Continuous flow epoxidation of alkenes using a homogeneous manganese catalyst with peracetic acid

Ailbhe A. Ryan, Seán D. Dempsey, Megan Smyth, Karen Fahey, Thomas S. Moody, Scott Wharry, Paul Dingwall, David W. Rooney, Jillian M. Thompson*, Peter C. Knipe*, Mark J. Muldoon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)
61 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)262-268
Number of pages7
JournalOrganic Process Research & Development
Volume27
Issue number2
Early online date14 Jan 2023
DOIs
Publication statusPublished - 17 Feb 2023

Keywords

  • catalysis
  • continuous processing
  • epoxidation
  • flow chemistry
  • manganese
  • oxidation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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