Optimization of glucose conversion to 5-hydroxymethylfulfural using [BMIM]Cl with ytterbium triflate

Industrial Crops and Products

Volumn 41, Issue 1, 2013, Pages 64-70

  Utami, Syelvia Putri ^a   Amin, NorAishah Saidina ^a  

^a UNIVERSITI TEKNOLOGI MALAYSIA   (Malaysia)

Author keywords

1 Butyl 3 methylimidazolium chloride; 5 Hydroxymethylfulfural; Glucose; Optimization; Response surface methodology; Ytterbium triflate

Indexed keywords

1-BUTYL-3-METHYLIMIDAZOLIUM CHLORIDE; 5-HYDROXYMETHYLFULFURAL; BIODEGRADABLE WASTES; BIOMASS MATERIALS; CATALYST LOADINGS; CENTRAL COMPOSITE DESIGNS; DEHYDRATION PROCESS; EFFECT OF TEMPERATURE; FINE CHEMICALS; GLUCOSE CONVERSION; INTERACTION EFFECT; INVESTIGATE EFFECTS; MODEL COMPOUND; OPTIMUM CONDITIONS; OPTIMUM YIELD; PROCESS PARAMETERS; REACTION TEMPERATURE; RENEWABLE RESOURCE; RESPONSE SURFACE METHODOLOGY; YTTERBIUM TRIFLATE;

AGRICULTURAL WASTES; CATALYSTS; CHLORINE COMPOUNDS; DEHYDRATION; LOADING; OPTIMIZATION; SURFACE PROPERTIES;

GLUCOSE;

BIODEGRADATION; BIOMASS POWER; CATALYST; DEHYDRATION; EXPERIMENTAL STUDY; GLUCOSE; OPTIMIZATION; ORGANIC COMPOUND; RENEWABLE RESOURCE; SOLVENT; TRANSFORMATION; YTTRIUM;

EID: 84860270808     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2012.03.036     Document Type: Article

References (34)

1. 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.
2. 3] as a novel catalyst for the allylation of aldehydes. Tetrahedron Lett. 1994, 35:4639-4640.
3. Aspinall H.C., Greeves N., McIver E.G. Ytterbium triflate catalysed allylation of aldehydes: an unusual benzoic acid induced acceleration. Tetrahedron Lett. 1998, 39:9283-9286.
4. Cao Q., Guo X., Yao S., Guan J., Wang X., Mu X. Conversion of hexose into 5-hydroxymethylfulfural in imidazolium ionic liquids with and without a catalyst. Carbohydr. Res. 2011, 346:956-959.
5. Chambon F., Rataboul F., Pinel C., Cabiac A., Guillon E., Essayem N. Cellulose hydrothermal conversion promoted by heterogeneous Brønsted and Lewis acids: remarkable efficiency of solid Lewis acids to produce lactic acid. Appl. Catal. B 2011, 105:171-181.
6. Guan J., Cao Q., Guo X., Mu X. The mechanism of glucose conversion to 5-hydroxymethylfulfural catalyzed by metal chlorides in ionic liquid: a theoretical study. Comput. Theor. Chem. 2011, 963:453-462.
7. Hameed B.H., Tan I.A.W., Ahmad A.L. Preparation of oil palm empty fruit bunch based activated carbon for removal of 2,4,6-trichlorophenol: optimization using response surface methodology. J. Hazard. Mater. 2009, 164:1316-1324.
8. Hansen T.S., Woodley J.M., Riisager A. Efficient microwave-assisted synthesis of 5-hydroxymethylfulfural from concentrated aqueous fructose. Carbohydr. Res. 2009, 344:2568-2572.
9. Hu L., Sun Y., Lin L. Efficient conversion of glucose into 5-hydroxymethylfurfural by chromium(III) chloride in inexpensive ionic liquid. Ind. Eng. Chem. Res. 2011, 51:1099-1104.
10. Lecomte J., Finiels A., Moreau C. A new selective route to 5-hydroxymethylfurfural from furfural and furfural derivatives over microporous solid acidic catalysts. Ind. Crops Prod. 1999, 9:235-241.
11. Lee J.-W., Ha M.-G., Yi Y.-B., Chung C.-H. Chromium halides mediated production of 5-hydroxymethylfulfural from starch-rich acorn biomass in an acidic ionic liquid. Carbohydr. Res. 2011, 346:177-182.
12. Li C., Zhang Z., Zhao Z.K. Direct conversion of glucose and cellulose to 5-hydroxymethylfulfural in ionic liquid under microwave irradiation. Tetrahedron Lett. 2009, 50:5403-5405.
13. Musau R.M., Munavu R.M. The preparation of 5-hydroxymethyl-2-furaldehyde (5-HMF) from d-fructose in the presence of DMSO. Biomass 1987, 13:67-74.
14. Qi X., Watanabe M., Aida T.M., Smith R.L. Catalytical conversion of fructose and glucose into 5-5-hydroxymethylfulfural in hot compressed water by microwave heating. Catal. Commun. 2008, 9:2244-2249.
15. Qi X., Watanabe M., Aida T.M., Smith R.L. Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids. Green Chem. 2009, 11:1273-1484.
16. Seri K.I., Sakaki T., Shibata M., Inoue Y., Ishida H. Lanthanum(III)-catalyzed degradation of cellulose at 250°C. Bioresour. Technol. 2002, 81:257-260.
17. Shimizu K.-I., Uozumi R., Satsuma A. Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods. Catal Commun. 2009, 10:1849-1853.
18. Sievers C., Valenzuela-Olarte M.B., Marzialetti T., Musin I., Agrawal P.K., Jones C.W. Ionic-liquid-phase hydrolysis of pine wood. Ind. Eng. Chem. Res. 2009, 48:1277-1286.
19. Stahlberg T., Rodriguez-Rodriguez S., Fristrup P., Riisager A. Metal-free dehydration of glucose to 5-(hydroxymethyl)furfural in ionic liquids with boric acid as a promoter. Chem. Eur. J. 2011, 17:1456-1464.
20. Stahlberg T., Sorensen M.G., Riisager A. Direct conversion of glucose to 5-(hydroxymethyl)furfural in ionic liquids with lanthanide catalysts. Green Chem. 2010, 12:321-325.
21. Su Y., Brown H.M., Huang X., Zhou X.-D., Amonette J.E., Zhang Z.C. Single-step conversion of cellulose to 5-5-hydroxymethylfulfural (5-HMF), a versatile platform chemical. Appl. Catal., A 2009, 361:117-122.
22. Su Y., Brown H.M., Li G., Zhou X.D., Amonette J.E., Fulton J.L. Accelerated cellulose depolymerization catalyzed by paired metal chlorides in ionic liquid solvent. Appl. Catal., A 2011, 391:436-442.
23. Swatloski R.P., Spear S.K., Holbrey J.D., Rogers R.D. Dissolution of cellose with ionic liquids. J. Am. Chem. Soc. 2002, 124:4974-4975.
24. Tao F., Song H., Chou L. Catalytic conversion of cellulose to chemicals in ionic liquid. Carbohydr Res. 2011, 346:58-63.
25. Tymchyshyn M., Xu C. Liquefaction of bio-mass in hot-compressed water for the production of phenolic compounds. Bioresour. Technol. 2010, 101:2483-2490.
26. Wang L.-M., Wang Y.-H., Tian H., Yao Y.-F., Shao J.-H., Liu B. Ytterbium triflate as an efficient catalyst for one-pot synthesis of substituted imidazoles through three-component condensation of benzil, aldehydes and ammonium acetate. J. Fluorine Chem. 2006, 127:1570-1573.
27. Wang F., Shi A.-W., Qin X.-X., Liu C.-L., Dong W.-S. Dehydration of fructose to 5-5-hydroxymethylfulfural by rare earth metal trifluoromethanesulfonates in organic solvents. Carbohydr. Res. 2011, 346:982-985.
28. Watanabe M., Aizawa Y., Iida T., Aida T.M., Levy C., Sue K. Glucose reactions with acid and base catalysts in hot compressed water at 473K. Carbohydr. Res. 2005, 340:1925-1930.
29. Wei Z., Li Y., Thushara D., Liu Y., Ren Q. Novel dehydration of carbohydrates to 5-5-hydroxymethylfulfural catalyzed by Ir and Au chlorides in ionic liquids. J. Taiwan Inst. Chem. Eng. 2011, 42:363-370.
30. Werpy T., Petersen G., Aden A., Bozell J., Holladay J., White J. Top Value Added Chemicals from Biomass. Volume 1 - Results of Screening for Potential Candidates from Sugars and Synthesis Gas 2004, U.S. Department Of Energy (DOE), Golden, CO, DOE/GO-102004-1992 (available at www.osti.gov/bridge).
31. Yang F., Liu Q., Bai X., Du Y. Conversion of biomass into 5-hydroxymethylfurfural using solid acid catalyst. Bioresour. Technol. 2011, 102:3424-3429.
32. Zhang Z., Wang Q., Xie H., Liu W., Zhao Z. Catalytic conversion of carbohydrates into 5-5-hydroxymethylfulfural by germanium (IV) chloride in ionic liquids. ChemSusChem 2011, 4:131-138.
33. Zhang Z., Zhao Z. Production of 5-hydroxymethylfurfural from glucose catalyzed by hydroxyapatite supported chromium chloride. Bioresour. Technol. 2011, 102:3970-3972.
34. Zhao H., Holladay J.E., Brown H., Zhang Z.C. Metal chlorides in ionic liquid solvents convert sugars to 5-5-hydroxymethylfulfural. Science 2007, 316:1597-1600.