Enhanced Controllability of Fries Rearrangements Using High-Resolution 3D-Printed Metal Microreactor with Circular Channel

Hyune-Jea Lee; Robert C Roberts; Do Jin Im; Se-Jun Yim; Heejin Kim; Ji Tae Kim; Dong-Pyo Kim

doi:10.1002/smll.201905005

Enhanced Controllability of Fries Rearrangements Using High-Resolution 3D-Printed Metal Microreactor with Circular Channel

Small. 2019 Dec;15(50):e1905005. doi: 10.1002/smll.201905005. Epub 2019 Nov 14.

Authors

Hyune-Jea Lee¹, Robert C Roberts², Do Jin Im³, Se-Jun Yim¹, Heejin Kim⁴, Ji Tae Kim⁵, Dong-Pyo Kim¹

Affiliations

¹ Centre for Intelligent Microprocess of Pharmaceutical Synthesis, Department of Chemical Engineering, POSTECH (Pohang University of Science and Technology), Pohang, 37673, South Korea.
² Department of Electrical and Electronic Engineering, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
³ Department of Chemical Engineering, Pukyong National University, Busan, 48513, South Korea.
⁴ Department of Chemistry, College of Science, Korea University, Seoul, 02841, South Korea.
⁵ Department of Mechanical Engineering, The University of Hong Kong, Pokfulam Road, Hong Kong, China.

PMID: 31729122
DOI: 10.1002/smll.201905005

Abstract

High-resolution 3D-printed stainless steel metal microreactors (3D-PMRs) with different cross-sectional geometry are fabricated to control ultrafast intramolecular rearrangement reactions in a comparative manner. The 3D-PMR with circular channel demonstrates the improved controllability in rapid Fries-type rearrangement reactions, because of the superior mixing efficiency to rectangular cross-section channels (250 µm × 125 µm) which is confirmed based on the computational flow dynamics simulation. Even in case of very rapid intramolecular rearrangement of sterically small acetyl group occurring in 333 µs of reaction time, the desired intermolecular reaction can outpace to the undesired intramolecular rearrangement using 3D-PMR to result in high conversion and yield.

Keywords: 3D print; Fries rearrangement; flow chemistry; microreactors; reactive intermediates.

Publication types

Research Support, Non-U.S. Gov't