Fischer–Helferich glycosidation mechanism of glucose to methyl glycosides over Al-based catalysts in alcoholic media

Yu, Mengting; Li, Yao; Zhang, Cheng; Luo, Huaying; Ge, Chengsheng; Chen, Xiaobin; Fu, Lanlan; Ju, Zhaoyang; Yao, Xiaoqian

doi:10.1039/d2ra03945a

Cited by 1 publication

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References 56 publications

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“…The appearance of LG, DGP, and LGO indicated that the degradation of glucose might be through glucose dehydration to LG, and LG converted to LGO and DGP 49 . The existence of product 1,1diethoxyethane might be generated by the C‐C bond breakage of EDGP, which was the second main product 50 . However, there were two more products detected in the ethanol/THF system, which were 2‐ethoxytetrahydrofuran (No.2) and furans (No.3).…”

Section: Resultsmentioning

confidence: 99%

“…49 The existence of product 1,1diethoxyethane might be generated by the C-C bond breakage of EDGP, which was the second main product. 50 However, there were two more products detected in the ethanol/THF system, which were 2-ethoxytetrahydrofuran (No.2) and furans (No.3). The peak area percentage of LG and AGF also decreased in the ethanol/THF system as the reaction time increased.…”

Section: No Compoundmentioning

confidence: 99%

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Experimental study combined with density functional theory and molecular dynamics simulation on the mechanism of glucose alcoholysis reaction

Jia

Zhao

Chen

et al. 2023

Asia-Pacific J Chem Eng

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The reaction characteristics and mechanism of carbohydrates is important in exploring and developing suitable technology for biofuels and biochemical production from lignocellulosic biomass. In this study, experiments combined with density functional theory (DFT) calculation and molecular dynamics (MD) simulation were used to investigate the glucose alcoholysis reaction mechanism catalyzed by extremely low concentrated sulfuric acid. The effects of temperature and tetrahydrofuran (THF) on the distribution of the product in the alcoholysis process of high‐concentration glucose were investigated. DFT calculation results showed that the addition of THF in ethanol can decrease the energy barrier of glucose degradation. Meanwhile, the MD simulation indicated that the catalyst tends to localize more around the glucose molecular, which was beneficial to the glucose degradation in ethanol. Combining the experimental and theoretical results, plausible glucose alcoholysis reaction pathways were proposed in this work. It was found that when temperature was lower than 190°C, the three main pathways were glucose conversion into ethyl glucoside (EDGP); glucose conversion into 1,6‐anhydro‐β‐d‐glucopyranose (LG), then further to levoglucosone (LGO), furans, or 1,4:3,6‐dianhydro‐α‐d‐glucopyranose (DGP); and glucose conversion to fructose. However, at higher temperatures (190 and 220°C), the main reaction pathways were, glucose conversion into LG, LGO, and ethyl levulinate (EL); glucose conversion into fructose, 5‐hydroxymethylfurfural (HMF), 5‐ethoxymethylfurfural (EMF), and EL; and glucose conversion into humins. DFT, MD simulation, and experimental results showed that the addition of THF is beneficial for the EDGP formation from high concentration glucose catalyzed by Brønsted acid.

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Section: Resultsmentioning

confidence: 99%

Section: No Compoundmentioning

confidence: 99%

Experimental study combined with density functional theory and molecular dynamics simulation on the mechanism of glucose alcoholysis reaction

Jia

Zhao

Chen

et al. 2023

Asia-Pacific J Chem Eng

View full text Add to dashboard Cite

show abstract

Fischer–Helferich glycosidation mechanism of glucose to methyl glycosides over Al-based catalysts in alcoholic media

Abstract: The reaction mechanism of conversion of glucose to methyl glycosides (MDGP) catalyzed by Al-based catalysts through Fischer–Helferich glycosidation has been probed by DFT calculations.

Cited by 1 publication

References 56 publications

Experimental study combined with density functional theory and molecular dynamics simulation on the mechanism of glucose alcoholysis reaction

Experimental study combined with density functional theory and molecular dynamics simulation on the mechanism of glucose alcoholysis reaction

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