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Modernization of a Photochemical Reaction for the Undergraduate Laboratory: Continuous Flow Photopinacol Coupling

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A continuous flow photopinacol coupling of benzophenone has been developed and implemented in the undergraduate laboratory. This photoreduction was accomplished using 2-propanol as an H atom donor and cosolvent in… Click to show full abstract

A continuous flow photopinacol coupling of benzophenone has been developed and implemented in the undergraduate laboratory. This photoreduction was accomplished using 2-propanol as an H atom donor and cosolvent in the reaction. The simple and inexpensive UV light source and flow reactor design (less than $350/photochemical flow system) provide an operationally accessible experiment. Students successfully compared the efficiencies (percentage conversion) of both flow and batch methods and explored fundamental continuous flow concepts to explain how and why continuous flow can improve the efficiency of a photochemical reaction. The percentage conversions for the flow reactions (average 82%) were more than 8 times higher than the batch reactions, based on irradiation of equal reaction volumes for 10 min.

Keywords: photopinacol coupling; reaction; continuous flow; flow photopinacol; undergraduate laboratory; flow

Journal Title: Journal of Chemical Education
Year Published: 2019

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