2‐formyl‐5‐(hydroxymethyl)furan (HMF) derivatives as active complexing agent for CO2 insertion reaction

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-03-31 DOI:10.1002/ejoc.202500119

Giulia Fiorani, Nicola Bragato, Mattia Annatelli, Alessandro Bernardi, Marco Bortoluzzi, Roberto Calmanti, Alvise Perosa, Maurizio Selva

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引用次数: 0

Abstract

Renewable‐based furan compounds derived from 2‐formyl‐5‐(hydroxymethyl)furan (5‐HMF) were successfully employed as catalysts to synthesize cyclic organic carbonates through the reaction of carbon dioxide with epoxides. The effects of temperature, reaction time, reagent ratios, and carbon dioxide pressure were optimized before evaluating various bio‐based complexing agents in combination with different alkali metal halide salts. Among them, 2,5‐bis(hydroxymethyl)tetrahydrofuran (BHTHF) showed the highest efficiency as a complexing agent when paired with sodium bromide (NaBr), enabling the production of industrially relevant cyclic carbonates in high yields (12 examples, achieving 94‐99% epoxide conversion and 70‐99% carbonate selectivity) under mild pressure conditions (carbon dioxide pressure of 1‐10 bar, reaction time of 6 hours, and temperature of 120 °C). Additionally, the BHTHF/NaBr catalytic system demonstrated high stability, maintaining its performance over nine consecutive epoxide additions (8 mmol each) without any loss of efficiency.

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2‐甲酰基‐5‐（羟甲基）呋喃（HMF）衍生物作为CO2插入反应的活性络合剂

以2‐甲酰基‐5‐（羟甲基）呋喃（5‐HMF）为原料，制备了可再生基呋喃化合物，并成功地作为催化剂，通过二氧化碳与环氧化物反应合成了环状有机碳酸盐。考察了温度、反应时间、试剂配比、二氧化碳压力等因素对生物基络合剂与碱金属卤化物组合的影响。其中，2,5‐二（羟甲基）四氢呋喃（BHTHF）在与溴化钠（NaBr）配对时表现出最高的络合效率，可以在温和的压力条件下（二氧化碳压力为1‐10 bar，反应时间为6小时，温度为120℃）以高收率（12个例子，实现94‐99%的环氧化物转化率和70‐99%的碳酸盐选择性）生产工业相关的环状碳酸盐。此外，BHTHF/NaBr催化体系表现出很高的稳定性，在连续9次添加环氧化物（每次8 mmol）的情况下保持其性能，没有任何效率损失。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.