Mechanistic Investigations of Epoxide Aminolysis in Microreactors at High Temperatures and Pressures
Name
NZ MB TFJ KFJ OPRD 2011.pdf
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Author(s)
Zaborenko, Nikolay
Bedore, Matthew W.
Jamison, Timothy F.
Jensen, Klavs F.
Alternative Title
Kinetic and Scale-up Investigations of Epoxide Aminolysis in Microreactors at High Temperatures and Pressures
Date Issued
January 2011
Journal
Organic Process Research & Development
Publisher
American Chemical Society
Citation
Zaborenko, Nikolay et al. “Kinetic and Scale-Up Investigations of Epoxide Aminolysis in Microreactors at High Temperatures and Pressures.” Organic Process Research & Development 15.1 (2011): 131–139. Web.
Version
Author's final manuscript
Abstract
A continuous-flow microreactor is applied for a kinetic study of a model β-amino alcohol
formation by epoxide aminolysis. A large number of experiments are performed in a short time
with minimal reagent consumption. The kinetics of formation of secondary aminolysis between
starting epoxide and product are decoupled from the primary synthesis, constructing a complete
model for desired product formation. The activation energy for the formation of desired product
is observed to be higher than those for regioisomer formation and for secondary aminolysis,
indicating that increasing temperature improves selectivity in addition to accelerating the
reaction. A set of optimized conditions is then selected for best reaction performance, and a
scaled-up process is performed, demonstrating improvement on a meso-scale.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/op100252m
