dickinson J G, Franck A, Linic S, Thompson L T, Savage P E. J Chem Technol Biotechnol, 2013, 88: 13
2. [2]
  [2] Gallezot P. Chem Soc Rev, 2012, 41: 1538
3. [3]
  [3] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588
4. [4]
  [4] 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
5. [5]
  [5] Rosatella A A, Simeonov S P, Frade R F M, Afonso C A M. Green Chem, 2011, 13: 754
6. [6]
  [6] Ma J P, Yu W Q, Wang M, Jia X Q, Lu F, Xu J. Chin J Catal (马继平, 于维强, 王敏, 贾秀全, 路芳, 徐杰. 催化学报), 2013, 34: 492
7. [7]
  [7] Nie J F, Xie J H, Liu H C. Chin J Catal (聂俊芳, 解佳翰, 刘海超. 催化学报), 2013, 34: 871
8. [8]
  [8] Du Z T, Ma J P, Wang F, Liu J X, Xu J. Green Chem, 2011, 13: 554
9. [9]
  [9] Ma J P, Du Z T, Xu J, Chu Q H, Pang Y. ChemSusChem, 2011, 4: 51
10. [10]
  [10] Ma J P, Pang Y, Wang M, Xu J, Ma H, Nie X. J Mater Chem, 2012, 22: 3457
11. [11]
  [11] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346
12. [12]
  [12] Ma J P, Yu X F, Xu J, Pang Y. Polymer, 2012, 53: 4145
13. [13]
  [13] Che P H, Lu F, Zhang J J, Huang Y Z, Nie X, Gao J, Xu J. Bioresour Technol, 2012, 119: 433
14. [14]
  [14] Chen J Z, Lu F, Zhang J J, Yu W Q, Wang F, Gao J, Xu J. ChemCatChem, 2013, 5: 2822
15. [15]
  [15] Jia X Q, Ma J P, Che P H, Lu F, Miao H, Gao J, Xu J. J Energy Chem, 2013, 22: 93
16. [16]
  [16] Cai J Y, Ma H, Zhang J J, Song Q, Du Z T, Huang Y Z, Xu J. Chem Eur J, 2013, 19: 14215
17. [17]
  [17] Qi X H, Guo H X, Li L Y, Smith R L. ChemSusChem, 2012, 5: 2215
18. [18]
  [18] Stahlberg T, Fu W J, Woodley J M, Riisager A. ChemSusChem, 2011, 4: 451
19. [19]
  [19] Roman-Leshkov Y, Chheda J N, Dumesic J A. Science, 2006, 312: 1933
20. [20]
  [20] Wang L, Zhang J, Zhu L F, Meng X J, Xiao F S. J Energy Chem, 2013, 22: 241
21. [21]
  [21] Karinen R, Vilonen K, Niemelae M. ChemSusChem, 2011, 4: 1002
22. [22]
  [22] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316: 1597
23. [23]
  [23] Yong G, Zhang Y G, Ying J. Angew Chem Int Ed, 2008, 47: 9345
24. [24]
  [24] Zhang Z H, Wang Q, Xie H B, Liu W J, Zhao Z B. ChemSusChem, 2011, 4: 131
25. [25]
  [25] Hu S Q, Zhang Z F, Song J L, Zhou Y X, Han B X. Green Chem, 2009, 11: 1746
26. [26]
  [26] Beckerle K, Okuda J. J Mol Catal A, 2012, 356: 158
27. [27]
  [27] Rasrendra C B, Soetedjo J N M, Makertihartha I G B N, Adisasmito S, Heeres H J. Top Catal, 2012, 55: 543
28. [28]
  [28] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal Commun, 2009, 10: 1558
29. [29]
  [29] Ren Q H, Huang Y Z, Ma H, Wang F, Gao J, Xu J. Bioresources, 2013, 8: 1563
30. [30]
  [30] Binder J B, Raines R T. J Am Chem Soc, 2009, 131: 1979
31. [31]
  [31] Lewkowski J. Arkivoc, 2001, 2: 17
32. [32]
  [32] Fagnou K, Lautens M. Angew Chem Int Ed, 2002, 41: 26
33. [33]
  [33] Maruoka K, Ooi T. Chem Eur J, 1999, 5: 829
34. [34]
  [34] Duquesnoy E, Castola V, Casanova J. Carbohydr Res, 2008, 343: 893
35. [35]
  [35] Roslund M U, Tähtinen P, Niemitz M, Sjöholm R. Carbohydr Res, 2008, 343: 101
36. [36]
  [36] Horvat J, Klaic B, Metelko B, Sunjic V. Tetrahedron Lett, 1985, 26: 2111
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]
  Xiangyu CHEN , Zhenzhen MIAO , Ligang XU , Guangbao WU , Zhuang LIU , Wenzhen LÜ , Runfeng CHEN . Research progress on low-dimensional organic-inorganic hybrid metal halide optoelectronic materials. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2201-2217. doi: 10.11862/CJIC.20250056
3. [3]
  Tianhao GE , Sirong LU , Zhiyin XIAO , Wei ZHONG . Synthesis of porphyrin-based ionic polymeric materials for catalytic application in CO₂ conversion. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 722-736. doi: 10.11862/CJIC.20250312
4. [4]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
5. [5]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
6. [6]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
7. [7]
  Qingtao CHEN , Xiangdong SHI , Xianghai RAO , Liying JIANG , Chunxiao JIA , Fenghua CHEN . Catalytic and in situ surface-enhanced Raman scattering detection properties of graphene oxide/gold nanorod assembly. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 120-128. doi: 10.11862/CJIC.20250091
8. [8]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
9. [9]
  Yongxin LIU , Xingchen LI , Hongjia LIU , Danni LI , Tao ZHANG , Xi CHEN . Enhancement effect of Fe₃O₄ conversion to MIL-100(Fe) on activation of persulfate for degradation of antibiotic. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2503-2513. doi: 10.11862/CJIC.20250169
10. [10]
  Ting YANG , Jia AN , Jinyu ZHANG , Ruonan FAN , Rong YAN , Xiaoxia JING , Panpan CHANG , Wei YAN . Synergistic enhancement of ion migration and sulfur conversion kinetics in lithium-sulfur batteries by CeO₂/g-C₃N₄. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 519-530. doi: 10.11862/CJIC.20250274
11. [11]
  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
12. [12]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
13. [13]
  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
14. [14]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
15. [15]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
16. [16]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
17. [17]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
18. [18]
  Rui Li , Huan Liu , Yinan Jiao , Shengjian Qin , Jie Meng , Jiayu Song , Rongrong Yan , Hang Su , Hengbin Chen , Zixuan Shang , Jinjin Zhao . Emerging Irreversible and Reversible Ion Migrations in Perovskites. Acta Physico-Chimica Sinica, 2024, 40(11): 2311011-0. doi: 10.3866/PKU.WHXB202311011
19. [19]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
20. [20]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016

Get Citation

PDF

XML

Metrics

PDF Downloads(1255)
Abstract views(3550)
HTML views(393)

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