Citation: WANG Jian-gang, ZHANG Yun-yun, WANG Yong, ZHU Li-wei, CUI Hong-you, YI Wei-ming. Catalytic fructose dehydration to 5-hydroxymethylfurfural over sulfonated carbons with hierarchically ordered pores[J]. Journal of Fuel Chemistry and Technology, ;2016, 44(11): 1341-1348. shu

Catalytic fructose dehydration to 5-hydroxymethylfurfural over sulfonated carbons with hierarchically ordered pores

WANG Jian-gang ¹ ,
ZHANG Yun-yun ¹ ,
WANG Yong ¹ ,
ZHU Li-wei ¹ ,
CUI Hong-you ^1,*,, ,
YI Wei-ming ^2,*,,

1.
School of Chemical Engineering, Shandong University of Technology, Zibo 255049, China
2.
School of Agricultural Engineering and Food Science, Shandong University of Technology, Zibo 255049, China

Corresponding author: CUI Hong-you, cuihy@sdut.edu.cn YI Wei-ming, yiweiming@sdut.edu.cn
Received Date: 4 July 2016
Revised Date: 26 July 2016

Fund Project: The project was supported by the National Natural Science Foundations of China 21476132The project was supported by the National Natural Science Foundations of China 51536009The project was supported by the National Natural Science Foundations of China 51276103

Figures(7)

Sulfonated carbons with hierarchically ordered pores (SCHOP) were prepared by means of dual template self-assembly, carbonization, HF etching, and sulfonation. The effect of carbonization temperature on microstructure of the prepared carbons as well as the SCHOPs were surveyed at 500-700℃. Using fructose dehydration to 5-hydroxymethylfurfural as a probe reaction, catalytic performance of SCHOPs was examined. The results show that SCHOP-500 carbonized at 500℃ exhibits the highest catalytic activity. SEM and TEM characterization as well as N₂ adsorption desorption show that all of the SCHOPs possess hierarchically ordered macropores and mesopores, but high carbonization temperature damages the regularity of carbon materials slightly. FT-IR, EDS and -SO₃H determination confirm that sulfonic acid group could be successfully introduced to carbon materials by sulfonation. However, high carbonization temperature lowers aromaticity of the carbon materials, and as a result leading to low sulfonation degree. Under the catalysis of SCHOP-500, as high as 93.4% of 5-HMF yield with 96.1% fructose conversion rate is achieved after reacting at 130℃ for 20 min, indicating that SCHOP-500 is a highly effective and efficient solid acid catalyst.
- hierarchically ordered,
- sulfonated carbon,
- fructose,
- 5-HMF,
- porous
1. [1]
  CAI H, LI C, WANG A, ZHANG T. Biomass into chemicals:One-pot production of furan-based diols from carbohydrates via tandem reactions[J]. Catal Today, 2014,234(10):59-65.
2. [2]
  KAZI F K, PATEL A D, SERRANO-RUIZ J C, DUMESIC J A, ANEX R P. Techno-economic analysis of dimethylfuran (DMF) and hydroxymethylfurfural (HMF) production from pure fructose in catalytic processes[J]. Chem Eng J, 2011,169(1/3):329-338.
3. [3]
  RAS E J, MAISULS S, HAESAKKERS P, GRUTER G J, ROTHENBERG G. Selective hydrogenation of 5-ethoxymethylfurfural over alumina-supported heterogeneous catalysts[J]. Adv Synth Catal, 2009,351(18):3175-3185. doi: 10.1002/adsc.v351:18
4. [4]
  TONG X, MA Y, LI Y. Biomass into chemicals:Conversion of sugars to furan derivatives by catalytic processes[J]. Appl Catal A:Gen, 2010,385(1/2):1-13.
5. [5]
  SCHUETTE H A, THOMAS R W. Normal valerolaction. Ⅲ. Its preparation by the catalytic reduction of levulinic acid with hydrogen in the presence of platinum oxide[J]. Chem Eur J, 2012,18(17):5256-5260. doi: 10.1002/chem.v18.17
6. [6]
  PEDERSEN A T, RINGBORG R, GROTKJÆR T, PEDERSEN S, WOODLEY J M. Synthesis of 5-hydroxymethylfurfural (HMF) by acid catalyzed dehydration of glucose-fructose mixtures[J]. Chem Eng J, 2015,273(1):455-464.
7. [7]
  ZHANG J, YU X, ZOU F, ZHONG Y, DU N, HUANG X. Room-temperature ionic liquid system converting fructose into 5-hydroxymethylfurfural in high efficiency[J]. ACS Sustainable Chem Eng, 2015,3(12):3338-3345. doi: 10.1021/acssuschemeng.5b01015
8. [8]
  CHOUDHARY V, MUSHRIF S H, HO C, ANDERKO A, NIKOLAKIS V, MARINKOVIC N S, FRENKEL A I, SANDLER S I, VLACHOS D G. Insights into the interplay of Lewis and Bronsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media[J]. J Am Chem Soc, 2013,135(10):3997-4006. doi: 10.1021/ja3122763
9. [9]
  KRUGER J S, NIKOLAKIS V, VLACHOS D G. Aqueous-phase fructose dehydration using Brønsted acid zeolites:Catalytic activity of dissolved aluminosilicate species[J]. Appl Catal A:Gen, 2014,469(2):116-123.
10. [10]
  SAMPATH G, KANNAN S. Fructose dehydration to 5-hydroxymethylfurfural:Remarkable solvent influence on recyclability of Amberlyst-15 catalyst and regeneration studies[J]. Catal Commun, 2013,37(13):41-44.
11. [11]
  WANG F, WU H Z, LIU C L, YANG R Z, DONG W S. Catalytic dehydration of fructose to 5-hydroxymethylfurfural over Nb2O5 catalyst in organic solvent[J]. Carbohydr Res, 2013,368(10):78-83.
12. [12]
  ZAREYEE D, ALIZADEH P, GHANDALI M S, KHALILZADEH M A. Solvent-free acetylation and tetrahydropyranylation of alcohols catalyzed by recyclable sulfonated ordered nanostructured carbon[J]. Chem Pap, 2013,67(7):713-721.
13. [13]
  GALHARDO T S, SIMONE N, GONCALVES M, FIGUEIREDO F C A, MANDELLI D, CARVALHO W A. Preparation of sulfonated carbons from rice husk and their application in catalytic conversion of glycerol[J]. ACS Sustainable Chem Eng, 2013,1(11):1381-1389. doi: 10.1021/sc400117t
14. [14]
  YAN L, LIU N, WANG Y, MACHIDA H, QI X. Production of 5-hydroxymethylfurfural from corn stalk catalyzed by corn stalk-derived carbonaceous solid acid catalyst[J]. Bioresour Technol, 2014,173(22):462-466.
15. [15]
  KARIMI B, MIRZAEI H M, BEHZADNIA H, VALI H. Novel ordered mesoporous carbon based sulfonic acid as an efficient catalyst in the selective dehydration of fructose into 5-HMF:The role of solvent and surface chemistry[J]. ACS Appl Mater Inter, 2015,7(34):19050-19059. doi: 10.1021/acsami.5b03985
16. [16]
  HU L, TANG X, WU Z, LIN L, XU J, XU N, DAI B. Magnetic lignin-derived carbonaceous catalyst for the dehydration of fructose into 5-hydroxymethylfurfural in dimethylsulfoxide[J]. Chem Eng J, 2015,263(2):299-308.
17. [17]
  ZHAO J, ZHOU C, HE C, DAI Y, JIA X, YANG Y. Efficient dehydration of fructose to 5-hydroxymethylfurfural over sulfonated carbon sphere solid acid catalysts[J]. Catal Today, 2015,264(4):123-130.
18. [18]
  ORDOMSKY V V, SCHOUTEN J C, SCHAAF J V D, NIJHUIS T A. Foam supported sulfonated polystyrene as a new acidic material for catalytic reactions[J]. Chem Eng J, 2012,207-208(5):218-225.
19. [19]
  XIA Y, YANG Z, GOU X, ZHU Y. A simple method for the production of highly ordered porous carbon materials with increased hydrogen uptake capacities[J]. Int J Hydrogen Energy, 2013,38(12):5039-5052. doi: 10.1016/j.ijhydene.2013.02.037
20. [20]
  YUN Y S, PARK D J, MIN J J, JIN H J. 3-D ordered bimodal porous carbon/nickel oxide hybrid electrodes for supercapacitors[J]. Synth Met, 2013,177(8):105-109.
21. [21]
  ZHANG T, ZHANG Q, GE J, GOEBL J, SUN M, YAN Y, LIU Y S, CHANG C, GUO J, YIN Y. A self-templated route to hollow silica microspheres[J]. J Phys Chem C, 2008,113(8):3168-3175.
22. [22]
  ZHENG F C, CHEN Q W, HU L, YAN N, KONG X K. Synthesis of sulfonic acid-functionalized Fe₃O₄@C nanoparticles as magnetically recyclable solid acid catalysts for acetalization reaction[J]. Dalton Trans, 2014,43(3):1220-1227. doi: 10.1039/C3DT52098F
23. [23]
  ZHAO Q, WANG X, LIU J, WANG H, ZHANG Y, GAO J, LU Q, ZHOU H. Design and synthesis of three-dimensional hierarchical ordered porous carbons for supercapacitors[J]. Electrochim Acta, 2015,154(4):110-118.
24. [24]
  XUE C, TU B, ZHAO D. Facile fabrication of hierarchically porous carbonaceous monoliths with ordered mesostructure via an organic organic self-assembly[J]. Nano Res, 2009,2(3):242-253. doi: 10.1007/s12274-009-9022-y
25. [25]
  ZHOU W, YOSHINO M, HIDETOSHI KITA H, OKAMOTO K. Carbon molecular sieve membranes derived from phenolic resin with a pendant sulfonic acid group[J]. Ind Eng Chem Res, 2001,40(22):4801-4807. doi: 10.1021/ie010402v
26. [26]
  CEPEDA-JIMENEZ C M, PASTOR-BLAS M M, FERRANDIZ-GOMEZ T P, MARTIN-MARTINNEZ J M. Influence of the styrene content of thermoplastic styrene-butadiene rubbers in the effectiveness of the treatment with sulfuric acid[J]. Int J Adhes Adhes, 2001,21(2):161-172. doi: 10.1016/S0143-7496(00)00048-8
27. [27]
  OKAMURA M, TAKAGAKI A, TODA M, KONDO J N, DOMEN K, TATSUMI T, HARA M, HAYASHI S. Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon[J]. Chem Mater, 2006,18(13):3039-3045. doi: 10.1021/cm0605623
28. [28]
  SHIMIZU K I, UOZUMI R, SATSUMA A. Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods[J]. Catal Commun, 2009,10(14):1849-1853. doi: 10.1016/j.catcom.2009.06.012
29. [29]
  AMARASEKARA A S, WILLIAMS L T D, EBEDE C C. Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 degrees C:An NMR study[J]. Carbohydr Res, 2008,343(18):3021-3024. doi: 10.1016/j.carres.2008.09.008
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沈阳化工大学材料科学与工程学院沈阳 110142

Catalytic fructose dehydration to 5-hydroxymethylfurfural over sulfonated carbons with hierarchically ordered pores

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com