Kinetic studies on chromium-catalyzed conversion of glucose into 5-hydroxymethylfurfural in alkylimidazolium chloride ionic liquid

Chemical Engineering Journal

Volumn 237, Issue , 2014, Pages 55-61

  Zhang, Jian ^a,b   Cao, Yan ^b   Li, Huiquan ^b   Ma, Xinbin ^a  

^a TIANJIN UNIVERSITY   (China)

^b INSTITUTE OF PROCESS ENGINEERING   (China)

Author keywords

5 Hydroxymethylfurfural; Glucose; Ionic liquid; Kinetic study

Indexed keywords

5 HYDROXYMETHYL FURFURALS; ALKYLIMIDAZOLIUM; GLUCOSE CONCENTRATION; GLUCOSE CONVERSION; ISOMERIZATION REACTION; KINETIC STUDY; PLATFORM CHEMICALS; REACTION TEMPERATURE;

ACTIVATION ENERGY; CHLORINE COMPOUNDS; CHROMIUM; HYDROGEN BONDS; IONIC LIQUIDS; ISOMERIZATION; KINETIC THEORY; KINETICS; RATE CONSTANTS; REACTION KINETICS;

GLUCOSE;

EID: 84886526187     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2013.10.007     Document Type: Article

References (39)

1. Huber G.W., Iborra S., Corma A. Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem. Rev. 2006, 106:4044-4098.
2. Stöker Michael. Biofuels and biomass-to-liquid fuels in the biorefinery: catalytic conversion of lignocellulosic biomass using porous materials. Angew. Chem. Int. Ed. 2008, 47:9200-9211.
3. Lewkowski J. Synthesis, chemsitry and application of 5-hydroxymethylfurfural and its derivatives. ARKIVOC 2001, 14-17.
4. Gandini A., Coelho D., Gomes M., Reis B., Silvestre A. Materials from renewable resources based on furan monomers and furan chemistry: work in progress. J. Mater. Chem. 2009, 19:8656-8664.
5. Zakrzewska M.E., Bogel-Lukasik E., Bogel-Lukasik R. Ionic liquid-mediated formation of 5-hydroxymethylfurfural-a promising biomass-derived building block. Chem. Rev. 2011, 111:397-417.
6. Geboers J.A., Van de Vyver S., Ooms R., Op de Beeck B., Jacobs P.A., Sels B.F. Chemocatalytic conversion of cellulose: opportunities, advances and pitfalls. Catal. Sci. Technol. 2011, 1:714-726.
7. van Dam H.E., Kieboom A.P.G., van Bekkum H. The conversion of fructose and glucose in acidic media: formation of hydroxymethylfurfural. Starch-Stäke 1986, 38:95-101.
8. 3 solid acid catalysts. Catal. Commun. 2009, 10:1558-1563.
9. Kabyemela B.M., Adschiri T., Malaluan R.M., Arai K. Kinetics of glucose epimerization and decomposition in subcritical and supercritical water. Ind. Eng. Chem. Res. 1997, 36:1552-1558.
10. Tyrlik S.K., Szerszen D., Olejnik M., Danikiewicz W. Selective dehydration of glucose to hydroxymethylfurfural and a one-pot synthesis of a 4-acetylbutyrolactone from glucose and trioxane in solutions of aluminium salts. Carbohydr. Res. 1999, 315:268-272.
11. 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.
12. Chheda J.N., Roman-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.
13. Tong X.L., Ma Y., Li Y.D. Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes. App. Catal. A 2010, 385:1-13.
14. Rosatella A.A., Simeonov S.P., Frade R.F.M., Afonso C.A.M. 5-hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem. 2011, 13:754-793.
15. 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.
16. Yong G., Zhang Y.G., Ying J.Y. Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose. Angew. Chem. Int. Ed. 2008, 47:9345-9348.
17. 4 in an ionic liquid. Green Chem. 2009, 11:1746-1749.
18. Li C., Zhang Z., Zhao Z.K. Direct conversion of glucose and cellulose to 5-hydroxymethylfurfural in ionic liquid under microwave irradiation. Tetrahedron Lett. 2009, 50:5403-5405.
19. Chen T.M., Lin L. Conversion of glucose in CPL-LiCl to 5-hydroxymethylfurfural. Chin. J. Chem. 2010, 28:1773-1776.
20. 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.
21. Ståhlberg T., Sørensen M.G., Riisager A. Direct conversion of glucose to 5-(hydroxymethyl)furfural in ionic liquids with lanthanide catalysts. Green Chem. 2010, 12:321.
22. Binder J.B., Cefali A.V., Blank J.J., Raines R.T. Mechanistic insights on the conversion of sugars into 5-hydroxymethylfurfural. Energy Environ. Sci. 2010, 3:765-771.
23. 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.
24. Román-Leshkov Y., Moliner M., Labinger J.A., Davis M.E. Mechanism of glucose isomerization using a solid lewis acid catalyst in water. Angew. Chem. Int. Ed. 2010, 49:8954-8957.
25. Pescarmona P.P., Janssen K.P.F., Delaet C., Stroobants C., Houthoofd K., Philippaerts A., De Jonghe C., Paul J.S., Jacobs P.A., Sels B.F. Zeolite-catalysed conversion of C3 sugars to alkyl lactates. Green Chem. 2010, 12:1083-1089.
26. 2+dimers. Angew. Chem. Int. Ed. 2010, 49:2530-2534.
27. Zhang Y., Pidko E.A., Hensen E.J.M. Molecular aspects of glucose dehydration by chromium chlorides in ionic liquids. Chem. Eur. J. 2011, 17:5280-5287.
28. Mckibbins S.W., Harris J.F., Saeman J.F. Kinetics of the acid catalyzed conversion of glucose to 5-hydroxymethyl-2-furadehyde and levulinic acid. For. Prod. J. 1962, 17-23.
29. Xiang Q., Lee Y., Torget R. Kinetics of glucose decomposition during dilute-acid hydrolysis of lignocellulosic biomass. Appl. Biochem. Biotechnol. 2004, 115:1127-1138.
30. Girisuta B., Janssen L.P.B.M., Heeres H.J. Green chemicals: a kinetic study on the conversion of glucose to levulinic acid. Chem. Eng. Res. Des. 2006, 84:339-349.
31. Yu Y., Wu H. Kinetics and mechanism of glucose decomposition in hot-compressed water: effect of initial glucose concentration. Ind. Eng. Chem. Res. 2011, 50:10500-10508.
32. 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.
33. Zhang H., Wu J., Zhang J., He J. 1-allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 2005, 38:8272-8277.
34. Antal M.J., Mok W.S.L., Richards G.N. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose. Carbohydr. Res. 1990, 199:91-109.
35. Kabyemela B.M., Adschiri T., Malaluan R.M., Arai K. Glucose and fructose decomposition in subcritical and supercritical water: detailed reaction pathway, mechanisms, and kinetics. Ind. Eng. Chem. Res. 1999, 38:2888-2895.
36. Pilath H.M., Nimlos M.R., Mittal A., Himmel M.E., Johnson D.K. Glucose reversion reaction kinetics. J. Agric. Food Chem. 2010, 58:6131-6140.
37. Sievers C., Musin I., Marzialetti T., Olarte M.B.V., Agrawal P.K., Jones C.W. Acid-catalyzed conversion of sugars and furfurals in an ionic-liquid phase. Chemsuschem 2009, 2:665-671.
38. Kuster B.F.M. 5-hydroxymethylfurfural (HMF). A review focusing on its manufacture. Starch-Stäke 1990, 42:314-321.
39. He X.M., Agnihotri G., Liu H.W. Novel enzymatic mechanisms in carbohydrate metabolism. Chem. Rev. 2000, 100:4615-4661.