Production enhancement of 5-hydroxymethyl furfural from fructose via mechanical stirring control and high-fructose solution addition

Journal of Chemical Technology and Biotechnology

Volumn 89, Issue 1, 2014, Pages 56-64

  Jiang, Nan ^a   Qi, Wei ^a   Huang, Renliang ^a   Wang, Mengfan ^a   Su, Rongxin ^a   He, Zhimin ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

5 hydroxymethylfurfural; Biphasic system; Fructose; High fructose solution addition; Stirring speed

Indexed keywords

OPTIMIZATION; RATE CONSTANTS; REACTION KINETICS;

5 HYDROXYMETHYL FURFURALS; BIPHASIC SYSTEMS; EFFICIENT PROCESS; HIGH-FRUCTOSE SOLUTION ADDITION; HIGH-VALUE CHEMICALS; MECHANICAL STIRRING; PRODUCTION ENHANCEMENT; STIRRING SPEED;

FRUCTOSE;

5 HYDROXYMETHYLFURFURAL; BUTANOL; FRUCTOSE; LEVULINIC ACID; WATER;

ADDITION REACTION; ARTICLE; CATALYST; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; MOLECULAR DYNAMICS; POLYMERIZATION; REACTION TIME; VELOCITY;

EID: 84897041295     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.4096     Document Type: Article

References (35)

1. Roman-Leshkov Y, Chheda JN and Dumesic JA, Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312:1933-1937 (2006).
2. Roman-Leshkov Y, Barrett CJ, Liu ZY and Dumesic JA, Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447:982-985 (2007).
3. Holm MS, Pagan-Torres YJ, Saravanamurugan S, Riisager A, Dumesic JA and Taarning E, Sn-Beta catalysed conversion of hemicellulosic sugars. Green Chem 14:702-706 (2012).
4. Tong X, Ma Y and Li Y, Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes. Appl Catal A: Gen 385:1-13 (2010).
5. Chheda JN, Huber GW and Dumesic JA, Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angew Chem Int Edit 46:7164-7183 (2007).
6. Hew KL, Tamidi AM, Yusup S, Lee KT and Ahmad MM, Catalytic cracking of bio-oil to organic liquid product (OLP). Bioresource Technol 101:8855-8858 (2010).
7. Rosatella AA, Simeonov SP, Frade RFM and Afonso CAM, 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754-793 (2011).
8. Huang R, Qi W, Su R and He Z, Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural. Chem Commun (Cambridge) 46:1115-1117 (2009).
9. Qi XH, Guo HX and Li LY, Efficient conversion of fructose to 5-hydroxymethylfurfural catalyzed by sulfated zirconia in ionic liquids. Ind Eng Chem Res 50:7985-7989 (2011).
10. Long J, Guo B, Teng J, Yu Y, Wang L and Li X, SO3H-functionalized ionic liquid: efficient catalyst for bagasse liquefaction. Bioresource Technol 102:10114-10123 (2011).
11. Su Y, Brown HM, Li G, Zhou X-d, Amonette JE, Fulton JL, Camaioni DM and Zhang ZC, Accelerated cellulose depolymerization catalyzed by paired metal chlorides in ionic liquid solvent. Appl Catal A: Gen 391:436-442 (2011).
12. Qi XH, Watanabe M, Aida TM and Smith RL, Catalytic conversion of cellulose into 5-hydroxymethylfurfural in high yields via a two-step process. Cellulose 18:1327-1333 (2011).
13. Qi XH, Watanabe M, Aida TM and Smith RL, Efficient catalytic conversion of fructose into 5-hydroxymethylfurfural in ionic liquids at room temperature. Chemsuschem 2:944-946 (2009).
14. Hsu W-H, Lee Y-Y, Peng W-H and Wu KCW, Cellulosic conversion in ionic liquids (ILs): effects of H2O/cellulose molar ratios, temperatures, times, and different ILs on the production of monosaccharides and 5-hydroxymethylfurfural (HMF). Catal Today 174:65-69 (2011).
15. Wang P, Yu H, Zhan S and Wang S, Catalytic hydrolysis of lignocellulosic biomass into 5-hydroxymethylfurfural in ionic liquid. Bioresource Technol 102:4179-4183 (2011).
16. Qi XH, Watanabe M, Aida TM and Smith RL, fast transformation of glucose and Di-/polysaccharides into 5-hydroxymethylfurfural by microwave heating in an ionic liquid/catalyst system. Chemsuschem 3:1071-1077 (2010).
17. Yu S, Brown HM, Huang XW, Zhou XD, Amonette JE and Zhang ZC, Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical. Appl Catal A Gen 361:117-122 (2009).
18. Peng W-H, Lee Y-Y, Wu C and Wu KCW, Acid-base bi-functionalized, large-pored mesoporous silica nanoparticles for cooperative catalysis of one-pot cellulose-to-HMF conversion. J Mater Chem 22:23181 (2012).
19. Lee Y-Y and Wu KCW, 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 14:13914-13917 (2012).
20. Ribeiro Gallo JM, Martin Alonso D, Mellmer M and Dumesic J, Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents. Green Chem 15:85-90 (2012).
21. Moreau C, Finiels A and Vanoye L, Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst. J Molec Catal A: Chem 253:165-169 (2006).
22. Thananatthanachon T and Rauchfuss TB, Efficient production of the liquid fuel 2, 5-dimethylfuran from fructose using formic acid as a reagent. Angewandte Chemie Int Ed 49:6616-6618 (2010).
23. Carniti P, Gervasini A and Marzo M, Absence of expected side-reactions in the dehydration reaction of fructose to HMF in water over niobic acid catalyst. Catal Commun 12:1122-1126 (2011).
24. Amiri H, Karimi K and Roodpeyma S, Production of furans from rice straw by single-phase and biphasic systems. Carbohyd Res 345:2133-2138 (2010).
25. Asghari FS and Yoshida H, Acid-catalyzed production of 5-hydroxymethyl furfural from D-fructose in subcritical water. Ind Eng Chem Res 45:2163-2173 (2006).
26. Li Y, Lu X, Yuan L and Liu X, Fructose decomposition kinetics in organic acids-enriched high temperature liquid water. Biomass Bioenergy 33:1182-1187 (2009).
27. Zhao QA, Wang L, Zhao S, Wang XH and Wang ST, High selective production of 5-hydroymethylfurfural from fructose by a solid heteropolyacid catalyst. Fuel 90:2289-2293 (2011).
28. Lee Y-S, Yeh M-Y and Shih Y-P, Phase-transfer catalytic kinetics of the synthesis of phenyl benzoate. Ind Eng Chem Res 34:1572-1580 (1995).
29. Kaczmarczyk E, Janus E, Milchert E and Karakulski K, Kinetic study of the phase-transfer catalytic epoxidation of 1, 4-bis(allyloxy)butane. J Colloid Interface Sci 365:191-197 (2012).
30. Zhang MJ, Wang F, Su RX, Qi W and He ZM, Ethanol production from high dry matter corncob using fed-batch simultaneous saccharification and fermentation after combined pretreatment. Bioresource Technol 101:4959-4964 (2010).
31. Nikolla E, Roman-Leshkov Y, Moliner M and Davis ME, "One-pot" synthesis of 5-(hydroxymethyl)furfural from carbohydrates using tin-beta zeolite. ACS Catal 1:408-410 (2011).
32. Hansen TS, Woodley JM and Riisager A, Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose. Carbohyd Res 344:2568-2572 (2009).
33. Kuster BFM, 5-Hydroxymethylfurfural (HMF). A review focussing on its manufacture. Starch - Stärke 42:314-321 (1990).
34. Mushrif SH, Caratzoulas S and Vlachos DG, Understanding solvent effects in the selective conversion of fructose to 5-hydroxymethyl-furfural: a molecular dynamics investigation. Phys Chem Chem Phys 14:2637-2644 (2012).
35. Fan C, Guan H, Zhang H, Wang J, Wang S and Wang X, Conversion of fructose and glucose into 5-hydroxymethylfurfural catalyzed by a solid heteropolyacid salt. Biomass Bioenergy 35:2659-2665 (2011).