Magnetic lignin-derived carbonaceous catalyst for the dehydration of fructose into 5-hydroxymethylfurfural in dimethylsulfoxide

Chemical Engineering Journal

Volumn 263, Issue , 2015, Pages 299-308

  Hu, Lei ^a   Tang, Xing ^b   Wu, Zhen ^a   Lin, Lu ^b   Xu, Jiaxing ^a   Xu, Ning ^a   Dai, Benlin ^a  

^a HUAIYIN NORMAL UNIVERSITY   (China)

^b XIAMEN UNIVERSITY   (China)

Author keywords

5 Hydroxymethylfurfural; Dehydration; Dimethylsulfoxide; Fructose; Magnetic lignin derived carbonaceous catalyst

Indexed keywords

CARBONIZATION; DEHYDRATION; DIMETHYL SULFOXIDE; ENZYMATIC HYDROLYSIS; FRUCTOSE; LIGNIN; MAGNETISM;

5 HYDROXYMETHYL FURFURALS; CARBONACEOUS CATALYST; CATALYTIC STABILITY; ENZYMATIC HYDROLYSIS LIGNINS; HIGH SURFACE AREA; POROUS STRUCTURES; REACTION CONDITIONS; SULFONATION PROCESS;

CATALYST ACTIVITY;

EID: 84912144824     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.11.044     Document Type: Article

References (58)

1. Chinnappan A., Jadhav A.H., Kim H. Ionic liquid with metal complexes: an efficient catalyst for selective dehydration of fructose to 5-hydroxymethylfurfural. Chem. Eng. J. 2014, 237:95-100.
2. Wu C.Y., Chen W., Zhong L.X., Peng X.W., Sun R.C., Fang J.J., Zheng S.B. Conversion of xylose into furfural using lignosulfonic acid as catalyst in ionic liquid. J. Agric. Food Chem. 2014, 62:7430-7435.
3. Tsilomelekis G., Josephson T.R., Nikolakis V., Caratzoulas S. Origin of 5-hydroxymethylfurfural stability in water/dimethyl sulfoxide mixtures. ChemSusChem 2014, 7:117-126.
4. 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.
5. Fang Z.F., Liu B., Luo J.J., Ren Y.S., Zhang Z.H. Efficient conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by the chromium-exchanged montmorillonite K-10 clay. Biomass Bioenergy 2014, 60:171-177.
6. Teong S.P., Yi G.S., Zhang Y.G. Hydroxymethylfurfural production from bioresources: past, present and future. Green Chem. 2014, 16:2015-2026.
7. van Putten R.J., van der Waal J.C., de Jong E., Rasrendra C.B., Heeres H.J., de Vries J.G. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem. Rev. 2013, 113:1499-1597.
8. Zakrzewska M.E., Bogel-Łukasik E., Bogel-Łukasik R. Ionic liquid-mediated formation of 5-hydroxymethylfurfurals: a promising biomass-derived building block. Chem. Rev. 2011, 111:397-417.
9. 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.
10. Yang Y.L., Du Z.T., Ma J.P., Lu F., Zhang J.J., Xu J. Biphasic catalytic conversion of fructose by continuous hydrogenation of HMF over a hydrophobic ruthenium catalyst. ChemSusChem 2014, 7:1352-1356.
11. Yao S.X., Wang X.C., Jiang Y.J., Wu F., Chen X.G., Mu X.D. One-step conversion of biomass-derived 5-hydroxymethylfurfural to 1,2,6-hexanetriol over Ni-Co-Al mixed oxide catalysts under mild conditions. ACS Sustainable Chem. Eng. 2013, 2:173-180.
12. Hu L., Tang X., Xu J.X., Wu Z., Lin L., Liu S.J. Selective transformation of 5-hydroxymethylfurfural into the liquid fuel 2,5-dimethylfuran over carbon-supported ruthenium. Ind. Eng. Chem. Res. 2014, 53:3056-3064.
13. 4 nanoparticles supported phosphotungstic acid: a novel environmentally friendly catalyst for the synthesis of 5-ethoxymethylfurfural from 5-hydroxymethylfurfural and fructose. Catal. Sci. Technol. 2013, 3:2104-2112.
14. Zhang J.H., Lin L., Liu S.J. Efficient production of furan derivatives from a sugar mixture by catalytic process. Energy Fuels 2012, 26:4560-4567.
15. 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.
16. Kwon Y., de Jong E., Raoufmoghaddam S., Koper M.T. Electrocatalytic hydrogenation of 5-hydroxymethylfurfural in the absence and presence of glucose. ChemSusChem 2013, 6:1659-1667.
17. Lin Z.J., Ierapetritou M., Nikolakis V. Aromatics from lignocellulosic biomass: economic analysis of the production of p-xylene from 5-hydroxymethylfurfural. AIChE J. 2013, 59:2079-2087.
18. Siankevich S., Savoglidis G., Fei Z.F., Laurenczy G., Alexander D.T.L., Yan N., Dyson P.J. A novel platinum nanocatalyst for the oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under mild conditions. J. Catal. 2014, 315:67-74.
19. Zhang Z.H., Liu B., Lv K.L., Sun J., Deng K.J. Aerobic oxidation of biomass derived 5-hydroxymethylfurfural into 5-hydroxymethyl-2-furancarboxylic acid catalyzed by a montmorillonite K-10 clay immobilized molybdenum acetylacetonate complex. Green Chem. 2014, 16:2762-2770.
20. Zhang Z.H., Yuan Z.L., Tang D.G., Ren Y.S., Lv K.L., Liu B. Iron oxide encapsulated by ruthenium hydroxyapatite as heterogeneous catalyst for the synthesis of 2,5-diformylfuran. ChemSusChem 2014, 10.1002/cssc.201402402.
21. 2 solid acid for conversion of fructose to 5-hydroxymethylfurfural. ChemSusChem 2014, 7:1703-1709.
22. 6-monosaccharides to 5-hydroxymethylfurfural in dimethyl sulfoxide using sulfonic acid heterogeneous catalysts. Chin. J. Catal. 2014, 35:696-707.
23. Arias K.S., Al-Resayes S.I., Climent M.J., Corma A., Iborra S. From biomass to chemicals: synthesis of precursors of biodegradable surfactants from 5-hydroxymethylfurfural. ChemSusChem 2013, 6:123-131.
24. Wang H.L., Kong Q.Q., Wang Y.X., Deng T.S., Chen C.M., Hou X.L., Zhu Y.L. Graphene oxide catalyzed dehydration of fructose into 5-hydroxymethylfurfural with isopropanol as cosolvent. ChemCatChem 2014, 6:728-732.
25. Qi X.H., Guo H.X., Li L.Y. Efficient conversion of fructose to 5-hydroxymethylfurfural catalyzed by sulfated zirconia in ionic liquids. Ind. Eng. Chem. Res. 2011, 50:7985-7989.
26. Liu R.L., Chen J.Z., Huang X., Chen L.M., Ma L.L., Li X.J. Conversion of fructose into 5-hydroxymethylfurfural and alkyl levulinates catalyzed by sulfonic acid-functionalized carbon materials. Green Chem. 2013, 15:2895-2903.
27. Hu L., Zhao G., Tang X., Wu Z., Xu J.X., Lin L., Liu S.J. Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural over cellulose-derived carbonaceous catalyst in ionic liquid. Bioresour. Technol. 2013, 148:501-507.
28. 4 in DMSO and [BMIM]Cl system at room temperature. Carbohydr. Polym. 2012, 88:891-895.
29. Hu L., Sun Y., Lin L. Ionic liquids-mediated formation of 5-hydroxymethylfurfural. Prog. Chem. 2012, 24:483-491.
30. Karimi B., Mirzaei H.M. The influence of hydrophobic/hydrophilic balance of the mesoporous solid acid catalysts in the selective dehydration of fructose into HMF. RSC Adv. 2013, 3:20655-20661.
31. Li Y., Liu H., Song C.H., Gu X.M., Li H.M., Zhu W.S., Yin S., Han C.R. The dehydration of fructose to 5-hydroxymethylfurfural efficiently catalyzed by acidic ion-exchange resin in ionic liquid. Bioresour. Technol. 2013, 133:347-353.
32. Benoit M., Brissonnet Y., Guelou E., De Oliveira Vigier K., Barrault J., Jerome F. Acid-catalyzed dehydration of fructose and inulin with glycerol or glycerol carbonate as renewably sourced co-solvent. ChemSusChem 2010, 3:1304-1309.
33. Jadhav A.H., Chinnappan A., Patil R.H., Kostjuk S.V., Kim H. Green chemical conversion of fructose into 5-hydroxymethylfurfural (HMF) using unsymmetrical dicationic ionic liquids under mild reaction condition. Chem. Eng. J. 2014, 243:92-98.
34. Guo F., Fang Z., Zhou T.J. Conversion of fructose and glucose into 5-hydroxymethylfurfural with lignin-derived carbonaceous catalyst under microwave irradiation in dimethyl sulfoxide-ionic liquid mixtures. Bioresour. Technol. 2012, 112:313-318.
35. Xiao S.H., Liu B., Wang Y.M., Fang Z.F., Zhang Z.H. Efficient conversion of cellulose into biofuel precursor 5-hydroxymethylfurfural in dimethyl sulfoxide-ionic liquid mixtures. Bioresour. Technol. 2014, 151:361-366.
36. Rinaldi R., Schuth F. Acid hydrolysis of cellulose as the entry point into biorefinery schemes. ChemSusChem 2009, 2:1096-1107.
37. Cai C.M., Zhang T.Y., Kumar R., Wyman C.E. THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass. Green Chem. 2013, 15:3140-3145.
38. Asghari F.S., Yoshida H. Acid-catalyzed production of 5-hydroxymethylfurfural from fructose in subcritical water. Ind. Eng. Chem. Res. 2006, 45:2163-2173.
39. 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. Am. Chem. Soc. 2013, 135:3997-4006.
40. Hu L., Wu Z., Xu J.X., Sun Y., Lin L., Liu S.J. Zeolite-promoted transformation of glucose into 5-hydroxymethylfurfural in ionic liquid. Chem. Eng. J. 2014, 244:137-144.
41. 3 solid acid catalysts. Catal. Commun. 2009, 10:1558-1563.
42. Sampath G., Kannan S. Fructose dehydration to 5-hydroxymethylfurfural: remarkable solvent influence on recyclability of Amberlyst-15 catalyst and regeneration studies. Catal. Commun. 2013, 37:41-44.
43. 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.
44. Chen J.Z., Li K.G., Chen L.M., Liu R.L., Huang X., Ye D.Q. Conversion of fructose into 5-hydroxymethylfurfural catalyzed by recyclable sulfonic acid-functionalized metal-organic frameworks. Green Chem. 2014, 16:2490-2499.
45. Dutta A., Gupta D., Patra A.K., Saha B., Bhaumik A. Synthesis of 5-hydroxymethylfurural from carbohydrates using large-pore mesoporous tin phosphate. ChemSusChem 2014, 7:925-933.
46. Wang L., Zhang J., Zhu L.F., Meng X.J., Xiao F.S. Efficient conversion of fructose to 5-hydroxymethylfurfural over sulfated porous carbon catalyst. J. Energy Chem. 2013, 22:241-244.
47. Qi X.H., Guo H.X., Li L.Y., Smith R.L. Acid-catalyzed dehydration of fructose into 5-hydroxymethylfurfural by cellulose-derived amorphous carbon. ChemSusChem 2012, 5:2215-2220.
48. 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.
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. 4 at C nanoparticles as magnetically recyclable solid acid catalysts for acetalization reaction. Dalton Trans. 2014, 43:1220-1227.
51. Liu W.J., Tian K., Jiang H., Yu H.Q. Facile synthesis of highly efficient and recyclable magnetic solid acid from biomass waste. Sci. Rep. 2013, 3:2419-2425.
52. 4 at C nanoparticles with great performance in biomedicine. J. Mater. Chem. B 2014, 2:4481-4488.
53. 3H, COOH, and OH groups. J. Am. Chem. Soc. 2008, 130:12787-12793.
54. Liu Z.G., Zhang F.S. Nano-zerovalent iron contained porous carbons developed from waste biomass for the adsorption and dechlorination of PCBs. Bioresour. Technol. 2010, 101:2562-2564.
55. Suganuma S., Nakajima K., Kitano M., Yamaguchi D., Kato H., Hayashi S., Hara M. Synthesis and acid catalysis of cellulose-derived carbon-based solid acid. Solid State Sci. 2010, 12:1029-1034.
56. Huang Z., Pan W.Y., Zhou H.B., Qin F., Xu H.L., Shen W. Nafion-resin-modified mesocellular silica foam catalyst for 5-hydroxymethylfurfural production from d-fructose. ChemSusChem 2013, 6:1063-1069.
57. 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.
58. De S., Dutta S., Saha B. Microwave assisted conversion of carbohydrates and biopolymers to 5-hydroxymethylfurfural with aluminium chloride catalyst in water. Green Chem. 2011, 13:2859-2868.