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Flash Chemistry Extensively Optimized: High‐Temperature Swern–Moffatt Oxidation in an Automated Microreactor Platform
Author(s) -
Nieuwland Pieter J.,
Koch Kaspar,
van Harskamp Noud,
Wehrens Ron,
van Hest Jan C. M.,
Rutjes Floris P. J. T.
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900705
Subject(s) - swern oxidation , microreactor , millisecond , exothermic reaction , chemistry , flow chemistry , continuous flow , benzaldehyde , nanotechnology , organic chemistry , materials science , catalysis , dimethyl sulfoxide , biochemical engineering , physics , engineering , astronomy
Abstract The generally accepted benefits of small lateral dimensions of microreactors (1 μm to 1 mm) enable a different way of performing synthetic chemistry: Extremely short contact times in the millisecond range can circumvent the need for performing highly exothermic and fast reactions at very low temperatures. In order to fully exploit this technology, such fast processes need to be redesigned and investigated for optimal reaction conditions, which can differ drastically from the ones traditionally applied. In a comprehensive study, we optimized the selective Swern–Moffatt oxidation of benzyl alcohol to benzaldehyde by varying five experimental parameters, including reaction time and temperature. Employing an ultrashort mixing and reaction time of only 32 ms, the optimal temperature was determined to be 70 °C, approximately 150 °C higher than in the conventional batch conditions. This remarkable difference shows both the potency of continuous‐flow chemistry as well as the urgency of a paradigm shift in reaction design for continuous‐flow conditions.