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One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
Author(s) -
Suganuma Satoshi,
Otani Akihiro,
Joka Shota,
Asako Hiroki,
Takagi Rika,
Tsuji Etsushi,
Katada Naonobu
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201802980
Subject(s) - chemistry , decarbonylation , catalysis , dehydrogenation , glutamic acid , hydrogen , ruthenium , hydroxymethyl , medicinal chemistry , organic chemistry , amino acid , biochemistry
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/Al 2 O 3 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 CH 4 from the active sites on Ru. Furthermore, Ru/Al 2 O 3 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 H 2 )„ which avoids the degradation of unstable amino acids above 473 K.