Catalytic Production of Alanine from Waste Glycerol

• Published in: Angewandte Chemie International Edition Vol. 59; no. 6; pp. 2289 - 2293
• Main Authors: Wang, Yunzhu, Furukawa, Shinya, Song, Song, He, Qian, Asakura, Hiroyuki, Yan, Ning
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 03.02.2020
• Edition: International ed. in English
• Subjects: Absorption spectroscopy; Alanine; Alanine - biosynthesis; Amino acids; Ammonia - chemistry; Bimetals; Biodiesel fuels; Biofuels; biomass; Catalysis; Catalysts; Catalytic converters; Chemical synthesis; Coordination Complexes - chemistry; Density Functional Theory; Glycerol; Glycerol - chemistry; Glycerol - metabolism; heterogeneous catalysis; Hydrogen bonds; Lactic acid; Lactic Acid - chemistry; Nickel - chemistry; Organic chemistry; Pyruvic acid; Raw materials; Ruthenium - chemistry; Scanning transmission electron microscopy; Substrates; surface chemistry; Transmission electron microscopy; X-Ray Absorption Spectroscopy; biomass; surface chemistry; heterogeneous catalysis; glycerol; amino acids
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201912580

Chemical synthesis of amino acids directly from biomass feedstock is rare. Reported here is a one‐step protocol to convert crude glycerol, from the biodiesel industry, into 43 % alanine over a Ru1Ni7/MgO catalyst. The multifunctional catalytic system promotes glycerol conversion into lactic acid, and then into alanine. X‐ray absorption spectroscopy and scanning transmission electron microscopy revealed the existence of bimetallic RuNi species, whereas density‐functional theory calculations suggested Ni‐doped Ru substantially decreased the Ea of C−H bond dissociation of lactate alkoxide to form pyruvate, which is the rate‐determining step. The catalytic route established in this work creates new opportunities for glycerol utilization and enriches the substrate scope of renewable feedstock to access value‐added amino acids. Direct conversion: 43 % alanine was achieved from crude glycerol over a Ru1Ni7/MgO catalyst. Ni‐doped Ru remarkably promoted lactic acid amination, a key step in the reaction. The catalytic route creates new opportunities for glycerol utilization and enriches the substrate scope of renewable feedstock to access value‐added amino acids.