764718-04-9Relevant academic research and scientific papers
Ambient Reductive Amination of Levulinic Acid to Pyrrolidones over Pt Nanocatalysts on Porous TiO2 Nanosheets
Xie, Chao,Song, Jinliang,Wu, Haoran,Hu, Yue,Liu, Huizhen,Zhang, Zhanrong,Zhang, Pei,Chen, Bingfeng,Han, Buxing
, p. 4002 - 4009 (2019/03/07)
Construction of N-substituted pyrrolidones from biomass-derived levulinic acid (LA) via reductive amination is a highly attractive route for biomass valorization. However, realizing this transformation using H2 as the hydrogen source under mild conditions is still very challenging. Herein, we designed porous TiO2 nanosheets-supported Pt nanoparticles (Pt/P-TiO2) as the heterogeneous catalyst. The prepared Pt/P-TiO2 was highly efficient for reductive amination of LA to produce various N-substituted pyrrolidones (34 examples) at ambient temperature and H2 pressure. Meanwhile, Pt/P-TiO2 showed good applicability for reductive amination of levulinic esters, 4-acetylbutyric acid, 2-acetylbenzoic acid, and 2-carboxybenzaldehyde. Systematic studies indicated that the strong acidity of P-TiO2 and the lower electron density of the Pt sites as well as the porous structure resulted in the excellent activity of Pt/P-TiO2.
Reductive amination of ethyl levulinate to pyrrolidones over AuPd nanoparticles at ambient hydrogen pressure
Muzzio, Michelle,Yu, Chao,Lin, Honghong,Yom, Typher,Boga, Dilek A.,Xi, Zheng,Li, Na,Yin, Zhouyang,Li, Junrui,Dunn, Joshua A.,Sun, Shouheng
supporting information, p. 1895 - 1899 (2019/04/29)
Herein, we describe a AuPd catalyst for selective and solventless conversion of ethyl levulinate (EL) and amines to pyrrolidones under ambient pressure. The optimized Au66Pd34 nanoparticle catalyst was stable and reusable over 10 runs. AuPd catalysis was extended to reductive amination of levulinic acid and 4-acetylbutyric acid, providing a green chemistry approach under milder conditions not only to pyrrolidones, but also to piperidines, both of which are important scaffolds in designing polymers, natural products and pharmaceuticals.
Chemicals from Biomass: Chemoselective Reductive Amination of Ethyl Levulinate with Amines
Vidal, Juan D.,Climent, Maria J.,Concepcion, Patricia,Corma, Avelino,Iborra, Sara,Sabater, Maria J.
, p. 5812 - 5821 (2015/10/12)
N-substituted-5-methyl-2-piyrrolidones have been obtained by reductive amination of ethyl levulinate with amines in the presence of H2 as reducing agent under solvent-free conditions. The process involves as a first step the formation of an imine intermediate followed by hydrogenation of the imine group and subsequent cyclization into pyrrolidone. Pt/TiO2 with Pt crystal faces decorated with TiOx is a very active and chemoselective catalyst, being possible to achieve high conversion and selectivity to the corresponding N-substituted-5-methyl-2-pyrrolidones even when other groups susceptible of hydrogenation such as vinyl, carbonyl, or cyano groups are present in the amine moiety. A kinetic study showed that the reaction-controlling step is the formation of the imine intermediate. The rate of formation is enhanced by the presence of protonic acid sites generated on the support by hydrogen dissociation on the metal, resulting in a true bifunctional catalyst for the reaction.
Production of 5-mehyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive of levulinic acid esters with aryl and alkyl amines
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Page 11, (2008/06/13)
This invention relates to a process for producing 5-methyl-N-aryl-2-pyrrolidone, 5-methyl-N-alkyl-2-pyrrolidone, and 5-methyl-N-cycloalkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl amines utilizing a metal catalyst, which is optionally supported.
