7425-74-3Relevant academic research and scientific papers
Production of solubilized carbohydrate from cellulose using non-catalytic, supercritical depolymerization in polar aprotic solvents
Ghosh, Arpa,Brown, Robert C.,Bai, Xianglan
supporting information, p. 1023 - 1031 (2016/02/27)
We report yields of solubilized and depolymerized carbohydrate from solvent processing of cellulose as high as 94% without use of catalysts. Cellulose was converted using a variety of polar aprotic solvents at supercritical conditions, including 1,4-dioxane, ethyl acetate, tetrahydrofuran, methyl iso-butyl ketone, acetone, acetonitrile, and gamma-valerolactone. Maximum yield of solubilized products from cellulose, defined as both depolymerized carbohydrate and products of carbohydrate dehydration, was 72 to 98% at 350 °C for reaction times of 8-16 min. In all cases solvents were recovered with high efficiency. Levoglucosan was the most prevalent solubilized carbohydrate product with yields reaching 41% and 34% in acetonitrile and gamma-valerolactone, respectively. Levoglucosan yields increased with increasing polar solubility parameter, corresponding to decreasing activation energy for cellulose depolymerization.
Glucose dehydration to 5-hydroxymethylfurfural by a combination of a basic zirconosilicate and a solid acid
Yue, Chaochao,Rigutto, Marcello S.,Hensen, Emiel J. M.
, p. 2121 - 2128 (2015/02/19)
A recently reported layered zirconosilicate Na2ZrSi4O11 displays good activity in the isomerization of glucose to fructose in water at mild conditions. Part of the activity derives from the homogeneous base-catalyzed reaction due to exchange of the sodium ions of the layered zirconosilicate in water. Following ion-exchange, the isomerization is mainly catalyzed by the basic sites of the re-used heterogeneous zirconosilicate catalyst. Combined with the solid acid Amberlyst-15, 5-hydroxymethylfurfural (5-HMF) can be produced from glucose in a one-pot reaction. In a THF/H2O mixture solvent system, 5-HMF was obtained with 45 % selectivity at 87 % glucose conversion at a temperature of 180 °C in 1.5 h. Graphical Abstract: [Figure not available: see fulltext.]
Syntheses of 5-hydroxymethylfurfural and levoglucosan by selective dehydration of glucose using solid acid and base catalysts
Ohara, Mika,Takagaki, Atsushi,Nishimura, Shun,Ebitani, Kohki
scheme or table, p. 149 - 155 (2010/10/21)
Selective dehydration of glucose, the most abundant monosaccharide, was examined using a solid acid catalyst individually or a combination of solid acid and base catalysts to form anhydroglucose (levoglucosan) or 5-hydroxymethylfurfural (HMF), respectively. Glucose was dehydrated to anhydroglucose by acid catalysis in polar aprotic solvents including N,N-dimethylformamide. Amberlyst-15, a strongly acidic ion-exchange resin, functioned as an efficient solid acid catalyst for anhydroglucose production with high selectivity. In the presence of solid base, aldose-ketose isomerization of glucose to fructose preferentially occurred by base catalysis, even in coexistence with the solid acid, resulting in successive dehydration of fructose to 5-hydroxymethylfurfural by acid catalysis with high yield in a one-pot reaction. A combination of Amberlyst-15 and hydrotalcite, an anionic layered clay, afforded high HMF selectivity under a moderate reaction temperature, owing to prevention of anhydroglucose formation.
Thermochemical transformation of glucose to 1,6-anhydroglucose in high-temperature steam
Sasaki, Masahide,Takahashi, Kenji,Haneda, Yui,Satoh, Hiroe,Sasaki, Akiyoshi,Narumi, Atsushi,Satoh, Toshifumi,Kakuchi, Toyoji,Kaga, Harumi
, p. 848 - 854 (2008/09/16)
An aqueous solution of glucose was reacted at temperatures from 200 to 400 °C under atmospheric pressure using a continuous flow reactor. For reaction temperatures above 300 °C, the liquid product yield was not sensitive to the temperature change; on the other hand, below 300 °C, it decreased rapidly with decreasing temperature. 1,6-Anhydro-β-d-glucopyranose (AGP) and 1,6-anhydro-β-d-glucofuranose (AGF) were the major components in the liquid product. The yields of AGP and AGF were 40% and 19%, respectively, at 360 °C and a feed rate of 0.5 mL/min. The optimum space time to produce AGP and AGF was about 0.2-0.4 s under the present temperature conditions.
Pyrolysis of inulin, glucose, and fructose
Ponder, Glenn R.,Richards, Geoffrey N.
, p. 341 - 360 (2007/10/02)
The pyrolytic behavior of inulin, a (2->1)-linked fructofuranan, is described.Parallel investigations of the pyrolysis of glucose and of fructose were conducted to supplement the inulin results and to aid comparison with previous results from glucans.Effects of neutral and basic additives are emphasized.As with glucans, the addition of such additives (especially basic) increases the yields of the one-, two-, and three-carbon products (as well as of hexosaccharinolactones), while generally decreasing the yields of anhydro sugar and furan derivatives.The former products include glycolaldehyde, acetol, dihydroxyacetone, acetic acid, formic acid, and lactic acid.Mechanistic speculations are made regarding the origins of these compounds, as well as of furan derivatives and saccharinic acid lactones.Parallels with alkaline degradation are considered.
THE REVERSION REACTIONS OF D-GLUCOSE DURING THE HYDROLYSIS OF CELLULOSE WITH DILUTE SULFURIC ACID
Helm, Richard F.,Young, Raymond A.,Conner, Anthony H.
, p. 249 - 260 (2007/10/02)
The reversion product formed during the acid hydrolysis of Avicel to D-glucose, under conditions envisaged for the industrial conversion of woody biomass into monomeric sugars, have been determined by using gas-liquid chromatography.Avicel was hydrolyzed in dilute sulfuric acid (0.26-1.27 wt.percent) between 160 and 250 deg in small (3mm, i.d.) glass tubes at a 3:1 liquid-to-solid ratio.The anhydro sugars, levoglucosan and 1,6-anhydro-β-D-glucofuranose, were produced in the ratio of 7:3 and constituted >50percent of the total yield of reversion products.The yield of anhydro sugar followed equilibrium kinetics, and reached 6percent at maximum yields (50percent) of D-glucose.Isomaltose and gentiobiose were the most preponderant disaccharides found among the reversion products, constituting together ca. 25percent of the reversion products.The (1->2)- and (1->3)-linked α-disaccharides preponderated over their β counterparts.The total yields of reversion products approached 10percent on the basis of the D-glucose theoretically available.
CHARACTERIZATION OF MONO- AND OLIGOSACCHARIDES PRODUCED BY CO2 LASER IRRADIATION ON CELLULOSE
Suzuki, Jun,Azuma, Jun-ichi,Koshijima, Tetsuo,Okamura, Keizo,Okamoto, Hajime
, p. 481 - 484 (2007/10/02)
The chemical structures of three mono-, two di-, and two trisaccharides (1 - 7) isolated from the pyrolysis products formed by CO2 laser irradiation on cellulose were investigated.
