Continuous Flow Epoxidation of Alkenes Using a Homogeneous Manganese Catalyst with Peracetic Acid,Organic Process Research & Development

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Continuous Flow Epoxidation of Alkenes Using a Homogeneous Manganese Catalyst with Peracetic Acid
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-01-14 , DOI: 10.1021/acs.oprd.2c00222
Ailbhe A Ryan _{1,

2,

3} , Seán D Dempsey _{1,

2,

3} , Megan Smyth ₁ , Karen Fahey ₂ , Thomas S Moody _{1,

2} , Scott Wharry ₁ , Paul Dingwall ₃ , David W Rooney ₃ , Jillian M Thompson ₃ , Peter C Knipe ₃ , Mark J Muldoon ₃

Affiliation

Epoxidation of alkenes is a valuable transformation in the synthesis of fine chemicals. Described herein are the design and development of a continuous flow process for carrying out the epoxidation of alkenes with a homogeneous manganese catalyst at metal loadings as low as 0.05 mol%. In this process, peracetic acid is generated in situ and telescoped directly into the epoxidation reaction, thus reducing the risks associated with its handling and storage, which often limit its use at scale. This flow process lessens the safety hazards associated with both the exothermicity of this epoxidation reaction and the use of the highly reactive peracetic acid. Controlling the speciation of manganese/2-picolinic acid mixtures by varying the ligand:manganese ratio was key to the success of the reaction. This continuous flow process offers an inexpensive, sustainable, and scalable route to epoxides.

中文翻译：

使用均相锰催化剂和过乙酸对烯烃进行连续流动环氧化

烯烃的环氧化是精细化学品合成中有价值的转化。本文描述的是连续流动工艺的设计和开发，用于在低至 0.05 mol% 的金属负载下使用均相锰催化剂进行烯烃环氧化。在此过程中，原位生成过乙酸并直接进入环氧化反应，从而降低与其处理和储存相关的风险，这通常限制了其大规模使用。这种流动过程减少了与这种环氧化反应的放热性和使用高反应性过乙酸相关的安全隐患。通过改变配体：锰比例来控制锰/2-吡啶甲酸混合物的形态是反应成功的关键。这种连续流动过程提供了一种廉价、可持续且可扩展的环氧化物途径。

更新日期：2023-01-14

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