Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 21, Issue 12, Pages 2012-2017Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.7b00314
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Funding
- University of Liege (Welcome Grant) [WG-13/03]
- Hercules Foundation [AUGE/11/029]
- Research Foundation - Flanders (FWO)
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The 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 gamma-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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