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Fischer-Helferich glycosidation mechanism of glucose to methyl glycosides over Al-based catalysts in alcoholic media
Yu, Mengting1; Li, Yao2; Zhang, Cheng3; Luo, Huaying3; Ge, Chengsheng1; Chen, Xiaobin1; Fu, Lanlan1; Ju, Zhaoyang1,3; Yao, Xiaoqian2
2022-08-16
Source PublicationRSC ADVANCES
Volume12Issue:36Pages:23416-23426
AbstractThe Fischer-Helferich glycosidation reaction is generally the initial step in the conversion of glucose to levulinate in alcohol media. However, the relevant molecular mechanism catalyzed by Al-based catalysts is still not well understood. In this work, the reaction mechanism of the glycosidation from glucose to methyl glycosides catalyzed by Al3+ coordinated with methanol/methoxyl was investigated through density functional theory (DFT) calculations. The whole reaction process includes ring-opening, addition, and ring-closure events. The addition of methanol to the ring-opening structure of glucose makes the electronegativity of C1 site stronger to proceed with the following ring-closure reaction. Among the 28 kinds of ways of ring-closure reaction, the most preferred way is to close the loop through the six-membered ring (O5-C1) to generate methyl glucoside (MDGP). The rate-determining step is the ring-closure and the Al3+ shows a great catalytic effect which is mainly reflected in coordinating with the solvents to transfer protons. The results would be helpful to understanding the Fischer-Helferich glycosidation mechanism catalyzed by Al-based catalysts and comprehend the conversion of glucose to high value-added chemicals.
DOI10.1039/d2ra03945a
Language英语
WOS KeywordFRUCTOSE ISOMERIZATION ; THEORETICAL INSIGHT ; CONVERSION ; LEVULINATE ; BIOMASS ; LIGNOCELLULOSE ; CHEMISTRY ; CELLULOSE ; ZEOLITES ; SOLVENTS
Funding ProjectNational Natural Science Foundation of China[21908222] ; Key R&D Program of Zhejiang Province[2021C02031] ; Research Fund for the Quzhou University[BSYJ202015] ; Research Fund for the Quzhou University[BSYJ202113]
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
Funding OrganizationNational Natural Science Foundation of China ; Key R&D Program of Zhejiang Province ; Research Fund for the Quzhou University
WOS IDWOS:000841911200001
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/54469
Collection中国科学院过程工程研究所
Corresponding AuthorJu, Zhaoyang; Yao, Xiaoqian
Affiliation1.Quzhou Univ, Coll Chem & Mat Engn, Quzhou 324000, Peoples R China
2.Chinese Acad Sci, CAS Key Lab Green Proc & Engn, Beijing Key Lab Ion Liquids Clean Proc, State Key Lab Multiphase Complex Syst,Inst Proc E, Beijing 100190, Peoples R China
3.Xianhe Co Ltd, Quzhou 324000, Peoples R China
Recommended Citation
GB/T 7714
Yu, Mengting,Li, Yao,Zhang, Cheng,et al. Fischer-Helferich glycosidation mechanism of glucose to methyl glycosides over Al-based catalysts in alcoholic media[J]. RSC ADVANCES,2022,12(36):23416-23426.
APA Yu, Mengting.,Li, Yao.,Zhang, Cheng.,Luo, Huaying.,Ge, Chengsheng.,...&Yao, Xiaoqian.(2022).Fischer-Helferich glycosidation mechanism of glucose to methyl glycosides over Al-based catalysts in alcoholic media.RSC ADVANCES,12(36),23416-23426.
MLA Yu, Mengting,et al."Fischer-Helferich glycosidation mechanism of glucose to methyl glycosides over Al-based catalysts in alcoholic media".RSC ADVANCES 12.36(2022):23416-23426.
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