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Surface-Immobilized ZnN x Sites as High-Performance Catalysts for Continuous Flow Knoevenagel Condensation in Water.

Nan YangHongyan ZhuXiaoxu SunYuewei WuDe DingYin Chen
Published in: ACS applied materials & interfaces (2023)
By immobilizing the metal complex on the substrate surface, our previous results have demonstrated that heterogeneous catalysts with well-dispersed active MNC (metal-nitrogen-carbon) sites can be prepared in a rational and efficient manner. In this study, we employed agarose aerogel (AA) as the substrate to illustrate a straightforward strategy for immobilizing ZnN x sites on the surface. Under relatively low temperatures, the amine group of the ligand condenses with the surface carbonyl group generated in situ, resulting in the surface immobilized Zn sites. This can be supported by the IR, PXRD, and XPS data. Comprehensive characterization methods, including synchrotron powder XRD and spherical aberration-corrected TEM, confirmed the absence of ZnN x site aggregation in the surface immobilization process, even with a high Zn content (up to 8 wt %). The immobilized ZnN x sites exhibited high catalytic performance in Knoevenagel condensation, and α,β-unsaturated compounds were obtained with high yield in both batch and continuous flow reactions. AA-ZnN x -200 showed the best catalytic activity, which was processed under 200 °C with a Zn content of 4.62 wt %. The immobilized ZnN x sites activated both the aldehyde and nitrile substrates, which were quantitatively converted into the corresponding α,β-unsaturated compounds, with water as the solvent at room temperature. In continuous flow reaction conditions, a conversion rate up to 99% can be achieved with malononitrile. This heterogeneous catalyst can be facilely produced with quantitative yield in a large scale from cheap starting material under mild conditions. No catalyst deactivation was observed after seven batch reaction cycles or 80 h of continuous flow reaction, indicating its high robustness under catalytic reaction conditions. This catalyst enables a separation-free, energy-saving, and environment-friendly production process, offering a practical way for the industrial production.
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