op7b00314_si_001.pdf (2.02 MB)
Continuous-Flow Preparation of γ‑Butyrolactone Scaffolds from Renewable Fumaric and Itaconic Acids under Photosensitized Conditions
journal contribution
posted on 2017-11-21, 00:00 authored by Romaric Gérardy, Marc Winter, Clemens R. Horn, Alessandra Vizza, Kristof Van Hecke, Jean-Christophe M. MonbaliuThe method and results
described herein concern the photosensitized
addition of various alcohols to renewable platform fumaric and itaconic
acids under scalable continuous-flow conditions in glass micro- and
mesofluidic reactors. Alcohols were used both as reagents and as solvents,
thus contributing to a reduced environmental footprint. Process parameters
such as the temperature, light intensity, and the nature as well as
amount of the photosensitizer were assessed under microfluidic conditions
and, next, transposed to a lab-scale mesofluidic reactor connected
with an in-line NMR spectrometer for real-time reaction monitoring.
Substituted γ-butyrolactones, including spiro derivatives with
unique structural features, were obtained with quantitative conversion
of the starting materials and in 47–76% isolated yields. The
model photoaddition of isopropanol to fumaric acid was next successfully
transposed in a pilot-scale continuous-flow photoreactor to further
demonstrate scalability.
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Keywords
light intensitylab-scale mesofluidic reactorScaffoldphotosensitizerscalable continuous-flow conditionsreaction monitoringphotosensitized additionconcernconversionmicrofluidic conditionsPhotosensitized ConditionsButyrolactoneContinuous-Flow PreparationItaconic Acidsmethodspiro derivativesmesofluidic reactorsmaterialsolventnaturein-line NMR spectrometerscalabilityplatform fumaricfootprintreagentmodel photoadditionprocess parametersfumaric acidyieldRenewable FumaricSubstituted γ- butyrolactonesitaconic acidspilot-scale continuous-flow photoreactorisopropanol
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