Synthesis of Dimethyl Carbonate by Transesterification of Methanol with Propylene Carbonate Catalyzed by Choline-Based Amino Acid Ionic Liquids

IF 2.3 4区化学 Q3 CHEMISTRY, PHYSICAL

Catalysis Letters Pub Date : 2025-05-21 DOI:10.1007/s10562-025-05039-z

Hao Liu, Shiyu Liu, Weihua Shen, Yunjin Fang

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Abstract

In this study, we developed a series of choline-based amino acid ionic liquids ([Cho][AA]-ILs) using three alkaline amino acids and choline as environmentally friendly catalysts for synthesizing dimethyl carbonate through transesterification of propylene carbonate with methanol. Through systematic screening, choline arginine ([Cho][Arg]) demonstrated superior catalytic performance and was selected for further optimization. A response surface methodology (RSM) with Box-Behnken design (BBD) was employed to systematically investigate the synergistic effects of key reaction parameters: catalyst concentration (3.6 wt%), reaction time (2.3 h), and temperature (79.4 °C) at a methanol to propylene carbonate molar ratio of 12:1. Under these optimized conditions, the system achieved 71.2% propylene carbonate conversion efficiency under atmospheric reflux. Notably, the catalyst exhibited remarkable recyclability, maintaining approximately 40% conversion efficiency after 12 reaction cycles. Experiments and characterizations revealed that the decomposition of guanidine groups on the arginine side chain caused by high temperature was the main reason for the deactivation of the catalyst. The [Cho][Arg] catalyst distinguishes itself through its facile single-step synthesis, low environmental toxicity, and cost-effective raw materials, demonstrating significant potential for sustainable industrial applications in carbonate ester production.

Graphical Abstract

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胆碱基氨基酸离子液体催化甲醇与碳酸丙酯酯交换合成碳酸二甲酯

本研究以三种碱性氨基酸和胆碱为催化剂，制备了一系列胆碱基氨基酸离子液体（[Cho][AA]-ILs），用于碳酸丙烯与甲醇酯交换合成碳酸二甲酯。通过系统筛选，胆碱精氨酸（[Cho][Arg]）表现出优异的催化性能，并被选中进行进一步优化。采用Box-Behnken设计（BBD）响应面法（RSM）系统考察了甲醇与碳酸丙烯酯摩尔比为12:1时催化剂浓度（3.6 wt%）、反应时间（2.3 h）和温度（79.4°C）等关键反应参数的协同效应。在此优化条件下，常压回流下碳酸丙烯酯转化率达到71.2%。值得注意的是，该催化剂具有显著的可回收性，在12个反应循环后仍保持约40%的转化效率。实验和表征表明，高温引起精氨酸侧链上胍基的分解是催化剂失活的主要原因。[Cho][Arg]催化剂以其简单的单步合成、低环境毒性和低成本的原材料而著称，在碳酸酯生产中显示出巨大的可持续工业应用潜力。图形抽象

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来源期刊

Catalysis Letters 化学-物理化学

CiteScore

5.70

自引率

3.60%

发文量

327

审稿时长

1 months

期刊介绍： Catalysis Letters aim is the rapid publication of outstanding and high-impact original research articles in catalysis. The scope of the journal covers a broad range of topics in all fields of both applied and theoretical catalysis, including heterogeneous, homogeneous and biocatalysis. The high-quality original research articles published in Catalysis Letters are subject to rigorous peer review. Accepted papers are published online first and subsequently in print issues. All contributions must include a graphical abstract. Manuscripts should be written in English and the responsibility lies with the authors to ensure that they are grammatically and linguistically correct. Authors for whom English is not the working language are encouraged to consider using a professional language-editing service before submitting their manuscripts.