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5-羟甲基糠醛一锅法还原胺化可持续生产伯呋喃胺的近期催化进展

Recent Catalytic Advances on the Sustainable Production of Primary Furanic Amines from the One-Pot Reductive Amination of 5-Hydroxymethylfurfural.

作者信息

Truong Cong Chien, Mishra Dinesh Kumar, Suh Young-Woong

机构信息

Faculty of Education and Research Promotion, University of Toyama, Toyama, 930-8555, Japan.

Center for Creative Convergence Education, Department of Chemical Engineering, Hanyang University, Seoul, 04763, Republic of Korea.

出版信息

ChemSusChem. 2023 Jan 9;16(1):e202201846. doi: 10.1002/cssc.202201846. Epub 2022 Nov 27.

Abstract

5-Hydroxymethylfurfural (5-HMF) represents a well-known class of lignocellulosic biomass-derived platform molecules. With the presence of many reactive functional groups in the structure, this versatile building block could be valorized into many value-added products. Among well-established catalytic transformations in biorefinery, the reductive amination is of particular interest to provide valuable N-containing compounds. Specifically, the reductive amination of 5-HMF with ammonia (NH ) and molecular hydrogen (H ) offers a straightforward and sustainable access to primary furanic amines [i. e., 5-hydroxymethyl-2-furfuryl amine (HMFA) and 2,5-bis(aminomethyl)furan (BAMF)], which display far-reaching utilities in pharmaceutical, chemical, and polymer industries. In the presence of heterogeneous catalysts contanining monometals (Ni, Co, Ru, Pd, Pt, and Rh) or bimetals (Ni-Cu and Ni-Mn), this elegant pathway enables a high-yielding and chemoselective production of HMFA/BAMF compared to other synthetic routes. This Review aims to present an up-to-date highlight on the supported metal-catalyzed reductive amination of 5-HMF with elaborate studies on the role of metal, solid support, and reaction parameters. Besides, the recyclability/adaptability of catalysts as well as the reaction mechanism are also provided to give valuable insights into this potential 5-HMF valorization strategy.

摘要

5-羟甲基糠醛(5-HMF)是一类著名的木质纤维素生物质衍生平台分子。由于其结构中存在许多反应性官能团,这种多功能的结构单元可以转化为许多高附加值产品。在生物炼制中成熟的催化转化反应中,还原胺化反应对于制备有价值的含氮化合物尤为重要。具体而言,5-HMF与氨(NH₃)和分子氢(H₂)的还原胺化反应为制备伯呋喃胺[即5-羟甲基-2-糠胺(HMFA)和2,5-双(氨甲基)呋喃(BAMF)]提供了一种直接且可持续的方法,这些产物在制药、化工和聚合物工业中具有广泛的用途。在含有单金属(Ni、Co、Ru、Pd、Pt和Rh)或双金属(Ni-Cu和Ni-Mn)的多相催化剂存在下,与其他合成路线相比,这种巧妙的方法能够高产率、化学选择性地生产HMFA/BAMF。本综述旨在对负载型金属催化的5-HMF还原胺化反应进行最新的重点介绍,并对金属、固体载体和反应参数的作用进行详细研究。此外,还介绍了催化剂的可回收性/适应性以及反应机理,以便为这种潜在的5-HMF增值策略提供有价值的见解。

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