Preparation of Furanyl Primary Amines from Biobased Furanyl Derivatives over Heterogeneous Catalysts

化学 还原胺化 胺化 有机化学 糠醛 催化作用 胺气处理 酰胺 呋喃 亲核细胞 功能群 聚合物
作者
Xin Li,Junqi Zhao,Bin Sun,Cong Wang,Xiaoxin Zhang,Xuhong Mu
出处
期刊:ACS Sustainable Chemistry & Engineering [American Chemical Society]
卷期号:11 (51): 17951-17978 被引量:1
标识
DOI:10.1021/acssuschemeng.3c04593
摘要

Primary amine compounds with high nucleophilicity are crucial, high-value chemicals. They can be made by amination of oxygen-containing functional group compounds, such as aldehydes, ketones, and alcohols, or by reduction of nitrogen-containing compounds containing cyano, nitro, amide, and oxime groups. Renewable biomass resources contain a large number of C–O and C═O bonds that can facilitate the conversion of biomass into primary amine compounds. Furanyl derivatives include functional groups such as hydroxyl, carbonyl, and carboxyl groups. Among them, furfural and 5-hydroxymethylfurfural, as important biological platform molecules, could prepare furfuryl alcohol, furoic acid, 2,5-dihydroxymethylfuran, 2,5-diformylfuran, 2,5-furandicarboxylic acid, and other platform compounds and can directly or indirectly synthesize furfurylamine and 2,5-bis (aminomethyl) furan and 2,5-bis(aminomethyl)tetrahydrofuran. The furanyl amines have an aromatic heterocyclic structure and are nitrogen-containing compounds that are highly functional and applicable. Numerous routes exist for the synthesis of furanyl amines, accompanied by side reactions, such as the coupling of primary amine groups and the hydrogenation of furan rings. Therefore, the production of furanyl amines requires the development of catalysts with efficient activity and selectivity. This study reviews heterogeneous catalytic reactions for the amination of various functional groups in compounds. In particular, the catalytic reaction pathways, reaction mechanisms, and structure–function relationships of the corresponding catalysts are discussed, for the amination of biobased furanyl derivatives containing various functional groups. For the purpose of overcoming the most significant obstacles in the amination reaction, a compilation of meticulously crafted catalyst systems with the proper metals and supports has been presented. Finally, a viable route for the industrial preparation of amines from biobased furanyl derivatives and associated heterogeneous catalyst research directions are anticipated.
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