• Journal of Korea Technical Association of The Pulp and Paper Industry
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• v.45 no.2
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• pp.21-26
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• 2013

Conversion of fructose to 5-hydroxymethylfurfural (5-HMF) was investigated in dimethylsulfoxide (DMSO) solvent with increasing reaction temperatures and impact of residual water from dehydration reaction byproduct. To convert fructose to 5-HMF, increasing reaction temperature led more conversion to 5-HMF than lower temperature at the range of $120-150^{\circ}C$ in DMSO solvent. DMSO engaged in the acid-catalyzed dehydration and rearrangement reaction as acid and solvent. Increasing temperature led to more furanose structure than pyranose at the range of $30-80^{\circ}C$. Formed 5-HMF could be degraded to levulinic and formic acid at the presence of acid and water. Removal of water in reaction medium could prevent 5-HMF degradation.

• Journal of Korea Technical Association of The Pulp and Paper Industry
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• v.45 no.1
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• pp.27-34
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• 2013

Quantitative analysis of 5-hydroxymethylfufural (5-HMF) conversion from fructose by dehydration and rearrangement was investigated by $^1H$-NMR spectroscopic method. Fructose was converted to 5-HMF in dimethylsulfoxide (DMSO)-$d^6$ or acidic deuterium hydroxide at controlled reaction temperature and time. With addition of internal standards (biphenyl for DMSO-$d^6$ solvent, and 2,5-dihydroxybenzoic acid for deuterium oxide solvent), conversion from fructose to 5-HMF was analyzed by $^1H$-NMR spectroscopy. Quantitative analysis was run by comparison with peak area integration between of 5-HMF and internal standard. In DMSO solvent, 5-HMF was stable end product but part of 5-HMF was converted to formic and levulinic acid at acidic aqueous medium.

• Journal of the Korean Wood Science and Technology
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• v.44 no.5
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• pp.705-715
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• 2016

The main aim of this study was to investigate the potential of wood charcoal on removing furan compounds (5-hydroxymethylfurfural (5-HMF), furfural) known as fermentation inhibitors in sugar hydrolysates obtained from supercritical water treatment of lignocellulosic biomass. For this aim, model hydrolysate was prepared, and removal rates of sugars or furan compounds depending on wood charcoal concentration and treatment time were calculated and analyzed in comparison with the case of activated carbon. 0.5, 1, 2, 4, 8, or 12% (w/v) of wood charcoal or activated carbon was loaded into the model hydrolysate, containing glucose, xylose, 5-HMF, and furfural, and treatment was conducted for 1, 3, 6, 12, or 24 h. After treatment, removal rates of 5-HMF and furfural gradually increased as wood charcoal concentration or treatment time increased, and over 95% of 5-HMF and furfural were removed at 8% of wood charcoal concentration and 3 h of treatment time, while the loss of sugars (< 2%) was hardly observed. On the other hand, in the case of activated carbon treatment, removal rates of 5-HMF and furfural were over 95% at mild condition (activated carbon concentration: 8%, treatment time: 1 h), but over 10% of glucose and xylose were removed. Therefore, considering sugar production and further process applied sugar, the wood charcoal treatment of sugar hydrolysate was more effective for removing furan compounds and maintaining the sugar yield.

• Korean Chemical Engineering Research
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• v.60 no.2
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• pp.193-201
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• 2022

5-HMF(5-Hydroxymethylfurfural) and LA(levulinic acid) derived from biomass are green platform chemicals, which have a wide of potential applications as biofules and biochemicals. In this study, the kinetics of LA formation from glucose decomposition with various concentration of sulfuric acid at different temperature was investigated. The experiments were performed in a broad temperature (140-200 ℃), using H₂SO₄ (1-3 wt%) as the catalyst. Glucose solution was made by dissolving 1 g of glucose in 10 ml of H₂SO₄ solution. The reactions rates increased with temperature and the activation energy showed a similar tendency to previous reported values. Reaction time for maximum concentration of 5-HMF decreased as the temperature increased. Furthermore, the decomposition of 5-HMF was fast as the acid concentration increased. Reaction time to reach maximum concentration of levulinic acid was reduced as the acid concentration increased. Continuing to raise the temperature decreased the maximum concentration of levulinic acid and increased the amount of humins. On the basis of results, kinetic parameters help to understand mechanism of LA and 5-HMF. In addition, this study provides useful information to achieve high concentration of LA and 5-HMF from biomass.

• Clean Technology
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• v.20 no.2
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• pp.108-115
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• 2014

Various metal chlorides and acid catalysts in ionic liquid solvent were investigated to directly convert cellulose into 5-hydroxymethylfurfural (5-HMF). Metal chlorides containing Sn(II), Zn(II), Al(III), Fe(III), Cu(II), and Cr(III) were used and acidic ionic liquid immobilized on silica gel as an acid catalyst and commercial acid catalysts (sulfuric acid, chloric acid, Amberlyst-15,DOWEX50x8) were used for comparison studies. The acid strength and amount of acid catalysts were probed with Hammett indicator. The selectivity and yield of 5-HMF were determined with reaction temperature, reaction time and catalyst ratio. A catalyst containing $CrCl_3-6H_2O$ and $SiO_2-[ASBI]HSO_4$ showed the highest selectivity and it was found that this catalyst had higher activity than commercial solid acid catalysts such as Amberlyst-15 and DOWEX50x8. The selectivity of 5-HMF appeared to be mainly dependent on the acid strength and catalyst ratio, it was found that levulinic acid was produced from 5-HMF by rehydration.

• Journal of the Korean Wood Science and Technology
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• v.41 no.4
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• pp.287-292
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• 2013

Reaction of glucose and xylose to secondary hydrolysis of concentrated acid hydrolysis was quantitatively analyzed by $^1H$-NMR spectroscopic method. Anomeric hydrogen, furan and formic acid peaks were selected for quantitative analysis. The glucose was converted to the formic acid and the levulinic acid via the 5-hydroxymethylfurfural (HMF) but the xylose was converted to the fufural, which further degraded to the formic acid. The conversion to furans was slower for the glucose than the xylose. But the 5-HMF formed from the glucose was unstable in acidic aqueous medium, resulted in fast conversion to the levulinic acid and the formic acid. The furfural was relatively stable than 5-HMF at acidic aqueous medium.

• Applied Chemistry for Engineering
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• v.30 no.3
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• pp.280-289
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• 2019

5-hydroxymethylfurfural (HMF) and its derivatives, 2,5-furandicarboxylic acid (FDCA) or 2,5-diformylfuran (DFF), are regarded as the "sleeping giants" owing to their wide range of applications and a good alternative source for the production of significant chemicals in almost all kind of industries. This mini-review briefly covers the aspects related to the syntheses, transformation, and applications for the biomass-derived platform chemicals from past to most recent. Many scientific efforts have continuously been made to find out the environmental benign applicable ways in order to achieve the full advantage of these renewable materials because of not only to protect the globe but also shield the future of new generations. One of the best solutions could be the development and utilization of platform chemicals from the natural biomass.

• Food Science and Biotechnology
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• v.18 no.3
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• pp.717-723
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• 2009

Thermal degradation characteristics of sucrose was investigated. A 20% sucrose solution was heated to temperatures of $110-150^{\circ}C$ for 1-5 hr. Chromaticity, pH, organic acids, 5-hydroxymethylfurfural (HMF), free sugars, electron donating ability (EDA), and ascorbic acid equivalent antioxidant capacity (AEAC) of the heated sucrose solutions were evaluated. With increasing temperatures and times, the L-, a-, and b-values decreased; however, total color difference (${\Delta}E_{ab}$) increased. The pH and sucrose contents decreased, and fructose and glucose contents increased with increasing heating temperature and time. Organic acids, such as formic acid, lactic acid, and levulinic acid, and HMF contents increased with increasing heating temperatures and times. EDA (%) and the AEAC of the heated sucrose solutions increased with increasing heating temperature and time. The heated sucrose solution was more effective than unheated sucrose solution, having higher EDA (90 fold), and AEAC (13 fold).

• Journal of the Korean Society of Food Science and Nutrition
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• v.40 no.1
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• pp.84-88
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• 2011

Some thermally processed foods have higher biological activities due to their various chemical changes during heat treatment. Especially, 5-hydroxymethylfurfural (HMF) is derived from dehydration of sugars and has been identified in processed garlic. The biological function of HMF have revealed as antisickling agent and thyrosinase inhibitor. This study was carried out to examine the formation of HMF and free sugars from the aged garlics when it is treated at 60 and $75^{\circ}C$ and different incubation periods from 7 to 35 days. HMF and free sugars from the hot-water extracts of aged garlics were analyzed with GC/MS, LC/MS, and HPLC. The amount of HMF was higher than at $75^{\circ}C$ and increasing incubation period. Among free sugars, the only fructose except glucose and sucrose was formed and converted to HMF at high temperature and long incubation period. However, fructose formed in low temperature during making of aged garlic was rarely converted to HMF. This result indicates that formation of HMF can be dependent on the temperature and incubation period for making aged garlic.

• Food Science of Animal Resources
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• v.38 no.5
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• pp.995-1007
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• 2018

Changes in the physicochemical properties of ready-to-feed liquid infant formula (LIF) stored at different temperatures (10, 20, 30, and $40^{\circ}C$) for 6 mon, focusing on 5-hydroxymethylfurfural (HMF) content, color, pH, fat globule size distribution, and rheological properties were determined. The HMF content increased with storage time, and LIF stored at $40^{\circ}C$ had a higher HMF content than that of LIF stored at $10^{\circ}C$. The lightness ($L^*$) decreased while redness ($a^*$) and yellowness ($b^*$) increased with increasing HMF content. The fat globule size and pH of LIF stored at $10^{\circ}C$ did not change. However, in the case of LIF stored at $30^{\circ}C$ and $40^{\circ}C$, the fat globule size increased and the pH decreased during storage for 6 mon. LIF stored at $40^{\circ}C$ had a higher apparent viscosity (${\eta}_{a,10}$) than that of LIF stored at $10^{\circ}C$, and the shear-thinning behavior of LIF stored at higher temperature was stronger than that of LIF stored at low temperature. The physicochemical changes of LIF during storage were accelerated by Maillard reaction (MR) at higher storage temperatures. Therefore, even if LIF is aseptically manufactured, we recommend that sterilized LIF should be stored at low temperature in order to minimize quality changes during storage.