Continuous Hydrogenolysis of N-Diphenylmethyl Groups in a Micropacked-Bed Reactor,Organic Process Research & Development

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Continuous Hydrogenolysis of N-Diphenylmethyl Groups in a Micropacked-Bed Reactor
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-12-17 , DOI: 10.1021/acs.oprd.9b00416
Jiacheng Tu _{1,

2} , Le Sang ₁ , Han Cheng ₁ , Ning Ai ₂ , Jisong Zhang ₁

Affiliation

In recent years, with the advancements in continuous flow technology and the ever-increasing demand for green processes, continuous flow chemistry has become more and more widely adopted in the pharmaceutical industry. In this work, the continuous hydrogenolysis of N-diphenylmethylazetidin-3-ol to 3-azetidinol in micropacked bed reactors was demonstrated. The effects of different catalysts, solvent types, and the additives on the reaction in a micropacked-bed reactor were investigated. The results indicate that the reaction rate per reactor volume is increased by 100 times because of the larger interfacial area and shorter diffusion distance in micropacked reactors. To further study the long-term stability of the reaction system, the flow system was successfully operated for 240 h by adjusting the reaction temperature and liquid flow rate. The reaction kinetics model for the hydrogenation of N-diphenylmethylazetidin-3-ol in methanol was studied after the internal and external diffusion limitations were eliminated. In addition, the type of adsorption of the reactants on the catalyst and the rate-determining step of the reaction were investigated.

中文翻译：

微填充床反应器中N-二苯甲基的连续氢解

近年来，随着连续流技术的进步以及对绿色工艺的不断增长的需求，连续流化学已越来越广泛地应用于制药行业。在这项工作中，氮的连续氢解在微填充床反应器中，证明了-二苯基甲基氮杂环丁烷-3-醇至3-氮杂环丁烷。研究了在微填充床反应器中不同催化剂，溶剂类型和添加剂对反应的影响。结果表明，由于微包装反应器中较大的界面面积和较短的扩散距离，每反应器体积的反应速率提高了100倍。为了进一步研究反应系统的长期稳定性，通过调节反应温度和液体流速，使流动系统成功运行了240小时。N加氢的反应动力学模型在消除内部和外部扩散限制后，研究了甲醇中的-二苯基甲基氮杂环丁烷-3-醇。另外，研究了反应物在催化剂上的吸附类型和反应的速率确定步骤。

更新日期：2019-12-18

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