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壳聚糖负载离子液体,一种用于简化高效合成羧酸、氨基酸和碳水化合物酯的多面催化剂。

Chitosan supported ionic liquid, a multifaceted catalyst for streamlined and efficient synthesis of carboxylic, amino acid and carbohydrate esters.

作者信息

Kakati Praachi, Awasthi Satish Kumar

机构信息

Department of Chemistry, Chemical Biology Laboratory, University of Delhi Delhi 110007 India

出版信息

RSC Adv. 2024 Nov 11;14(49):36193-36208. doi: 10.1039/d4ra05725b.

Abstract

This work presents a sustainable approach for synthesizing esters from carboxylic acids, amino acids and carbohydrates using a robust and eco-friendly chitosan-incorporated ionic liquid under solvent-free conditions. Ionic liquids with carbon chain lengths ranging from 3 to 8 were integrated into the chitosan molecule, resulting in a heterogeneous catalyst optimized for esterification reactions. Among these, the 6-carbon chain ionic liquid demonstrated superior catalytic activity and substrate tolerance. The catalyst's effectiveness was confirmed using advanced analytical techniques. The acidity of the ionic liquid was assessed by observing the interaction between the synthesized IL6 (1,4-bis(5-carboxypentyl)pyrazine-1,4-diium ([BCPPD][Br])) and -nitroaniline UV-Vis studies. Chitosan-IL6, an ionic liquid supported on chitosan, functions as a heterogeneous catalytic system that can be easily removed from reaction mixtures through simple filtration. It also exhibits excellent reusability, maintaining high catalytic activity and structural integrity over 10 catalytic cycles. Moreover, the methodology was successfully scaled up for the gram-scale synthesis of key compounds such as diisopropyl azodicarboxylate, methyl nicotinate, methyl cysteinate, and glucose pentaacetate, highlighting its practical viability.

摘要

这项工作提出了一种可持续的方法,即在无溶剂条件下,使用一种坚固且环保的壳聚糖负载离子液体,由羧酸、氨基酸和碳水化合物合成酯。碳链长度在3至8之间的离子液体被整合到壳聚糖分子中,从而得到一种针对酯化反应优化的非均相催化剂。其中,具有6个碳链的离子液体表现出卓越的催化活性和底物耐受性。使用先进的分析技术证实了该催化剂的有效性。通过观察合成的IL6(1,4-双(5-羧基戊基)吡嗪-1,4-二铵([BCPPD][Br]))与对硝基苯胺之间的相互作用,通过紫外-可见光谱研究评估了离子液体的酸度。壳聚糖负载的离子液体壳聚糖-IL6作为一种非均相催化体系,可通过简单过滤轻松从反应混合物中除去。它还表现出出色的可重复使用性,在10个催化循环中保持高催化活性和结构完整性。此外,该方法成功地扩大规模用于克级合成关键化合物,如偶氮二羧酸二异丙酯、烟酸甲酯、半胱氨酸甲酯和葡萄糖五乙酸酯,突出了其实际可行性。

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