Zeolite-promoted transformation of glucose into 5-hydroxymethylfurfural in ionic liquid

Chemical Engineering Journal

Volumn 244, Issue , 2014, Pages 137-144

  Hu, Lei ^a   Wu, Zhen ^a   Xu, Jiaxing ^a   Sun, Yong ^b   Lin, Lu ^b   Liu, Shijie ^c  

^a HUAIYIN NORMAL UNIVERSITY   (China)

^b XIAMEN UNIVERSITY   (China)

^c STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

5 Hydroxymethylfurfural; Glucose; H zeolite; Ionic liquid

Indexed keywords

EID: 84894092901     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.01.057     Document Type: Article

References (66)

1. Román-Leshkov Y., Chheda J.N., Dumesic J.A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312:1933-1937.
2. Zhao H.B., Holladay J.E., Brown H., Zhang Z.C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 2007, 316:1597-1600.
3. Binder J.B., Raines R.T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J. Am. Chem. Soc. 2009, 131:1979-1985.
4. Hu L., Zhao G., Hao W.W., Tang X., Sun Y., Lin L., Liu S.J. Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes. RSC Adv. 2012, 2:11184-11206.
5. Lima S., Antunes M.M., Pillinger M., Valente A.A. Ionic liquids as tools for the acid-catalyzed hydrolysis/dehydration of saccharides to furanic aldehydes. ChemCatChem 2011, 3:1686-1706.
6. Putten R.J., Waal J.C., Jong E., Rasrendra C.B., Heeres H.J., Vries J.G. Hydroxymethylfurfural: a versatile platform chemical made from renewable resources. Chem. Rev. 2013, 113:1499-1597.
7. Perego C., Bianchi D. Biomass upgrading through acid-base catalysis. Chem. Eng. J. 2010, 161:314-322.
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 Brønsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl)furfural and levulinic acid in aqueous media. J. Am. Chem. Soc. 2013, 135:3997-4006.
9. Ordomsky V.V., Schouten J.C., Schaaf J., Nijhuis T.A. Foam supported sulfonated polystyrene as a new acidic material for catalytic reactions. Chem. Eng. J. 2012, 207-208:218-225.
10. Zhang J., Cao Y., Li H.Q., Ma X.B. Kinetic studies on chromium-catalyzed conversion of glucose into 5-hydroxymethylfurfural in alkylimidazolium chloride ionic liquid. Chem. Eng. J. 2014, 237:55-61.
11. Qi X.H., Watanabe M., Aida T.M., Smith R.L. Synergistic conversion of glucose into 5-hydroxymethylfurfural in ionic liquid-water mixtures. Bioresour. Technol. 2012, 109:224-228.
12. Ståhlberg T., Fu W.J., Woodley J.M., Riisager A. Synthesis of 5-(hydroxymethyl)furfural in ionic liquids: paving the way to renewable chemicals. ChemSusChem 2011, 4:451-458.
13. Zakrzewska M.E., Bogel-Lukasik E., Bogel-Lukasik R. Ionic liquid-mediated formation of 5-hydroxymethylfurfurals: a promising biomass-derived building block. Chem. Rev. 2011, 111:397-417.
14. Román-Leshkov Y., Barrett C.J., Liu Z.Y., Dumesic J.A. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 2007, 447:982-986.
15. Lew C.M., Rajabbeigi N., Tsapatsis M. One-pot synthesis of 5-(ethoxymethyl)furfural from glucose using Sn-BEA and Amberlyst catalysts. Ind. Eng. Chem. Res. 2012, 51:5364-5366.
16. Peng L.C., Lin L., Zhang J.H., Shi J.B., Yang Q.L. Conversion of carbohydrates biomass into levulinate esters using heterogeneous catalysts. Appl. Energy 2011, 88:4590-4596.
17. Huber G.W., Chheda J.N., Barrett C.J., Dumesic J.A. Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 2005, 308:1446-1450.
18. Szabolcs A., Molnár M., Dibó G., Mika L.T. Microwave-assisted conversion of carbohydrates to levulinic acid: an essential step in biomass conversion. Green Chem. 2013, 15:439-445.
19. Nakagawa Y., Tomishige K. Total hydrogenation of furan derivatives over silica-supported Ni-Pd alloy catalyst. Catal. Commun. 2010, 12:154-156.
20. Nie J.F., Xie J.H., Liu H.C. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported Ru catalysts. J. Catal. 2013, 301:83-91.
21. Saha B., Gupta D., Abu-Omar M.M., Modak A., Bhaumik A. Porphyrin-based porous organic polymer-supported iron (III) catalyst for efficient aerobic oxidation of 5-hydroxymethyl-furfural into 2,5-furandicarboxylic acid. J. Catal. 2013, 299:316-320.
22. Jadhav A.H., Kim H., Hwang I.T. An efficient and heterogeneous recyclable silicotungstic acid with modified acid sites as a catalyst for conversion of fructose and sucrose into 5-hydroxymethylfurfural in superheated water. Bioresour. Technol. 2013, 132:342-350.
23. Vigier K.D.O., Benguerba A., Barrault J., JérÔme F. Conversion of fructose and inulin to 5-hydroxymethylfurfural in sustainable betaine hydrochloride-based media. Green Chem. 2012, 14:285-289.
24. Nikbin N., Caratzoulas S., Vlachos D.G. A first principles-based microkinetic model for the conversion of fructose to 5-hydroxymethylfurfural. ChemCatChem 2012, 4:504-511.
25. Sidhpuria K.B., Daniel-da-Silva A.L., Trindade T., Coutinho J.A.P. Supported ionic liquid silica nanoparticles (SILnPs) as an efficient and recyclable heterogeneous catalyst for the dehydration of fructose to 5-hydroxymethylfurfural. Green Chem. 2011, 13:340-349.
26. Lai L.K., Zhang Y.G. The effect of imidazolium ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural, and a room temperature catalytic system. ChemSusChem 2011, 3:1257-1259.
27. Okano T., Qiao K., Bao Q.X., Tomida D., Hagiwara H., Yokoyama C. Dehydration of fructose to 5-hydroxymethylfurfural (HMF) in an aqueous acetonitrile biphasic system in the presence of acidic ionic liquids. Appl. Catal. A: Gen. 2013, 451:1-5.
28. Lee Y.Y., Wu K.C.W. Conversion and kinetics study of fructose-to-5-hydroxymethylfurfural (HMF) using sulfonic and ionic liquid groups bi-functionalized mesoporous silica nanoparticles as recyclable solid catalysts in DMSO systems. Phys. Chem. Chem. Phys. 2012, 14:13914-13917.
29. Yan H.P., Yang Y., Tong D.M., Xiang X., Hu C.W. Catalytic conversion of glucose to 5-hydroxymethylfurfural over SO42-/ZrO2 and SO42-/ZrO2-Al2O3 solid acid catalysts. Catal. Commun. 2009, 10:1558-1563.
30. Saravanamurugan S., Paniagua M., Melero J.A., Riisager A. Efficient isomerization of glucose to fructose over zeolites in consecutive reactions in alcohol and aqueous media. J. Am. Chem. Soc. 2013, 135:5246-5249.
31. Chheda J.N., Román-Leshkov Y., Dumesic J.A. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides. Green Chem. 2007, 9:342-350.
32. Tong X.L., Ma Y., Li Y.D. An efficient catalytic dehydration of fructose and sucrose to 5-hydroxymethylfurfural with protic ionic liquids. Carbohydr. Res. 2010, 345:1698-1701.
33. 2 nanoparticles. Appl. Catal. A: Gen. 2011, 409-410:133-139.
34. Li C.Z., Zhang Z.H., Zhao Z.B. Direct conversion of glucose and cellulose to 5-hydroxymethylfurfural in ionic liquid under microwave irradiation. Tetrahedron Lett. 2009, 50:5403-5405.
35. 4 in an ionic liquid. Green Chem. 2009, 11:1746-1749.
36. Lima S., Neves P., Antunes M.M., Pillinger M., Ignatyev N., Valente A.A. Conversion of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic liquids. Appl. Catal. A: Gen. 2009, 363:93-99.
37. Zhang Z.H., Wang Q., Xie H.B., Liu W.J., Zhao Z.B. Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by germanium (IV) chloride in ionic liquids. ChemSusChem 2011, 4:131-138.
38. Liu B., Zhang Z.H., Zhao Z.B. Microwave-assisted catalytic conversion of cellulose into 5-hydroxymethylfurfural in ionic liquids. Chem. Eng. J. 2013, 215-216:517-521.
39. Yang F.L., Liu Q.S., Bai X.F., Du Y.G. Conversion of biomass into 5-hydroxymethylfurfural using solid acid catalyst. Bioresour. Technol. 2011, 102:3424-3429.
40. Zhang J.H., Lin L., Liu S.J. Efficient production of furan derivatives from sugars mixture by catalytic process. Energy Fuels 2012, 26:4560-4567.
41. Takagaki A., Ohara M., Nishimura S., Ebitani K. A one-pot reaction for biorefinery: combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides. Chem. Commun. 2009, 6276-6278.
42. Otomo R., Yokoi T., Kondo J.N., Tatsumi T. Dealuminated beta zeolite as effective bifunctional catalyst for direct transformation of glucose to 5-hydroxymethylfurfural. Appl. Catal. A: Gen. 2014, 470:318-326.
43. Cao Q., Guo X., Yao S., Guan J., Wang X., Mu X., Zhang D. Conversion of hexose into 5-hydroxymethylfurfural in imidazolium ionic liquids with and without a catalyst. Carbohydr. Res. 2011, 346:956-959.
44. Ryu J., Choi J.W., Suh D.J., Ahn D.J., Suh Y.W. Dual catalytic function of 1,3-dialkylimidzolium halide ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural. Catal. Commun. 2012, 24:11-15.
45. Karinen R., Vilonen K., Niemelä M. Biorefining: heterogeneously catalyzed reactions of carbohydrates for the production of furfural and hydroxymethylfurfural. ChemSusChem 2011, 4:1002-1016.
46. Maheria K.C., Kozinski J., Dalai A. Esterification of levulinic acid to butyl levulinate over various acidic zeolites. Catal. Lett. 2013, 143:1220-1225.
47. Patil S.K.R., Lund C.R.F. Formation and growth of humins via aldol addition and condensation during acid-catalyzed conversion of 5-hydroxymethylfurfural. Energy Fuels 2011, 25:4745-4755.
48. Patil S.K.R., Heltzel J., Lund C.R.F. Comparison of structural features of humins formed catalytically from glucose, fructose, and 5-hydroxymethylfurfuraldehyde. Energy Fuels 2012, 26:5281-5293.
49. Wang J.J., Xu W.J., Ren J.W., Liu X.H., Lu G.Z., Wang Y.Q. Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid. Green Chem. 2011, 13:2678-2681.
50. Cai H.L., Li C.Z., Wang A.Q., Xu G.L., Zhang T. Zeolite-promoted hydrolysis of cellulose in ionic liquid, insight into the mutual behavior of zeolite, cellulose and ionic liquid. Appl. Catal. B: Environ. 2012, 123-124:333-338.
51. Hu L., Sun Y., Lin L., Liu S. Catalytic conversion of glucose into 5-hydroxymethylfurfural using double catalysts in ionic liquid. J. Taiwan Inst. Chem. Eng. 2012, 43:718-723.
52. Qi X.H., Watanabe M., Aida T.M., Smith R.L. Fast transformation of glucose and di-/polysaccharides into 5-hydroxymethylfurfural by microwave heating in an ionic liquid/catalyst system. ChemSusChem 2010, 3:1071-1077.
53. Rasrendra C.B., Soetedjo J.N.M., Makertihartha I.G.B.N., Adisasmito S., Heeres H.J. The catalytic conversion of D-glucose to 5-hydroxymethylfurfural in DMSO using metal salts. Top. Catal. 2012, 55:543-549.
54. Zhao Q., Wang L., Zhao S., Wang X.H., Wang S.T. High selective production of 5-hydroymethylfurfural from fructose by a solid heteropolyacid catalyst. Fuel 2011, 90:2289-2293.
55. 2. Tetrahedron Lett. 2012, 53:983-985.
56. Yang Y., Xiang X., Tong D., Hu C.W., Abu-Omar M.M. One-pot synthesis of 5-hydroxymethylfurfural directly from starch over SO42-/ZrO2-Al2O3 solid catalyst. Bioresour. Technol. 2012, 116:302-306.
57. Zhang Y.M., Pidko E.A., Hensen E.J.M. Molecular aspects of glucose dehydration by chromium chlorides in ionic liquids. Chem. Eur. J. 2011, 17:5281-5288.
58. Jansen J.C., Creyghton E.J., Njo S.L., Koningsveld H., Bekkum H. On the remarkable behaviour of zeolite Beta in acid catalysis. Catal. Today 1997, 38:205-212.
59. Beers A. Optimization of zeolite beta by steaming and acid leaching for the acylation of anisole with octanoic acid: a structure-activity relation. J. Catal. 2003, 218:239-248.
60. Poppl A., Rudolf T., Michel D. A pulsed electron nuclear double resonance study of the Lewis acid site-nitric oxide complex in zeolite H-ZSM-5. J. Am. Chem. Soc. 1998, 120:4879-4880.
61. Guan J., Li X.J., Yang G., Zhang W.P., Liu X.C., Han X.W., Bao X.H. Interactions of phosphorous molecules with the acid sites of H-Beta zeolite: insights from solid-state NMR techniques and theoretical calculations. J. Mol. Catal. A: Chem. 2009, 310:113-120.
62. Yang G.H., Zhang X.F., Liu S.Q., Yeung K.L., Wang J.Q. A novel method for the assembly of nano-zeolite crystals on porous stainless steel microchannel and then zeolite film growth. J. Phys. Chem. Solids 2007, 68:26-31.
63. 4 at ZIF-8 magnetic core-shell microspheres and their potential application in a capillary microreactor. Chem. Eng. J. 2013, 228:398-404.
64. Treacy M.M.J., Newsam J.M. Two new three-dimensional twelve-ring zeolite frameworks of which zeolite beta is a disordered intergrowth. Nature 1988, 332:249-251.
65. Kruger J.S., Choudhary V., Nikolakis V., Vlachos D.G. Elucidating the roles of zeolite H-BEA in aqueous-phase fructose sehydration and HMF rehydration. ACS Catal. 2013, 3:1279-1291.
66. Peng L.C., Lin L., Zhang J.H., Shi J.B., Liu S.J. Solid acid catalyzed glucose conversion to ethyl levulinate. Appl. Catal. A: Gen. 2011, 397:259-265.