HUSCAP logo Hokkaido Univ. logo

Hokkaido University Collection of Scholarly and Academic Papers >
Institute for Catalysis >
Peer-reviewed Journal Articles, etc >

Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol

This item is licensed under:Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International

Files in This Item:
ADI_Lewis_SI_20201015.pdfSupporting Information588.78 kBPDFView/Open
ADI_Lewis_manuscript_20201016.pdf733.89 kBPDFView/Open
Please use this identifier to cite or link to this item:

Title: Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol
Authors: Sagawa, Takuya Browse this author
Kobayashi, Hirokazu Browse this author →KAKEN DB
Fukuoka, Atsushi Browse this author →KAKEN DB
Keywords: Chitin
Acid-catalyzed dehydration
Lewis acid
Homogeneous catalysis
Issue Date: Dec-2020
Publisher: Elsevier
Journal Title: Molecular Catalysis
Volume: 498
Start Page: 111282
Publisher DOI: 10.1016/j.mcat.2020.111282
Abstract: Chitin is an abundant marine biomass consisting of N-acetylglucosamine (NAG) units. NAG is a source for 2-acetamide-2-deoxyisosorbide (ADI), a condensed five-membered ring compound potentially useful for producing nitrogen-containing polymers. The synthetic route of ADI from NAG consists of hydrogenation of NAG to 2-acetamide-2-deoxysorbitol (ADS) by a supported metal catalyst and subsequent dehydration reaction by a BrOnsted acid catalyst. However, the dehydration step has remained a challenge due to low reactivity of the substrate and low selectivity. Here, we report a combination of BrOnsted acid and Lewis acid catalysts for accelerating the ADS dehydration. The additional use of a catalytic amount of ytterbium triflate in the ADS dehydration by trifluoromethanesulfonic acid catalyst shortens the reaction time by one third and moreover increases the yield of ADI by changing regio-selectivity of the reaction. Mechanistic roles of the ytterbium complex are discussed based on the experimental evidences and density functional theory calculations.
Rights: © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license
Type: article (author version)
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 福岡 淳

Export metadata:

OAI-PMH ( junii2 , jpcoar_1.0 )

MathJax is now OFF:


 - Hokkaido University