10247-46-8Relevant academic research and scientific papers
Rates of spontaneous cleavage of glucose, fructose, sucrose, and trehalose in water, and the catalytic proficiencies of invertase and trehalas
Wolfenden, Richard,Yuan, Yang
, p. 7548 - 7549 (2008)
The half-lives for spontaneous hydrolysis of trehalose and sucrose at 25 °C are 6.6 × 106 years and 440 years. The half-lives for decomposition of the hydrolysis products glucose and fructose are 96 years and 70 days, respectively. Whereas sucrose and trehalose differ by a factor of 15000 in their rates of uncatalyzed hydrolysis, the reactions catalyzed by invertase (EC 3.2.1.26) and trehalase (EC 3.2.1.28) proceed at similar rates. Accordingly, the attainments of invertase as a catalyst are modest, but the rate enhancement and catalytic proficiency produced by trehalase approach the high levels achieved by polysaccharide hydrolases. Copyright
Glucose reactions with acid and base catalysts in hot compressed water at 473 K
Watanabe, Masaru,Aizawa, Yuichi,Iida, Toru,Aida, Taku M.,Levy, Caroline,Sue, Kiwamu,Inomata, Hiroshi
, p. 1925 - 1930 (2005)
The effects of the homogeneous catalysts (H2SO4 and NaOH) and heterogeneous catalysts (TiO2 and ZrO2) on glucose reactions were examined in hot compressed water (473 K) by a batch-type reactor. From the homogeneous catalyst studies, we confirmed that the acid catalyst promoted dehydration, while isomerization of glucose to fructose was catalyzed by alkali. Anatase TiO2 was found to act as an acid catalyst to promote formation of 5-hydroxymethylfuraldehyde (HMF). Zirconia (ZrO2) was a base catalyst to promote the isomerization of glucose. The effects of the additives were also confirmed through fructose reactions.
Kinetics of hydrolysis of fructooligosaccharides in mineral-buffered aqueous solutions: Influence of pH and temperature
L'Homme,Arbelot,Puigserver,Biagini, Anne
, p. 224 - 228 (2003)
High-performance anion exchange chromatography coupled with a pulsed amperometric detection system (HPAEC-PAD) was used to evaluate the extent of chemical hydrolysis of three fructooligosaccharides (FOS) including 1-kestose (β-D-Fru-(2→1)2-α-D-glucopyranoside, GF2), nystose (β-D-Fru-(2→1)3-α-D-glucopyranoside, GF3), and fructofuranosylnystose (β-D-Fru-(2→1)4-α-D-glucopyranoside, GF4). A kinetic study was carried out at 80, 90, 100, 110, and 120 °C in aqueous solutions buffered at pH values of 4.0, 7.0, and 9.0. Under each experimental condition, the determination of the respective amounts of reactants and hydrolysis products showed that FOS hydrolysis obeyed pseudo-first-order kinetics as the extent of hydrolysis, which decreased at increasing pH values, increased with temperature. The three oligomers were found to be degraded mainly under acidic conditions, and at the highest temperature value (120 °C), a quick and complete acid degradation of each FOS was observed. Using the Arrhenius equation, rate constants, half-life values, and activation energies were calculated and compared with those obtained from sucrose under the same experimental conditions. It appeared that the hydrolysis of FOS took place much more easily at acidic pH than at neutral or basic pH values.
Reaction kinetics and modeling of the enzyme-catalyzed production of lactosucrose using β-fructofuranosidase from Arthrobacter sp. K-1
Pilgrim, Axel,Kawase, Motoaki,Ohashi, Masayasu,Fujita, Koki,Murakami, Kazufumi,Hashimoto, Kenji
, p. 758 - 765 (2001)
Lactosucrose synthesis from sucrose and lactose was carried out by using β-fructofuranosidase from Arthrobacter sp. K-1. The transfructosylation mechanism was found to be of an ordered bi-bi type in which sucrose was bound first to the enzyme and lactosucrose was released last. Hydrolysis side-reaction experiments indicated that the reactions were uncompetitively inhibited by glucose and lactose, while no inhibition by fructose was apparent. The overall reaction rates were formulated. The reaction rate constants, equilibrium constant, and dissociation and Michaelis constants were determined at 35°C and 50°C by fitting the experimental concentration changes with the calculated values by a nonlinear least-square method. The average relative derivation for the concentrations was 9.67%. The kinetic parameters were also calculated for 43°C and 60°C by assuming the Arrhenius law, and the course of reaction was predicted. The obtained reaction rate equations well represented the concentration changes during the experiment at all temperatures.
Catalytic activity and stability of hydrophobic Mg-Al hydrotalcites in the continuous aqueous-phase isomerization of glucose into fructose
Delidovich,Palkovits
, p. 4322 - 4329 (2014)
The aqueous-phase isomerization of glucose into fructose, catalyzed by Mg-Al hydrotalcites, has been investigated under batch and continuous conditions. A commercial hydrotalcite with a hydrophobic surface modification and two hydrophilic hydrotalcites in carbonate form, or with OH- anions in the interlayer space, served as catalysts. With the hydrophobic hydrotalcite a lower conversion but superior selectivity to fructose could be demonstrated, reaching above 92% selectivity at 30% conversion. The observed by-products confirm retroaldolization of glucose and fructose as the main side reactions causing catalyst deactivation via adsorption. Additionally, acidic degradation products such as lactic acid cause neutralization of the hydrotalcites facilitating leaching of the Mg2+ ions. Fructose contributes a greater extent to by-product formation. Applying continuous operation conditions, fructose is removed from the reaction mixture. Therefore, by-product formation is notably suppressed and catalyst stability increases. During 70 to 100 h time-on-stream a slow deactivation of the hydrophobic hydrotalcite occurs. Regeneration can be achieved via calcination and treatment in an aqueous sodium n-dodecyl sulfate solution to introduce dodecyl sulfate anions to the interlayer space of the hydrotalcite, restoring the hydrophobic material properties.
Insights into the Kinetics and Reaction Network of Aluminum Chloride-Catalyzed Conversion of Glucose in NaCl-H2O/THF Biphasic System
Tang, Jinqiang,Zhu, Liangfang,Fu, Xing,Dai, Jinhang,Guo, Xiawei,Hu, Changwei
, p. 256 - 266 (2017)
We performed a systematic experimental kinetics study on AlCl3-catalyzed conversion of glucose to 5-hydroxymethylfurfural (HMF) in NaCl-H2O/tetrahydrofuran (THF) biphasic solvent. The kinetics model covers an extensive reaction network including the parallel and tandem reactions of isomerization, dehydration, decomposition, and polymerization from glucose. The accuracy of the model was verified by a parity plot and statistical significance analysis of the kinetic parameters. A deliberate insight into the intrinsic kinetic properties (reaction rate constant and apparent activation energy) of each subreaction elaborates the regulatory role of THF and NaCl on reaction pathways within the network. That is, THF suppresses the rehydration, degradation, and polymerization of HMF to unwanted byproducts, inhibits fructose-to-HMF dehydration and fructose-to-humins polymerization, but promotes the generation of formic acid (FA) from the direct degradation of both glucose and fructose by facilitating the generation of [Glc/Fru + H-H2O-FA]+ species without formation of levulinic acid (LA); while NaCl promotes the dehydration and polymerization of fructose, decelerates the glucose-to-fructose isomerization, and effectively suppresses glucose-to-humins polymerization. The suppression role of NaCl on glucose conversion may come from the inhibition on mutarotation and ring opening from glucose due to the existence of a hydrogen bond between (C6)O-H on glucose and Cl- ion. The Br?nsted acid (HCl) from the hydrolysis of AlCl3 is responsible for direct glucose/fructose-to-FA degradation, HMF-to-humins polymerization, and HMF-to-FA/LA rehydration. The Lewis acidic [Al(OH)2(aq)]+ species is active for the reversible glucose-to-fructose isomerization and direct HMF-to-FA degradation, whereas glucose/fructose-to-humins polymerization and fructose-to-HMF dehydration are both Br?nsted and Lewis acid-catalyzed. This work highlights a deep understanding of the complicated reaction network in the acid-catalyzed conversion of glucose to HMF in a biphasic solvent.
Structures of acylated sucroses from the flower buds of Prunus mume
Fujimoto, Katsuyoshi,Nakamura, Seikou,Matsumoto, Takahiro,Ohta, Tomoe,Yoshikawa, Masayuki,Ogawa, Keiko,Kashiwazaki, Eri,Matsuda, Hisashi
, p. 481 - 487 (2014)
Seven new acylated sucroses, mumeoses P-V, were isolated from the flower buds of Prunus mume, cultivated in Zhejiang province, China. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. Moreover, mumeoses C, D,
A Chromium Hydroxide/MIL-101(Cr) MOF Composite Catalyst and Its Use for the Selective Isomerization of Glucose to Fructose
Guo, Qiang,Ren, Limin,Kumar, Prashant,Cybulskis, Viktor J.,Mkhoyan, K. Andre,Davis, Mark E.,Tsapatsis, Michael
, (2018)
A metal–organic framework (MOF)-based catalyst, chromium hydroxide/MIL-101(Cr), was prepared by a one-pot synthesis method. The combination of chromium hydroxide particles on and within Lewis acidic MIL-101 accomplishes highly selective conversion of gluc
The effects of emulsion on sugar dehydration to 5-hydroxymethylfurfural in a biphasic system
Teong, Siew Ping,Yi, Guangshun,Zeng, Huaqiang,Zhang, Yugen
, p. 3751 - 3755 (2015)
Alkyl/amino functionalized silica nanoparticles to create an emulsion in a biphasic system for sugar dehydration to HMF were successfully developed. As a proof-of-concept, more than 10% increase of HMF yield and 20% increase of selectivity were achieved for both fructose and glucose dehydrations in the emulsion system as compared to the conventional biphasic system. The excellent recyclability of the nanoparticles also further widens the potential of the biphasic system to be scaled up for industrial application.
Effect of Tetrahydrofuran on the Solubilization and Depolymerization of Cellulose in a Biphasic System
Jiang, Zhicheng,Zhao, Pingping,Li, Jianmei,Liu, Xudong,Hu, Changwei
, p. 397 - 405 (2018)
The dissolution of cellulose from biomass is a crucial but complicated issue for maximizing the utilization of biomass resources to produce valuable chemicals, because of the extreme insolubility of cellulose. A biphasic NaCl–H2O–tetrahydrofuran (THF) system was studied, in which most of the pure microcrystalline cellulose (M-cellulose, 96.6 % conversion at 220 °C) and that contained in actual biomass were converted. Nearly half of the O6?H???O3 intermolecular hydrogen bonds could be broken by THF in the H2O–THF co-solvent system, whereas the cleavage of O2?H???O6 intramolecular hydrogen bonds by H2O was significantly inhibited. In the NaCl–H2O–THF system, THF could significantly promote the effects of both H2O and NaCl on the disruption of O2?H???O6 and O3?H???O5 intramolecular hydrogen bonds, respectively. In addition, THF could protect and transfer the cellulose-derived products to the organic phase by forming hydrogen bonds between the oxygen atom in THF and the hydrogen atom of C4?OH in the glucose or aldehyde group in 5-hydroxymethylfurfural (HMF), which can lead more NaCl to combine with the -OH of M-cellulose and further disrupt hydrogen bonding in M-cellulose, thereby improving the yield of small molecular weight products (especially HMF) and further promoting the dissolution of cellulose. As a cheap and reusable system, NaCl–H2O–THF system may be a promising approach for the dissolution and further conversion of cellulose in lignocellulosic biomass without any enzymes, ionic liquids, or conventional catalysts.
