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Effect of Lewis acid on catalytic dehydration of a chitin-derived sugar alcohol
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| 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 | | 2-Acetamide-2-deoxyisosorbide |
| 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 https://creativecommons.org/licenses/by-nc-nd/4.0/ | | https://creativecommons.org/licenses/by-nc-nd/4.0/ |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/87489 |
| 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)
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Submitter: 福岡 淳
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