3128-06-1Relevant articles and documents
Levulinic acid production from Cicer arietinum, cotton, Pinus radiata and sugarcane bagasse
Victor, Amudhavalli,Pulidindi, Indra Neel,Gedanken, Aharon
, p. 44706 - 44711 (2014)
Levulinic acid is a key platform chemical. Even gasoline range chemicals could be produced from levulinic acid making it a strategically significant compound. Producing levulinic acid from biomass is attractive from economic as well as environmental aspec
Selective glucose transformation by titania as a heterogeneous Lewis acid catalyst
Nakajima, Kiyotaka,Noma, Ryouhei,Kitano, Masaaki,Hara, Michikazu
, p. 100 - 105 (2014)
The Lewis acidity of phosphate-immobilized anatase TiO2 (phosphate/TiO2) has been studied to develop novel environmentally benign reaction systems. Fourier transform infrared (FT-IR) measurements suggested that most Lewis acid sites on bare and phosphate/TiO2 surface function even in water. phosphate/TiO2 exhibits high catalytic performance for selective 5-(hydroxymethyl)furfural (HMF) production from glucose in THF/water (90/10 vol.%) solution. This is attributed to water-tolerant Lewis acid sites on phosphate/TiO2 that promote step-wise conversion of glucose into HMF. The catalyst was easily recovered from reaction solution by simple decantation or filtration, and can be used repeatedly without significant loss of original activity for subsequent reactions.
Selective conversion of cellulose to hydroxymethylfurfural in polar aprotic solvents
Weingarten, Ronen,Rodriguez-Beuerman, Alexandra,Cao, Fei,Luterbacher, Jeremy S.,Alonso, David Martin,Dumesic, James A.,Huber, George W.
, p. 2229 - 2234 (2014)
Herein, we report a new reaction pathway to produce hydroxymethylfurfural (HMF) from cellulose under mild reaction conditions (140-190°C; 5 mM H 2SO4) in polar aprotic solvents (i.e. THF) without the presence of water. In this system, levoglucosan is the major decomposition product of cellulose, followed by dehydration to produce HMF. Glucose, levulinic acid, and formic acid are also produced as a result of side reactions with water, which is a by-product of dehydration. The turnover frequency for cellulose conversion increases as the water content in the solvent decreases, with conversion rates in THF being more than twenty times higher than those in water. The highest HMF yield from cellulose was 44% and the highest combined yield of HMF and levulinic from cellulose was 53%, which are nearly comparable to yields obtained in ionic liquids or biphasic systems. Moreover, the use of a low boiling point solvent, such as THF, facilitates recovery of HMF in downstream processes.
Solid acid-catalyzed cellulose hydrolysis monitored by in situ Atr-Ir spectroscopy
Zakzeski, Joseph,Grisel, Ruud J. H.,Smit, Arjan T.,Weckhuysen, Bert M.
, p. 430 - 437 (2012)
The solid acid-catalyzed hydrolysis of cellulose was studied under elevated temperatures and autogenous pressures using in situ ATR-IR spectroscopy. Standards of cellulose and pure reaction products, which include glucose, fructose, hydroxymethylfurfural (HMF), levulinic acid (LA), formic acid, and other compounds, were measured in water under ambient and elevated temperatures. A combination of spectroscopic and HPLC analysis revealed that the cellulose hydrolysis proceeds first through the disruption of the glycosidic linkages of cellulose to form smaller cellulose molecules, which are readily observed by their distinctive C-O vibrational stretches. The continued disruption of the linkages in these oligomers eventually results in the formation and accumulation of monomeric glucose. The solid-acid catalyst accelerated the isomerization of glucose to fructose, which then rapidly reacted under hydrothermal conditions to form degradation products, which included HMF, LA, formic acid, and acetic acid. The formation of these species could be suppressed by decreasing the residence time of glucose in the reactor, reaction temperature, and contact with the metal reactor. The hydrolysis of regenerated cellulose proceeded faster and under milder conditions than microcrystalline cellulose, which resulted in increased glucose yield and selectivity. Vibrating acids: The solid acid-catalyzed hydrolysis of cellulose has been studied by using in situ ATR-IR spectroscopy. It is possible to monitor the formation and consumption of important products and intermediates by their distinctive vibrational characteristics under the reaction conditions. Copyright
In situ NMR spectroscopy: Inulin biomass conversion in ZnCl2 molten salt hydrate medium - SnCl4 addition controls product distribution
Wang, Yingxiong,Pedersen, Christian Marcus,Qiao, Yan,Deng, Tiansheng,Shi, Jing,Hou, Xianglin
, p. 439 - 443 (2014)
The dehydration of inulin biomass to the platform chemicals, 5-hydroxymethylfurfural (5-HMF) and levulinic acid (LA), in ZnCl2 molten salt hydrate medium was investigated. The influence of the Lewis acid catalyst, SnCl4, on the produ
Synergistic catalytic effect of the ZnBr2-HCl system for levulinic acid production using microwave irradiation
Kumar, Vijay Bhooshan,Pulidindi, Indra Neel,Gedanken, Aharon
, p. 11043 - 11048 (2015)
A catalytic process for the selective conversion of carbohydrates to levulinic acid is developed. A synergy in the catalytic action is observed when a combination of ZnBr2 and HCl was used as the catalyst which is attributed to the in situ generation of HBr. Carbohydrates, namely, glucose, molasses and sucrose, were employed as feedstock for levulinic acid production. Microwave irradiation of glucose either in the presence of HCl alone or both HCl and ZnBr2 as catalysts yielded the formation of levulinic acid. But the conversion of glucose to levulinic acid was much faster (only 6 min) when both HCl and ZnBr2 were employed together. The effect of the reaction parameters like, the time of irradiation, % power, and amount of substrate and catalyst on the yield of levulinic acid were studied. The reaction products in each case were analysed using 1H and 13C NMR. The yield of levulinic acid was estimated using HPLC. The maximum yield of levulinic acid obtained from glucose was 53 wt%.
A new functionalized ionic liquid for efficient glucose conversion to 5-hydroxymethyl furfural and levulinic acid
Ramli, Nur Aainaa Syahirah,Amin, Nor Aishah Saidina
, p. 113 - 121 (2015)
The conversion of glucose to 5-hydroxymethyl furfural (5-HMF) and levulinic acid (LA) using ionic liquid is a promising method for producing liquid fuels from renewable resources. In this study, three types of acidic functionalized ionic liquids (FILs) were prepared and used as catalysts in the conversion of glucose to 5-HMF and LA. The prepared FILs were characterized using CHNS elemental analysis and 1H and 13C NMR. The acidity of the FILs was examined using pyridine-FTIR, Hammett and acid-base titration methods. The FIL with high acidity and with both Br?nsted and Lewis acid sites present seemed suitable for 5-HMF and LA production. Among the tested FILs, 1-sulfonic acid-3-methyl imidazolium tetrachloroferrate ([SMIM][FeCl4]) demonstrated the highest catalytic performance. The yields of 5-HMF and LA reached as high as 18% and 68%, respectively after 4 h at 150°C. The catalyst was reused five times without significant loss of activity. Furthermore, for the kinetic analysis performed for glucose conversion, the activation energy and pre-exponential factor for the reaction were 38 kJ mol-1 and 925 min-1, respectively. The experimental results demonstrated the potential of FIL as a catalyst for biomass transformation to platform chemicals under mild process condition.
5-Hydroxymethylfurfural and levulinic acid derived from monosaccharides dehydration promoted by InCl3 in aqueous medium
Shen, Yue,Sun, Jiankui,Yi, Yuxuan,Wang, Bo,Xu, Feng,Sun, Runcang
, p. 114 - 120 (2014)
Indium trichloride (InCl3) was used as catalyst for the conversion of monosaccharides into 5-hydroxymethylfurfural (5-HMF) and levulinic acid (LA) in aqueous medium. 5-HMF yield of 60% (10 min) and LA yield of 57% (60 min) were achieved from glucose at 180 °C with 2.5 mol% of InCl 3, and 5-HMF yield of 79% (15 min) and LA yield of 45% (60 min) were obtained from fructose under the same conditions. Moreover, the isomerization process between glucose and fructose was investigated through the comparative studies of glucose/fructose mixture with different ratios as substrates. It was found that InCl3 could not only catalyze the isomerization of glucose to fructose as well as the reverse direction, but also have the positive effects on the dehydration and conversion of monosaccharides. Based on this, a catalytic mechanism of dehydration of glucose and fructose promoted by InCl 3 was proposed.
Effect of NaCl on the conversion of cellulose to glucose and levulinic acid via solid supported acid catalysis
Potvin, Joshua,Sorlien, Erin,Hegner, Jessica,DeBoef, Brenton,Lucht, Brett L.
, p. 5891 - 5893 (2011)
Cellulose is hydrolyzed to glucose, which is further converted to levulinic acid in the presence of Nafion, as a surface supported acid catalyst. The addition of simple alkali metal halide salts, including NaCl, provides significant enhancement to the yield. The catalyst can be recycled suggesting possible extension into a continuous flow reactor for the synthesis of the biofuel precursors.
Conversion of hemicellulose into furfural using solid acid catalysts in γ-valerolactone
Gürbüz, Elif I.,Gallo, Jean Marcel R.,Alonso, David Martin,Wettstein, Stephanie G.,Lim, Wee Y.,Dumesic, James A.
, p. 1270 - 1274 (2013)
Hold the water: The hemicellulose fraction of lignocellulose can be converted into furfural in high yields (80 %) using solid acid catalysts (H-mordenite) in a monophasic system with γ-valerolactone (GVL) as the solvent. Furfural degradation reactions are decreased significantly when the water concentration in GVL is minimized, thus resulting in high furfural yields. Copyright
