Effect of Lewis and Brønsted acidity on glucose conversion to 5-HMF and lactic acid in aqueous and organic media

Marianou, Asimina A.; Michailof, Chrysoula M.; Pineda, Antonio; Iliopoulou, Eleni F.; Triantafyllidis, Konstantinos S.; Lappas, Angelos A.

doi:10.1016/j.apcata.2018.01.029

Cited by 149 publications

(81 citation statements)

References 74 publications

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“…Owing to its instability, 5‐HMF requires careful tuning of the reaction parameters and/or a continuous extraction process to ensure high yields. The instability of 5‐HMF and the possibility of forming humins and other side products often leads to modest yields, which typically range from 20 to 70 % . Here, the yield of 5‐HMF was determined by 1 H NMR spectroscopy with CH 2 Br 2 as internal standard, and the identity of the product was further confirmed by GC‐MS (see Experimental Section and Figures S6–S9 for representative 1 H NMR spectra).…”

Section: Resultsmentioning

confidence: 92%

“…The instability of 5-HMF and the possibilityo ff orming huminsa nd other side products often leads to modesty ields, which typically range from 20 to 70 %. [49][50][51][52][53][54][55][56] Here, the yield of 5-HMF was determined by 1 HNMR spectroscopy with CH 2 Br 2 as internal standard, and the identity of the productw as further confirmed by GC-MS (see Experimental Sectiona nd FiguresS6-S9 for representative 1 HNMR spectra). At temperatures below 165 8C, no reaction was observed, and 5-HMF only started to form at 165 8C( Table 2, entries 1-3).…”

Section: Catalytic Evaluation Of Leathermentioning

confidence: 99%

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Leather‐Promoted Transformation of Glucose into 5‐Hydroxymethylfurfural and Levoglucosenone

et al. 2019

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Section: Resultsmentioning

confidence: 92%

Section: Catalytic Evaluation Of Leathermentioning

confidence: 99%

Leather‐Promoted Transformation of Glucose into 5‐Hydroxymethylfurfural and Levoglucosenone

et al. 2019

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“…Although TiO 2 is not an effective catalyst for glucose conversion, phosphorylated TiO 2 exhibited excellent activity with a 5‐HMF yield of 81.2% . In the presence of Al 2 O 3 , 11.37% of 5‐HMF yield and 11.08% of fructose yield with 52.36% glucose conversion were got (Entry 5), agreeing well with the result reported by Marianou …”

Section: Resultsmentioning

confidence: 95%

“…confirmed that the synergistic effect of Lewis and Brönsted acid in a series of sulfonic‐acid‐functionalized ionic liquid (IL)‐heteropolyacid hybrid catalysts could significantly promote glucose conversion to 5‐HMF. Sn promoted solid catalysts including γ‐Al 2 O 3 , zeolites (ZSM‐5 and Beta) or mesoporous aluminosilicates (Al‐MCM‐41), and Sn δ+ as ion‐exchange cations on the above zeolites are also proved to be with the synergistic effect . Ordomsky et al .…”

Section: Introductionmentioning

confidence: 99%

Al₂O₃‐TiO₂ Modified Sulfonated Carbon with Hierarchically Ordered Pores for Glucose Conversion to 5‐HMF

Zhou

Wang

et al. 2019

ChemistrySelect

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Sulfonated carbons with hierarchically ordered pores (SCHOP) are not effective catalysts for glucose to 5‐hydroxymethylfurfural (5‐HMF) although they are very effective for fructose conversion due to insufficient and unsuitable Lewis acid sites in SCHOP unfavorable for isomerization of glucose to fructose. This paper attempts to intensify the Lewis acid sites on the surface of SCHOP by doping Al2O3 and TiO2 (Al−Ti@SCHOP) so as to promote glucose conversion to 5‐HMF. Characterizations by SEM, TEM, BET and N2 adsorption‐desorption showed that the well‐ordered hierarchical pore structure of SCHOP was preserved after doping the metal oxides. EDS and XRD analyses confirmed that Al2O3 and TiO2 were well‐dispersed on the surface. FTIR, Py‐FTIR and NH3‐TPD proved that not only sulfonic acid groups were introduced successfully but also very strong acid sites were formed. Furthermore, the strength of Lewis and Brönsted acid sites on the surface of Al−Ti@SCHOP were tailored by adjusting the mass ratio of Al2O3 to TiO2. Al−Ti@SCHOP with an Al2O3/TiO2 mass ratio of 2:1 demonstrated the highest catalytic activity for glucose dehydration to 5‐HMF. As high as above 96% of 5‐HMF selectivity could be obtained within the initial reaction time of 3.0 h, and a maximum 5‐HMF yield of 57.36% occurred at the reaction time of 5.0 h when reacting at 130 °C. Besides, the catalyst has its good stability.

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“…[46][47][48] However, this reaction could not have profound effect on furfural production. 37,38 When compared with IL3 and IL4 that had larger proportion of FeCl 3 , IL1 and IL2 had higher selectivity for oxygenated aliphatics. A low furfural yield of 44% was achieved.…”

Section: Effects Of Catalyst Composition On Liquid-phase Product DImentioning

confidence: 99%

Dehydration of xylose to furfural in butanone catalyzed by Brønsted‐Lewis acidic ionic liquids

Zhao

et al. 2019

Energy Science & Engineering

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In this study, the most abundant C5 carbohydrate unit in biomass, namely xylose, was chosen as the feedstock, and its hydrothermal conversion for furfural production was carried out in a green and renewable solvent system composed of water and butanone, in order to study the role of FeCl3 and [bmim]Cl of ionic liquid catalyst in the conversion process of xylose. A key intermediate named xylulose from Lewis acid‐catalyzed xylose isomerization was quantified. It was concluded that appropriate content of FeCl3 and [bmim]Cl favored the isomerization‐dehydration reaction path along which xylose was converted into furfural, while excessive amount of either component would result in side reactions leading to furfural consumption at long reaction times. By comparison between ionic liquid catalysts that had different active metal sites, xylose conversion and furfural yields were found to increase when the Lewis acidity of the metal ions became stronger. Moreover, chlorometallate anions with better catalytic performance than the original neutral salts were formed during catalyst preparation, and in this way, the xylose conversion and furfural formation were further promoted. Finally, the optimized ionic liquid catalyst produced a highest furfural yield of 75% and xylose conversion of 99% at 140°C.

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Effect of Lewis and Brønsted acidity on glucose conversion to 5-HMF and lactic acid in aqueous and organic media

Cited by 149 publications

References 74 publications

Leather‐Promoted Transformation of Glucose into 5‐Hydroxymethylfurfural and Levoglucosenone

Leather‐Promoted Transformation of Glucose into 5‐Hydroxymethylfurfural and Levoglucosenone

Al₂O₃‐TiO₂ Modified Sulfonated Carbon with Hierarchically Ordered Pores for Glucose Conversion to 5‐HMF

Dehydration of xylose to furfural in butanone catalyzed by Brønsted‐Lewis acidic ionic liquids

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Effect of Lewis and Brønsted acidity on glucose conversion to 5-HMF and lactic acid in aqueous and organic media

Cited by 149 publications

References 74 publications

Leather‐Promoted Transformation of Glucose into 5‐Hydroxymethylfurfural and Levoglucosenone

Leather‐Promoted Transformation of Glucose into 5‐Hydroxymethylfurfural and Levoglucosenone

Al2O3‐TiO2 Modified Sulfonated Carbon with Hierarchically Ordered Pores for Glucose Conversion to 5‐HMF

Dehydration of xylose to furfural in butanone catalyzed by Brønsted‐Lewis acidic ionic liquids

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Al₂O₃‐TiO₂ Modified Sulfonated Carbon with Hierarchically Ordered Pores for Glucose Conversion to 5‐HMF