CO2 fixation into cyclic carbonates catalyzed by single-site aprotic organocatalysts,Reaction Chemistry & Engineering

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CO2 fixation into cyclic carbonates catalyzed by single-site aprotic organocatalysts
Reaction Chemistry & Engineering ( IF 3.4 ) Pub Date : 2022-05-04 , DOI: 10.1039/d2re00157h
Ala'a F. Eftaiha ₁ , Abdussalam K. Qaroush ₂ , Areej K. Hasan ₂ , Wissam Helal ₂ , Feda'a M. Al-Qaisi ₁

Affiliation

CO₂ fixation is a prominent research theme that attracts the attention of scientists, stakeholders and governmental entities with the aim of ultimately bringing commercial products to the market. Herein, a series of mono-, bi-functional and polymeric imidazolium-based catalysts were synthesized and utilized for the production of cyclic carbonates (CCs) using epoxides and 1 bar of CO₂ under mild reaction conditions. In addition, three onium salts, namely, ammonium, phosphonium, and pyridinium, were synthesized and characterized using ¹H/¹³C nuclear magnetic resonance (NMR) and attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopies, together with thermal gravimetric analysis (TGA), high-resolution mass spectrometry (HRMS) and elemental analysis (EA). All the investigated organocatalysts showed almost quantitative CC conversions, which were isolated from the crude reaction and identified spectroscopically. Density functional theory (DFT) calculations revealed that the aforementioned onium salts followed the same detailed mechanism for the cycloaddition reaction, which started with the electrostatic interaction of the onium centers with the oxygen atom of the epoxide. Even in the case of the imidazolium nucleus, the acidic C2 proton played a marginal role in the epoxide activation than in the ring-opening step.

中文翻译：

单中心非质子有机催化剂催化 CO2 固定成环状碳酸酯

CO ₂固定是一个突出的研究主题，吸引了科学家、利益相关者和政府实体的关注，目的是最终将商业产品推向市场。在此，合成了一系列单、双功能和聚合咪唑基催化剂，并用于在温和反应条件下使用环氧化物和 1 bar CO _{2生产环状碳酸酯 (CCs)。}此外，合成了三种鎓盐，即铵、鏻和吡啶鎓，并使用¹ H/ ^{13对其进行了表征。}C 核磁共振 (NMR) 和衰减全反射傅里叶变换红外 (ATR-FTIR) 光谱，以及热重分析 (TGA)、高分辨率质谱 (HRMS) 和元素分析 (EA)。所有研究的有机催化剂都显示出几乎定量的 CC 转化率，这些转化率从粗反应中分离出来并通过光谱鉴定。密度泛函理论 (DFT) 计算表明，上述鎓盐遵循与环加成反应相同的详细机制，该反应始于鎓中心与环氧化物的氧原子的静电相互作用。即使在咪唑核的情况下，酸性C2质子在环氧化物活化中的作用也比在开环步骤中的作用小。

更新日期：2022-05-04

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