Rapid and selective retro-aldol condensation of glucose to glycolaldehyde in supercritical water

Sasaki, Mitsuru; Goto, Kohtaro; Tajima, Kiyohiko; Adschiri, Tadafumi; Arai, Kunio

doi:10.1039/b203968k

Cited by 174 publications

(149 citation statements)

References 14 publications

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“…This fact means that the concentrations of hydrogen and hydroxyl ions are high, and therefore, there is the possibility that the water can act as an acid or base catalyst without the addition of any further catalyst [6][7][8]. Based on this feature, the hydrolysis of vegetable oil [9] and degradation of polycyclic hydrocarbons [10] by water have been reported, as well as condensation [11] and isomerization [12] reactions.…”

Section: Introductionmentioning

confidence: 94%

Degradation of Pentoses and Hexouronic Acids in Subcritical Water

2007

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The degradation of arabinose, xylose, ribose and lyxose in subcritical water was measured at 200, 220 and 240°C. Ribose was the most rapidly degraded among the pentoses tested. The degradation of the glucuronic and galacturonic acids proceeded at lower temperatures than that of the pentoses, and was measured at 140, 150 and 160°C. The degradation processes of the pentoses and hexouronic acids could be expressed by the Weibull model, and the kinetic parameters were then estimated. The activation energy and frequency factor for the degradation of each substrate were estimated from the temperature dependence of the rate constant. The enthalpy-entropy compensation held for the degradation of the pentoses as well as the hexoses, which suggests that the degradation of the hexouronic acids proceeded through a mechanism different from that for the pentoses and hexoses. The molar yield of a pentose to furfural was ca. 0.3 at any temperature, irrespective of the pentose type. Acidic compounds were also formed from the pentoses in proportion to the amount of consumed substrates. The formation of acidic compounds resulted in a rapid decrease in pH.

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Section: Introductionmentioning

confidence: 94%

Degradation of Pentoses and Hexouronic Acids in Subcritical Water

2007

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“…[19] The Lobry-de Bruyn-van Ekenstein isomerization of glucose to fructose can be catalyzed by Lewis acidic Sn sites in zeolites. [19,24,40,49] The retro-aldol condensation of fructose then results in DHA and GLA, [19,50] which can easily be converted to methyl lactate with Sn-MWW. The results for the conversion of mono-and disaccharides in methanol to methyl lactate are summarized in Table 2.…”

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confidence: 99%

Highly Active and Recyclable Sn‐MWW Zeolite Catalyst for Sugar Conversion to Methyl Lactate and Lactic Acid

et al. 2013

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Not just sugar! Lewis‐acidic Sn‐MWW zeolites are obtained through postsynthesis functionalization of deboronated B‐MWW with Sn. These materials are highly active, selective, and recyclable catalysts for the conversion of triose sugars to methyl lactate (in methanol) and lactic acid (in water). They also demonstrate good performance in the conversion of hexose sugars and sucrose to methyl lactate.

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“…Then, various competitive reaction takes place, and it is not easy to obtain high yield of the target product. Sasaki et al studied retro-aldol condensation to produce glycolaldehyde from glucose [93].…”

Section: Carbon-carbon Bond Breakagementioning

confidence: 99%

Production of Chemicals in Supercritical Water

Matsumura

Yong

2014

Biofuels and Biorefineries

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Supercritical water (SCW) is expected to be a green solvent for dissolving substances, for chemical synthesis, or for chemical reactions, and thus various study has been carried out. Production of chemicals has been found possible in SCW. This chapter reviews the chemical production in terms of feedstocks and reactions. The feedstocks can include biomass (cellulose, hemicellulose and lignin), plastics, other wastes (e.g., tire, rubber), inorganics and waste water. The reactions include SCW gasification (where hydrolysis and pyrolysis take important roles), SCW oxidation, depolymerization, precipitation, hydrothermal synthesis, other organic reactions for synthesis of chemicals. In these reactions, roles of H 2 O are: (1) Reactant/product (hydrolysis, hydration, hydrogen source and freeradical chemistry) or catalyst (Acid/base catalyst precursor and catalyst in the transition state); (2) Intermolecular interactions in high temperature water: Solvation effects (effects of preferential solvation, hydrophobicity and solvent dynamics) and density inhomogeneity effects (ions, organic compounds, noble gases and radicals); (3) Medium: Energy transfer, diffusion and solvent cages and phase behavior. However, low selectivity and yield and high production cost are barriers for the commercialization of production of chemicals in SCW.

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Rapid and selective retro-aldol condensation of glucose to glycolaldehyde in supercritical water

Abstract: Retro-aldol condensation of glucose occurred preferentially relative to dehydration and isomerization under low water density conditions in supercritical water, and glycolaldehyde was successfully produced in a rapid and selective manner without any catalyst. DJM This journal is

Cited by 174 publications

References 14 publications

Degradation of Pentoses and Hexouronic Acids in Subcritical Water

Degradation of Pentoses and Hexouronic Acids in Subcritical Water

Highly Active and Recyclable Sn‐MWW Zeolite Catalyst for Sugar Conversion to Methyl Lactate and Lactic Acid

Production of Chemicals in Supercritical Water

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