Citation: ZHU Li-wei, WANG Jian-gang, ZHAO Ping-ping, SONG Feng, SUN Xiu-yu, WANG Li-hong, CUI Hong-you, YI Wei-ming. Preparation of the Nb-P/SBA-15 catalyst and its performance in the dehydration of fructose to 5-hydroxymethylfurfural[J]. Journal of Fuel Chemistry and Technology, ;2017, 45(6): 651-659. shu

Preparation of the Nb-P/SBA-15 catalyst and its performance in the dehydration of fructose to 5-hydroxymethylfurfural

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,
Received Date: 27 February 2017
Revised Date: 12 April 2017

Fund Project: the National Natural Science Foundations of China 51536009National High Technology Research and Development Program of China 2012AA101808National High Technology Research and Development Program of China 863计划the National Natural Science Foundations of China 21506118the National Natural Science Foundations of China 21476132the National Natural Science Foundations of China 51406109

Figures(9)

Dehydration of fructose to 5-hydroxymethylfurfural (5-HMF) is one of the pivotal reactions in conversion of biomass towards valuable platform compounds. In this work, Nb/SBA-15 was prepared via incipient wetness impregnation with self-made SBA-15 as support; Nb/SBA-15 was further treated with phosphoric acid and calcined at 450℃, to obtain the Nb-P/SBA-15 catalyst. The Nb-P/SBA-15 catalyst was characterized by SEM, TEM, BET, XRD and NH₃-TPD; its performance in the dehydration of fructose to 5-HMF was then investigated. The results indicate that the microscopic structure of SBA-15 is well preserved in Nb/SBA-15 with an internal channel diameter of about 10 nm and the niobic species are highly dispersed on the surface of the channels; the wall of channels became thinner after impregnation of Nb and treatment with phosphoric acid. After the treatment with phosphoric acid, the weak acid sites are increased, moreover, the medium and strong acidic sites are generated in Nb-P/SBA-15; as a result, for the dehydration of fructose in a water/MIBK biphasic system, Nb-P/SBA-15 exhibits higher catalytic activity and selectivity to 5-HMF. By reaction at 160℃ for 1.5 h, with a water/MIBK volume ratio of 1/2, the conversion of fructose and the yield of 5-HMF reach 96.1% and 92.6%, respectively. Moreover, the Nb-P/SBA-15 catalyst also exhibits excellent stability in view of water tolerance; it still demonstrates high catalytic activity and selectivity to 5-HMF even after successive recycling for four times.
- niobic acid,
- phosphoric treatment,
- fructose,
- hydration,
- 5-hydroxymethyl furfural (5-HMF),
- Nb-P/SBA-15
1. [1]
  LIN Mu-sen, JIANG Jian-chun. A review on fast pyrolysis of biomass[J]. Biomass Chem Eng, 2006,40(1):21-26.
2. [2]
  RUSSO P A, ANTUNES M A, NEVES P, WIPER P V, FAZIO E, NERI F, BARRECA F, MAFRA L, PILLINGER M, PINNA N, VALENTE A A. Mesoporous carbon-silica solid acid catalysts for producing useful bio-products within the sugar-platform of biorefineries[J]. Green Chem, 2014,16(9):4292-4305. doi: 10.1039/C4GC01037J
3. [3]
  OSATIASHTIANI A, LEE A F, GRANOLLERS M, BROWN D R, OLIVI L, MORALES G, MELERO J A, WILSON K. Hydrothermally stable, conformal, sulfated zirconia monolayer catalysts for glucose conversion to 5-HMF[J]. ACS Catal, 2015,5(7):4345-4352. doi: 10.1021/acscatal.5b00965
4. [4]
  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 Brønsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl)furfural and levulinic acid in aqueous media[J]. J Amer Chem Soc, 2013,135(10):3997-4006. doi: 10.1021/ja3122763
5. [5]
  TAKEUCHI Y, JIN F, TOHJI K, ENOMOTO H. Acid catalytic hydrothermal conversion of carbohydrate biomass into useful substances[J]. J Mate Sci, 2007,43(7):2472-2475.
6. [6]
  SOUZA R L D, YU H, RATABOUL F, ESSAYEM N. 5-hydroxymethylfurfural (5-HMF) production from hexoses:Limits of heterogeneous catalysis in hydrothermal conditions and potential of concentrated aqueous organic acids as reactive solvent system[J]. Challenges, 2012,3(2):212-232. doi: 10.3390/challe3020212
7. [7]
  MORENO-RECIO M, SANTAMARÍA-GONZÁLEZ J, MAIRELES-TORRES P. Brønsted and Lewis acid ZSM-5 zeolites for the catalytic dehydration of glucose into 5-hydroxymethylfurfural[J]. Chem Eng J, 2016,303:22-30. doi: 10.1016/j.cej.2016.05.120
8. [8]
  SARAVANAMURUGAN S, PANIAGUA M, MELERO JA, RⅡSAGER A. Efficient isomerization of glucose to fructose over zeolites in consecutive reactions in alcohol and aqueous media[J]. J Am Chem Soc, 2013,135(14):5246-5249. doi: 10.1021/ja400097f
9. [9]
  CUI M, HUANG R, QI W, SU R, HE Z. Cascade catalysis via dehydration and oxidation:One-pot synthesis of 2, 5-diformylfuran from fructose using acid and V₂O₅/ceramic catalysts[J]. RSC Adv, 2017,7(13):7560-7566. doi: 10.1039/C6RA27678D
10. [10]
  JIMÉNEZ-MORALES I, MORENO-RECIO M, SANTAMARÍA-GONZÁLEZ J, MAIRELES-TORRES P, JIMÉNEZ-LÓPEZ A. Mesoporous tantalum oxide as catalyst for dehydration of glucose to 5-hydroxymethylfurfural[J]. Appl Catal B:Environ, 2014,154-155:190-196. doi: 10.1016/j.apcatb.2014.02.024
11. [11]
  XUE Z, MA MG, LI Z, MU T. Advances in conversion of glucose and cellulose to 5-hydroxymethylfurfural over heterogeneous catalysts[J]. RSC Adv, 2016,6:98874-98892. doi: 10.1039/C6RA20547J
12. [12]
  XIAO Y, SONG Y F. Efficient catalytic conversion of the fructose into 5-hydroxymethylfurfural by heteropolyacids in the ionic liquid of 1-butyl-3-methyl imidazolium chloride[J]. Appl Catal A:Gen, 2014,484:74-78. doi: 10.1016/j.apcata.2014.07.014
13. [13]
  LI Y, LIU H, SONG C, GU X, LI H, ZHU W, YIN S, HAN C. The dehydration of fructose to 5-hydroxymethylfurfural efficiently catalyzed by acidic ion-exchange resin in ionic liquid[J]. Bioresour Technol, 2013,133:347-353. doi: 10.1016/j.biortech.2013.01.038
14. [14]
  SAMPATH G, KANNAN S. Fructose dehydration to 5-hydroxymethylfurfural:Remarkable solvent influence on recyclability of Amberlyst-15 catalyst and regeneration studies[J]. Catal Commun, 2013,37:41-44. doi: 10.1016/j.catcom.2013.03.021
15. [15]
  NAKAJIMA K, BABA Y, NOMA R, KITANO M, KONDO J N, HAYASHI S, HARA M. Nb₂O₅·nH₂O as a heterogeneous catalyst with water-tolerant Lewis acid sites[J]. J Am Chem Soc, 2011,133(12):4224-4227. doi: 10.1021/ja110482r
16. [16]
  MAURER S M, KO E I. ChemInform abstract:Structural and acidic characterization of niobia aerogels[J]. ChemInform, 1992,135(30):125-134.
17. [17]
  RAMANATHAN A, ZHU H, MAHESWARI R, THAPA P S, SUBRAMANIAM B. Comparative study of Nb-incorporated cubic mesoporous silicates as epoxidation catalysts[J]. Ind Eng Chem Res, 2015,54(16):4236-4242. doi: 10.1021/ie504386g
18. [18]
  YANG Z J, LI Y F, WU Q B, REN N, ZHANG Y H, LIU Z P, TANG Y. Layered niobic acid with self-exfoliatable nanosheets and adjustable acidity for catalytic hydration of ethylene oxide[J]. J Catal, 2011,280(2):247-254. doi: 10.1016/j.jcat.2011.03.026
19. [19]
  TURCO R, ARONNE A, CARNITI P, GERVASINI A, MINIERI L, PERNICE P, TESSER R, VITIELLO R, DI SERIO M. Influence of preparation methods and structure of niobium oxide-based catalysts in the epoxidation reaction[J]. Catal Today, 2015,254:99-103. doi: 10.1016/j.cattod.2014.11.033
20. [20]
  SRILATHA K, LINGAIAH N, DEVI BLAP, PRASAD RBN, VENKATESWAR S, PRASAD PSS. Esterification of free fatty acids for biodiesel production over heteropoly tungstate supported on niobia catalysts[J]. Appl Catal A:Gen, 2009,365(1):28-33. doi: 10.1016/j.apcata.2009.05.025
21. [21]
  DE LA CRUZ M H C, ABDEL-REHIM M A, ROCHA A S, DA SILVA J F C, DA COSTA FARO JR A, LACHTER E R. Liquid phase alkylation of anisole by benzyl alcohol catalyzed on alumina-supported niobia[J]. Catal Commun, 2007,8(11):1650-1654. doi: 10.1016/j.catcom.2007.01.019
22. [22]
  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, 2013,368:78-83. doi: 10.1016/j.carres.2012.12.021
23. [23]
  NGEE E L S, GAO Y, CHEN X, LEE T M, HU Z, ZHAO D, YAN N. Sulfated mesoporous niobium oxide catalyzed 5-hydroxymethylfurfural formation from sugars[J]. Ind Eng Chem Res, 2014,53(37):14225-14233. doi: 10.1021/ie501980t
24. [24]
  GAO J L, GAO S, LIU C L, LIU Z T, DONG W S. Synthesis, characterization, and catalytic application of ordered mesoporous carbon-niobium oxide composites[J]. Mate Res Bull, 2014,59(16):131-136.
25. [25]
  GARCÍA-SANCHO C, AGIRREZABAL-TELLERIA I, GVEMEZ MB, MAIRELES-TORRES P. Dehydration of d-xylose to furfural using different supported niobia catalysts[J]. Appl Catal B:Environ, 2014,152-153:1-10. doi: 10.1016/j.apcatb.2014.01.013
26. [26]
  ZHAO D, FENG J, HUO Q, MELOSH N, FREDRICKSON G H, CHMELKA B F, STUCKY G D. Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores[J]. Science, 1998,279(5350):548-552. doi: 10.1126/science.279.5350.548
27. [27]
  LI Chun-jing, SHEN Jian, ZHANG Liang, WANG Chao. Catalytic synthesis of methyloleate by mesoporous sieve Nb₂O₅/SBA-15[J]. J Liaoning Univ Pet Chem Technol, 2008,28(4):9-15.
28. [28]
  ZHANG Y, WANG J, LI X, LIU X, XIA Y, HU B, LU G, WANG Y. Direct conversion of biomass-derived carbohydrates to 5-hydroxymethylfurural over water-tolerant niobium-based catalysts[J]. Fuel, 2015,139:301-307. doi: 10.1016/j.fuel.2014.08.047
29. [29]
  ORDOMSKY V V, SUSHKEVICH V L, SCHOUTEN J C, VAN DER SCHAAF J, NIJHUIS T A. Glucose dehydration to 5-hydroxymethylfurfural over phosphate catalysts[J]. J Catal, 2013,300(3):37-46.
30. [30]
  HAFIZI H, NAJAFI CHERMAHINI A, SARAJI M, MOHAMMADNEZHAD G. The catalytic conversion of fructose into 5-hydroxymethylfurfural over acid-functionalized KIT-6, an ordered mesoporous silica[J]. Chem Eng J, 2016,294:380-388. doi: 10.1016/j.cej.2016.02.082
31. [31]
  KUO C H, POYRAZ A S, JIN L, MENG Y, PAHALAGEDARA L, CHEN S Y, KRIZ DA, GUILD C, GUDZ A, SUIB S L. Heterogeneous acidic TiO₂ nanoparticles for efficient conversion of biomass derived carbohydrates[J]. Green Chem, 2014,16(2):785-791. doi: 10.1039/c3gc40909k
32. [32]
  LIU Yan-li, WANG Fu-yu, WANG Chong, ZHAO Zhen-bo. WO₃/ZrO₂ for fructose dehydration to 5-hydrocymethylfurfural as a solid acid catalyst[J]. Chem Int Eng Prog, 2014,33(1):105-109.
33. [33]
  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]. J Fuel Chem Technol, 2016,44(11):1341-1347. doi: 10.3969/j.issn.0253-2409.2016.11.010
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