Reaction pathways of glucose during esterification: Effects of reaction parameters on the formation of humin type polymers

Bioresource Technology

Volumn 102, Issue 21, 2011, Pages 10104-10113

  Hu, Xun ^a   Lievens, Caroline ^a   Larcher, Alfons ^a   Li, Chun Zhu ^a  

^a CURTIN UNIVERSITY   (Australia)

Author keywords

Glucose; Methanolysis; Methyl levulinate; Molecular modification; Polymer suppression

Indexed keywords

ACID CATALYST; AMBERLYST; CARBONYL GROUPS; HIGH TEMPERATURE; LONG RESIDENCE TIME; LOW TEMPERATURES; MASS RATIO; METHANOL/WATER MIXTURES; METHANOLYSIS; METHYL LEVULINATE; MOLECULAR MODIFICATION; POLYMER FORMATION; REACTION PARAMETERS; REACTION PATHWAYS; RESIDENCE TIME; WATER-RICH MEDIUM;

ALDEHYDES; CATALYST ACTIVITY; FURFURAL; GLUCOSE; METHANOL; POLYMERIZATION;

POLYMERS;

5 HYDROXYMETHYLFURFURAL; FURFURAL; GLUCOSE; LEVULINIC ACID; METHANOL; POLYMER; WATER;

CARBONYL COMPOUND; CATALYST; ESTER; GLUCOSE; HIGH TEMPERATURE; METHANOL; MOLECULAR ANALYSIS; PARAMETERIZATION; POLYMER; POLYMERIZATION; REACTION KINETICS; WATER MASS;

ACETALIZATION; ARTICLE; CHEMICAL PHENOMENA; ESTERIFICATION; ETHERIFICATION; HIGH TEMPERATURE; LOW TEMPERATURE; METHANOLYSIS; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; RESIDENCE TIME;

CATALYSIS; ELEMENTS; ESTERIFICATION; FURALDEHYDE; GLUCOSE; HUMIC SUBSTANCES; HYDROQUINONES; KINETICS; METHANOL; MODELS, CHEMICAL; POLYMERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE; TIME FACTORS; WATER;

EID: 80053119491     PISSN: 09608524     EISSN: 18732976     Source Type: Journal    
DOI: 10.1016/j.biortech.2011.08.040     Document Type: Article

References (31)

1. Asghari F.S., Yoshida H. Acid-catalyzed production of 5-hydroxymethyl furfural from D-fructose in subcritical water. Ind. Eng. Chem. Res. 2006, 45:2163-2173.
2. Chen C.C., Mcginnis G.D. The use of 1-methylimidazole as a solvent and catalyst for the preparation of aldononitrile acetates of aldoses. Carbohydr. Res. 1981, 90:127-130.
3. Chuntanapum A., Matsumura Y. Formation of tarry material from 5-HMF in subcritical and supercritical water. Ind. Eng. Chem. Res. 2009, 48:9837-9846.
4. Chuntanapum A., Matsumura Y. Char formation mechanism in supercritical water gasification process: a study of model compounds. Ind. Eng. Chem. Res. 2010, 49:4055-4062.
5. Corma A., Iborra S., Velty A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 2007, 107:2411-2502.
6. Dias A.S., Lima S., Carriazo D., Rives V., Pillinger M., Valente A.A. Exfoliated titanate, niobate and titanoniobate nanosheets as solid acid catalysts for the liquid-phase dehydration of D-xylose into furfural. J. Catal. 2006, 244:230-237.
7. Deng W., Liu M., Zhang Q., Tan X., Wang Y. Acid-catalysed direct transformation of cellulose into methyl glucosides in methanol at moderate temperatures. Chem. Commun. 2010, 46:2668-2670.
8. Dobele G., Rossinskaja G., Dizhbite T., Telysheva G., Meier D., Faix O. Application of catalysts for obtaining 1,6-anhydrosaccharides from cellulose and wood by fast pyrolysis. J. Anal. Appl. Pyrolysis 2005, 74:401-405.
9. Heeres H., Handana R., Chunai D., Rasrendra C.B., Girisuta B., Heeres H.J. Combined dehydration/(transfer)-hydrogenation of C6-sugars (d-glucose and d-fructose) to γ-valerolactone using ruthenium catalysts. Green Chem. 2009, 11:1247-1255.
10. Hilten R.N., Bibens B.P., Kastner J.R., Das K.C. In-line esterification of pyrolysis vapor with ethanol improves bio-oil quality. Energy Fuels 2010, 24:673-682.
11. Huber G.W., Iborra S., Corma A. Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem. Rev. 2006, 106:4044-4098.
12. Islam M.R., Parveen M., Haniu H. Properties of sugarcane waste-derived bio-oils obtained by fixed-bed fire-tube heating pyrolysis. Bioresour. Technol. 2010, 101:4162-4168.
13. Li N., Tompsett G.A., Zhang T., Shi J., Wyman C.E., Huber G.W. Renewable gasoline from aqueous phase hydrodeoxygenation of aqueous sugar solutions prepared by hydrolysis of maple wood. Green Chem. 2011, 13:91-101.
14. Lohitharn N., Shanks B.H. Upgrading of bio-oil: effect of light aldehydes on acetic acid removal via esterification. Catal. Commun. 2009, 11:96-99.
15. Luijkx G.C.A., Rantwijk F., Bekkum H. Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and-fructose. Carbohydr. Res. 1993, 242:131-139.
16. Marquevich M., Czernik S., Chornet E., Montane D. Hydrogen from biomass: steam reforming of model compounds of fast-pyrolysis oil. Energy Fuels 1999, 13:1160-1166.
17. Matsumura Y., Sasaki M., Okuda K., Takami S., Ohara S., Umetsu M., Adschiri T. Supercritical water treatment of biomass for energy and material recovery. Combust. Sci. Technol. 2006, 178:509-536.
18. Megawati, Sediawan W.B., Sulistyo H., Hidayat M. Kinetics of sequential reaction of hydrolysis and sugar degradation of rice husk in ethanol production: effect of catalyst concentration. Bioresour. Technol. 2011, 102:2062-2067.
19. Moens L., Black S.K., Myers M.D., Czernik S. Study of the neutralization and stabilization of a mixed hardwood bio-oil. Energy Fuels 2009, 23:2695-2699.
20. Palkovits R. Pentenoic acid pathways for cellulosic biofuels. Angew. Chem. Int. Ed. 2010, 49:4336-4338.
21. Peng J., Chen P., Lou H., Zheng X. Catalytic upgrading of bio-oil by HZSM-5 in sub-and super-critical ethanol. Bioresour. Technol. 2009, 100:3415-3418.
22. 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.
23. Rasrendra C.B., Makertihartha I.G.B.N., Adisasmito S., Heeres H.J. Green chemicals from d-glucose: systematic studies on catalytic effects of inorganic salts on the chemo-selectivity and yield in aqueous solutions. Top. Catal. 2010, 53:1241-1247.
24. Sharma K., Bakhshi N. Upgrading of wood derived bio-oil over HZSM-5. Bioresour. Technol. 1991, 35:57-66.
25. Shaw P.E., Tatum J.H., Berry R.E. 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, a degradation product of a hexose. Carbohydr. Res. 1971, 16:207-211.
26. Takeuchi Y., Jin F., Tohji K., Enomoto H. Acid catalytic hydrothermal conversion of carbohydrate biomass into useful substances. J. Mater. Sci. 2008, 43:2472-2475.
27. Tang Z., Lu Q., Zhang Y., Zhu X., Guo Q. One step bio-oil upgrading through hydrotreatment, esterification, and cracking. Ind. Eng. Chem. Res. 2009, 48:6923-6929.
28. Tominaga K., Mori A., Fukushima Y., Shimada S., Sato K. Mixed-acid systems for the catalytic synthesis of methyl levulinate from cellulose. Green Chem. 2011, 13:810-812.
29. Wildschut J., Arentz J., Rasrendra C.B., Venderbosch R.H., Heeres H.J. Catalytic hydrotreatment of fast pyrolysis oil: model studies on reaction pathways for the carbohydrate fraction. Environ. Prog. Sustain. Energy 2009, 28:450-460.
30. Yu Y., Lou X., Wu H. Some recent advances in hydrolysis of biomass in hot-compressed water and its comparisons with other hydrolysis methods. Energy Fuels 2008, 22:46-60.
31. Zhang Q., Chang J., Wang T., Xu Y. Upgrading bio-oil over different solid catalysts. Energy Fuels 2006, 20:2717-2720.