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

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

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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.

Original language	English
Article number	1905005
Journal	Small
Volume	15
Issue number	50
DOIs	https://doi.org/10.1002/smll.201905005
Publication status	Published - 2019 Dec 1

Keywords

3D print
Fries rearrangement
flow chemistry
microreactors
reactive intermediates

ASJC Scopus subject areas

Biotechnology
Chemistry(all)
Biomaterials
Materials Science(all)

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10.1002/smll.201905005

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

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",

author = "Lee, {Hyune Jea} and Roberts, {Robert C.} and Im, {Do Jin} and Yim, {Se Jun} and Heejin Kim and Kim, {Ji Tae} and Kim, {Dong Pyo}",

note = "Funding Information: The authors gratefully acknowledge the support from the National Research Foundation (NRF) of Korea grant funded by the Korean government (No. NRF-2017R1A3B1023598). The authors also acknowledge support from 3D Microprint GmbH. Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/smll.201905005",

language = "English",

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AU - Lee, Hyune Jea

AU - Roberts, Robert C.

AU - Im, Do Jin

AU - Yim, Se Jun

AU - Kim, Heejin

AU - Kim, Ji Tae

AU - Kim, Dong Pyo

N1 - Funding Information: The authors gratefully acknowledge the support from the National Research Foundation (NRF) of Korea grant funded by the Korean government (No. NRF-2017R1A3B1023598). The authors also acknowledge support from 3D Microprint GmbH. Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/12/1

Y1 - 2019/12/1

N2 - 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.

AB - 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.

KW - 3D print

KW - Fries rearrangement

KW - flow chemistry

KW - microreactors

KW - reactive intermediates

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SN - 1613-6810

VL - 15

JO - Small

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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