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Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d ‐Proline from Furfural
Author(s) -
Song Song,
Fung Kin Yuen Vincent,
Di Lu,
Sun Qiming,
Zhou Kang,
Yan Ning
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006315
Subject(s) - furfural , biorefinery , chemistry , raw material , yield (engineering) , decarbonylation , reductive amination , catalysis , organic chemistry , materials science , metallurgy
Production of renewable, high‐value N‐containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single‐step conversion of furfural to pyrrole in 75 % yield as a key N‐containing building block, achieved via tandem decarbonylation–amination reactions over tailor‐designed Pd@S‐1 and H‐beta zeolite catalytic system. Pyrrole was further transformed into dl ‐proline in two steps following carboxylation with CO 2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d ‐proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high‐value organonitrogen chemicals through pyrrole as a hub molecule.