Investigating the photochemical reaction of an oxazolone derivative under continuous-flow conditions: from analytical monitoring to implementation in an advanced UVC-LED-driven microreactor

IF 2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Flow Chemistry Pub Date : 2023-11-07 DOI:10.1007/s41981-023-00284-y

Gaëlle Lebrun, Marie Schmitt, Michael Oelgemöller, Marc Vedrenne, Jean-François Blanco, Karine Loubière

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Abstract

This study examined the photochemical transformation of an oxazolone derivative in a continuous microreactor irradiated by a UVC LED array (273 nm). The aim of this study was to transfer the reaction protocol originally developed under batch conditions to continuous flow and to further evaluate the scope of this application. A custom-built UVC-LED panel was combined with a microchip, and this microflow system allowed to work under perfectly controlled operating conditions. NMR and LC-MS were used to identify and quantify the main products obtained during the reaction. From this, an HPLC method was developed for imine separation, allowing for an easy and fast monitoring of the reaction progress. Subsequently, the influence of the operating conditions (residence time, photon flux density, temperature) on the selectivity and conversion was investigated to identify the most favorable conditions for a specific product. Temperature did not affect conversion but had an impact on the reaction’s selectivity. The developed UVC-LED-driven continuous-flow microreactor was found to be very efficient since a quantum photon balance ratio of 0.7 was enough to convert all the reactant, while at the same time achieving the maximal yield of the target product. Exhaustive irradiation did not change the molar ratio of each compound present in the reaction medium, thus excluding follow-up photoreactions of the products. This work opens promising perspectives for boosting flow photochemistry in the UV-C domain.

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研究连续流条件下一种恶唑酮衍生物的光化学反应：从分析监测到先进的紫外线-LED 驱动微反应器的实施

本研究考察了一种恶唑酮衍生物在紫外 LED 阵列（273 纳米）照射的连续微反应器中的光化学转化。本研究的目的是将最初在间歇条件下开发的反应方案转移到连续流动条件下，并进一步评估这一应用的范围。定制的紫外线 LED 面板与微芯片相结合，这种微流系统可以在完全受控的操作条件下工作。使用 NMR 和 LC-MS 对反应过程中获得的主要产物进行鉴定和定量。由此，开发出了一种用于亚胺分离的高效液相色谱法，可以方便快捷地监测反应的进展情况。随后，研究了操作条件（停留时间、光子通量密度、温度）对选择性和转化率的影响，以确定对特定产物最有利的条件。温度对转化率没有影响，但对反应的选择性有影响。研究发现，所开发的紫外-LED 驱动连续流微反应器非常高效，因为 0.7 的量子光子平衡比足以转化所有反应物，同时还能获得目标产物的最大产量。完全辐照不会改变反应介质中每种化合物的摩尔比，从而排除了产物的后续光反应。这项工作为促进 UV-C 领域的流动光化学开辟了前景广阔的前景。

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来源期刊

Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

6.40

自引率

3.70%

发文量

审稿时长

>12 weeks

期刊介绍： The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.