Efficient oxidation of monosaccharides to sugar acids under neutral condition in flow reactors with gold-supported activated carbon catalysts

doi:10.1007/s11705-024-2457-6

2024, Vol. 18

Issue (9) : 106 https://doi.org/10.1007/s11705-024-2457-6

Efficient oxidation of monosaccharides to sugar acids under neutral condition in flow reactors with gold-supported activated carbon catalysts

Ziqin Gong¹, Zengyong Li², Xu Zeng¹, Fengxia Yue¹, Wu Lan¹(

), Chuanfu Liu¹(

)

¹. State Key Laboratory of Pulp and Paper Engineering, School of Light Industry & Engineering, South China University of Technology, Guangzhou 510640, China
². Anhui Provincial Engineering Center for High Performance Biobased Nylons, School of Materials and Chemistry, Anhui Agricultural University, Hefei 230036, China

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Abstract

A significant reaction in the synthesis of biomass-based chemicals is the catalyst-based and targeted oxidation of monosaccharides into valuable sugar acids. In this study, an activated carbon supported gold catalyst was used to oxidize glucose and xylose to gluconic acid and xylonic acid under neutral condition. Optimization of reaction conditions for the catalysts was performed using both a batch reactor and a flow-through reactor. In a batch reactor, the yields of gluconic and xylonic acid reached 93% and 92%, respectively, at 90 °C within 180 min. In a flow reactor, both reactions reached a similar yield at 80 °C with the weight hourly space velocity of 47.1 h^–1. The reaction kinetics were explored in the flow reactor. The oxidation of glucose and xylose to gluconic and xylonic acid followed a first-order kinetics and the turnover frequency was 0.195 and 0.161 s^–1, respectively. The activation energy was evaluated to be 60.58 and 59.30 kJ·mol^–1, respectively. This study presents an environmentally friendly and feasible method for the selective oxidation of monosaccharides using an activated carbon supported gold catalyst, benefiting the high-value application of carbohydrates.

Keywords monosaccharides oxidation gluconic acid xylonic acid flow reactor kinetics

Corresponding Author(s): Wu Lan,Chuanfu Liu

Just Accepted Date: 19 April 2024 Issue Date: 17 June 2024

Cite this article:

Ziqin Gong,Zengyong Li,Xu Zeng, et al. Efficient oxidation of monosaccharides to sugar acids under neutral condition in flow reactors with gold-supported activated carbon catalysts[J]. Front. Chem. Sci. Eng., 2024, 18(9): 106.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-024-2457-6
https://academic.hep.com.cn/fcse/EN/Y2024/V18/I9/106

Scheme1 The process of preparing the Au/AC catalyst. PVA, polyvinyl alcohol; NPs, nanoparticles.

Fig.1 Morphology characterization of Au/AC catalyst. (a, b) SEM image of Au/AC. (c, d) TEM image of Au/AC at different magnifications. Inset histogram shows Au NPs size distribution. (e) High-resolution TEM image with an inset showing diffraction of Au NP. (f) The elemental mapping images. SEM, scanning electron microscopy; TEM, transmission electron microscopy; NP, nanoparticle.

Fig.2 Crystalline and surface electronic structure characterization. (a) XRD pattern; (b) N₂ adsorption-desorption isotherm and BET plot (inset); (c) the wide XPS survey spectra; (d) C 1s, (e) O 1s, and (f) Au 4f spectra of high resolution XPS. XRD, X-ray diffraction; XPS, X-ray photoelectron spectroscopy.

Fig.3 Chemical reaction equation for the oxidation of xylose and the conversion and yield of xylose oxidation to xylonic acid by Au/AC at different reaction temperatures, reaction time, catalyst dosages, and O₂ pressures (general reaction condition: 150 mg of xylose, 25 mL of H₂O). (a) 180 min, 50 mg of Au/AC, and 5 bars O₂; (b) 90 °C, 50 mg of Au/AC, and 5 bars O₂; (c) 90 °C, 180 min, and 5 bars O₂; (d) 90 °C, 180 min, and 50 mg of Au/AC.

Fig.4 Chemical reaction equation for the oxidation of glucose and the conversion and yield of glucose oxidation to gluconic acid by Au/AC at different reaction temperatures, reaction time, catalyst dosages, and O₂ pressures (general reaction condition: 180 mg of glucose, 25 mL of H₂O). (a) 180 min, 50 mg of Au/AC, and 5 bar O₂; (b) 90 °C, 50 mg of Au/AC, and 5 bar O₂; (c) 90 °C, 180 min, and 5 bar O₂; (d) 90 °C, 180 min, and 50 mg of Au/AC.

Scheme2 Schematic illustration of the continuous flow catalytic reactor system.

Fig.5 Continuous oxidation of xylose (green) and glucose (red) into xylonic and gluconic acid. (a, b) The impact of temperature on the yield of sugar acid. The feeding flow rate was 0.3 mL·min^–1. (c, d) The effect of feeding flow rate on the yield of sugar acid at 80 °C. (e) A plot of WHSV versus the yield of xylonic and gluconic acid. All of the experiments were operated under 80°C , 5 bars of O₂ at 30 mL·min^–1 of flow rate over 150 mg of Au/AC catalyst in the reactor. The sugar concentration of the feeding solution was 2 mg·mL^–1 except for two data points labeled in (e).

Tab.1 The TOF of oxidation of monosaccharide into sugar acid

Tab.2 Kinetic parameters for oxidation of xylose and glucose over Au/AC catalyst

Fig.6 Arrhenius plots for oxidation of (a) xylose (X) and (b) glucose (G) over Au/AC catalyst in flow-through reactors (reaction conditions: 20 mg·mL^–1 of sugar concentration, 1 mL·min^–1 flow rate of the solution over 150 mg of Au/AC at 30?60 °C, 5 bars of O₂ at 30 mL·min^–1 of flow rate).

Fig.7 The thermogravimetric (TG) and TEM images with Au NPs distributions of (a, c) freshly prepared and (b, d) spent for the 5th Au/AC. DTG, derivative thermogravimetric.

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