File
Authors
Suganuma, Satoshi Center for Research on Green Sustainable Chemistry Tottori University Researchers DB KAKEN
Otani, Akihiro Center for Research on Green Sustainable Chemistry Tottori University
Joka, Shota Center for Research on Green Sustainable Chemistry Tottori University
Asako, Hiroki Center for Research on Green Sustainable Chemistry Tottori University
Takagi, Rika Center for Research on Green Sustainable Chemistry Tottori University
Tsuji, Etsushi Center for Research on Green Sustainable Chemistry Tottori University Researchers DB KAKEN
Katada, Naonobu Center for Research on Green Sustainable Chemistry Tottori University Researchers DB KAKEN
Keywords
2-pyrrolidone
glutamic acid
hydrogenation
pyroglutamic acid
ruthenium
Abstract
Glutamic acid, an abundant nonessential amino acid, was converted into 2-pyrrolidone in the presence of a supported Ru catalyst under a pressurized hydrogen atmosphere. This reaction pathway proceeded through the dehydration of glutamic acid into pyroglutamic acid, subsequent hydrogenation, and the dehydrogenation–decarbonylation of pyroglutaminol into 2-pyrrolidone. In the conversion of pyroglutaminol, Ru/Al2O3 exhibited notably higher activity than supported Pt, Pd, and Rh catalysts. IR analysis revealed that Ru can hydrogenate the formed CO through dehydrogenation–decarbonylation of hydroxymethyl groups in pyroglutaminol and can also easily desorb CH4 from the active sites on Ru. Furthermore, Ru/Al2O3 showed the highest catalytic activity among the tested catalysts in the conversion of pyroglutamic acid. Consequently, the conversion of glutamic acid produced a high yield of 2-pyrrolidone by using the supported Ru catalyst. This is the first report of this one-pot reaction under mild reaction conditions (433 K, 2 MPa H2)„ which avoids the degradation of unstable amino acids above 473 K.
Publisher
Wiley-VCH Verlag
Content Type
Journal Article
Link
ISSN
18645631
EISSN
1864564X
Journal Title
CHEMSUSCHEM
Volume
12
Issue
7
Start Page
1381
End Page
1389
Published Date
2019-04-05
Publisher-DOI
Text Version
Publisher
Rights
(C) 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
Citation
Suganuma Satoshi, Otani Akihiro, Joka Shota, et al. One-Step Conversion of Glutamic Acid into 2-Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation. CHEMSUSCHEM. 2019. 12(7). 1381-1389. doi:10.1002/cssc.201802980
Department
Faculty of Engineering/Graduate School of Engineering
Language
English
Web of Science Key ut
WOS:000467235500012