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Continuous ion-exchange resin catalysed esterification of eugenol for the optimized production of eugenyl acetate using a packed bed microreactor

机译:连续离子交换树脂催化丁香酚酯的酯化,以利用填充床微反应器优化乙酸丁烯酯的生产

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摘要

A green scalable flow-synthesis process for the production of eugenyl acetate, an eugenol derivative with potential applications in food and medicinal chemistry, was developed. Through batch experiments, the anion-exchange resin Amberlyst A-21 was recognized as a suitable catalyst for the esterification of eugenol with acetic anhydride. Next, the process was switched from batch-to flow-mode by using a packed-bed microreactor integrated in an instrumental platform that permitted at the same time continuous control of the main process parameters (flow rate, feed mixture composition, temperature) and the on-line HPLC analysis of the reactor effluent. Thanks to this apparatus, a number of experiments with different reaction conditions have been easily performed to evaluate the effects of temperature and reagent molar ratios on eugenyl acetate production. The results have been used to carry out a central composite rotatable experimental design (CCRD) whose derived response surface model (RSM) suggested an optimal temperature and acetic anhydride to eugenol molar ratio of 95 degrees C and 3 : 1, respectively. The goodness of these theoretically deduced parameters has been experimentally confirmed obtaining, with a flow rate of 40 mu L min(-1), a 95% conversion. The Amberlyst A-21 packed-bed microreactor also demonstrated good long-term stability ensuring, under the above optimized conditions, a high and stable conversion (over 93%) for prolonged reaction times.
机译:开发了一种绿色可扩展的流合成工艺,用于生产乙酸丁二烯酯(丁香酚衍生物,在食品和药物化学中具有潜在应用)。通过分批实验,阴离子交换树脂Amberlyst A-21被认为是丁香酚与乙酸酐酯化的合适催化剂。接下来,通过使用集成在仪器平台中的填充床微反应器,将过程从批处理模式切换为流模式,该平台可同时连续控制主要过程参数(流速,进料混合物组成,温度)和反应器流出物的在线HPLC分析。由于使用了这种装置,可以轻松地进行许多具有不同反应条件的实验,以评估温度和试剂摩尔比对乙酸丁二烯酯生产的影响。该结果已用于进行中央复合可旋转实验设计(CCRD),其衍生的响应表面模型(RSM)建议最佳温度和乙酸酐与丁子香酚的摩尔比分别为95摄氏度和3:1。这些理论推导的参数的优良性已​​通过实验得到证实,流速为40μL min(-1)时,转化率为95%。 Amberlyst A-21填充床微反应器还显示出良好的长期稳定性,从而在上述优化条件下确保了高且稳定的转化率(超过93%),从而延长了反应时间。

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