Reactions of d-fructose in water at temperatures up to 400°C and pressures up to 100MPa

Aida, Taku Michael; Tajima, Kiyohiko; Watanabe, Masaru; Saito, Yuki; Kuroda, Kiyoshi; Nonaka, T.; Hattori, Hideo; Smith, Richard L.; Arai, Kunio

doi:10.1016/j.supflu.2006.12.017

Cited by 151 publications

(94 citation statements)

References 24 publications

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“…The minor product glyceraldehyde is likely formed from D-fructose via a retro-aldol condensation [30,48]. It is known to react further to pyruvaldehyde and subsequently to lactic acid [30,[51][52][53]. Also, minor amounts of furfural are detected in the reaction and likely originate from D-fructose [48,51].…”

Section: Exploratory Experiments On the Conversion Of Inulin To Hmf Umentioning

confidence: 99%

Experimental and Modeling Studies on the Conversion of Inulin to 5-Hydroxymethylfurfural Using Metal Salts in Water

2015

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Inulin, a plant polysaccharide consisting of mainly D-fructose units, is considered an interesting feed for 5-hydroxymethylfurfural (HMF), a top 12 bio-based chemical. We here report an exploratory experimental study on the use of a wide range of homogeneous metal salts as catalysts for the conversion of inulin to HMF in water. Best results were obtained using CuCl2. Activity-pH relations indicate that the catalyst activity of CuCl2 is likely related to Lewis acidity and not to Brönsted acidity. The effects of process conditions on HMF yield for CuCl2 were systematically investigated and quantified using a central composite design (160-180 °C, an inulin loading between 0.05 and 0.15 g/mL, CuCl2 concentration in range of 0.005-0.015 M, and a reaction time between 10 and 120 min). The highest experimental HMF yield in the process window was 30.3 wt. % (39 mol %, 180 °C, 0.05 g/mL inulin, 0.005 M CuCl2 and a reaction time of 10 min). The HMF yields were modelled using non-linear, multi variable regression and good agreement between experimental data and model were obtained.

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Section: Exploratory Experiments On the Conversion Of Inulin To Hmf Umentioning

confidence: 99%

Experimental and Modeling Studies on the Conversion of Inulin to 5-Hydroxymethylfurfural Using Metal Salts in Water

2015

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“…It involves the saccharification of inulin to the monomeric building blocks (d-fructose and some d-glucose), followed by the reaction of these C6 sugars to HMF. The latter is not inert under reaction conditions and reacts further to LA and FA [18,19,[49][50][51][52].…”

Section: Hmf Synthesis From Inulin In the Absence Of A Catalystmentioning

confidence: 99%

Experimental and modelling studies on the uncatalysed thermal conversion of inulin to 5-hydroxymethylfurfural and levulinic acid

Fachri

Abdilla

Rasrendra

et al. 2015

Sustain Chem Process

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Background: 5-Hydroxymethylfurfural (HMF), an important biobased platform chemical, is accessible by the acid catalysed conversion of biopolymers containing hexoses (cellulose, starch, inulin) and monomeric sugars derived thereof. We here report an experimental study on the uncatalysed, thermal conversion of inulin to HMF in aqueous solutions in a batch set-up. Results:The reactions were conducted in a temperature range of 153-187°C, an inulin loading between 0.03 and 0.12 g/mL and batch times between 18 and 74 min using a central composite experimental design. The highest experimental HMF yield in the process window was 35 wt% (45 mol%), which is 45% of the theoretical maximum (78 wt%). The HMF yields were modeled using a statistical approach and good agreement between experiment data and model was obtained. The possible autocatalytic role of formic acid (FA) and levulinic acid, two main byproducts, was probed by performing reactions in the presence of these acids and it was shown that particularly FA acts as a catalyst. Conclusions:Inulin is an interesting feed for the synthesis of HMF in water. A catalyst is not required, though autocatalytic effects of FA play a major role and also affect reaction rates and product yields. Graphical abstract:Chicory 5-hydroxymethylfurfural No catalystInulin

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“…Furthermore Jacobsen and Wyman [29] showed that hydrothermal conversion of hemicellulose involves a similar hydrolytic reaction pathway than for cellulose with a higher reactivity due to the amorphous hemicellulose structures. Studies on the hydrothermal conversion of pentose and hexose monosaccharides show that they exhibit both similar reactivities [15][16][17]. They are simultaneously dehydrated to form substituted aromatic compounds such as furan and benzentriol and also fragmented by retro-aldol splitting to mainly oxygenated aliphatic compounds such as hydroxycarbonyls and carboxylic acids.…”

Section: Reaction Pathwaymentioning

confidence: 99%

“…The approach that can be carried out to simplify the reaction pathway investigation consists in studying transformation of compounds representative of lignocellulosic constituents (i.e. saccharidic and phenolic compounds) [15][16][17][18][19][20][21][22][23][24]. Nevertheless, hydrothermal conversion of lignocellulosic model compounds, even from simple compounds such as glucose or catechol, generates also complex mixtures of products whose complete characterization is an analytical challenge.…”

Section: Introductionmentioning

confidence: 99%

Correspondence Between Structure and Reactivity During Hydrothermal Conversion of Lignocellulosic Macromolecules

Barbier

Charon

Dupassieux

et al. 2013

Oil Gas Sci. Technol. – Rev. IFP Energies nouvelles

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Re´sume´-Relation entre la structure et la re´activite´en conversion hydrothermale des macromole´cules de lignocellulosique -Ce travail porte sur l'e´tude des voies re´actionnelles accompagnant la lique´faction thermochimique du bois et de ses constituants lignocellulosiques lors d'un traitement hydrothermal. Pour ce faire, une approche analytique multi-technique originale combinant des me´thodes chromatographiques et spectroscopiques comple´mentaires a e´te´de´veloppe´e afin de caracte´riser les structures et les masses mole´culaires des produits. Les re´sultats obtenus montrent que la fraction holocellulosique et la fraction ligneuse de la biomasse ont des re´activite´s tre`s diffe´rentes. Bien que les deux mate´riaux re´agissent selon des sche´mas re´actionnels complexes faisant intervenir de nombreuses voies de fragmentation et de condensation compe´titives, la fraction holocellulosique re´agit par une premie`re e´tape de fragmentation suivie de la condensation des fragments ge´ne´re´s alors que la lignine re´agit principalement par de´polyme´risation partielle. Au cours de la lique´faction de la biomasse lignocellulosique, les compose´s provenant de la transformation des fractions holocellulosique et ligneuse se trouvent en contact les uns avec les autres dans le milieu hydrothermal et re´agissent ensemble pour former des produits de condensation.Abstract -Correspondence Between Structure and Reactivity During Hydrothermal Conversion of Lignocellulosic Macromolecules -In this study, reaction pathway of a woody biomass under hydrothermal conditions is investigated in order to further understand reactions that occur during the thermochemical liquefaction of a lignocellulosic biomass. A multitechnique analytical approach combining chromatographic and spectroscopic techniques has been developed in order to characterize both chemical structure and molecular weight of the products. From our experiments, we can assume that the holocellulosic and the ligneous fractions of biomass have different reactivity under hydrothermal condition. Although hydrothermal conversion of holocellulose and lignin occur both according to a complex pathway composed of competitive fragmentation and condensation reactions, holocellulose reacts first by total fragmentation to low molecular weight compounds followed by the condensation of the fragment to heavy molecular weight compounds, whereas lignin reacts essentially

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Reactions of d-fructose in water at temperatures up to 400°C and pressures up to 100MPa

Cited by 151 publications

References 24 publications

Experimental and Modeling Studies on the Conversion of Inulin to 5-Hydroxymethylfurfural Using Metal Salts in Water

Experimental and Modeling Studies on the Conversion of Inulin to 5-Hydroxymethylfurfural Using Metal Salts in Water

Experimental and modelling studies on the uncatalysed thermal conversion of inulin to 5-hydroxymethylfurfural and levulinic acid

Correspondence Between Structure and Reactivity During Hydrothermal Conversion of Lignocellulosic Macromolecules

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