Singlet oxygen reactions in flow; an example of the ene reaction
Scaling and optimising reactions is an important aspect in chemistry, but is not always an easy feat to achieve. Photochemistry is one such area where optimising reactions can prove more of a challenge. From previous application notes no.41 and 42, it has been shown that a number of photochemical reactions were successfully optimised, showing the versatility of the E-Series, V-3 pump and the UV-150 photochemical reactor by applying photochemistry with a heterogeneous catalyst as a slurry in flow. Another area to investigate to showcase the abilities of the E-Series would be using bi-phasic, gas-liquid reactions in photochemistry. Singlet oxygen reactions would be an ideal candidate here, using photosensitisers to promote ground state triplet oxygen to its excited singlet state.
Abstract
This application note demonstrates the use of singlet oxygen in flow, investigating a range of parameters which can affect the conversion and throughput. This app. note focuses on the ene like reaction of singlet oxygen with citronellol. Subsequent app. notes will focus on other singlet oxygen reactions, including 2+2 and 4+2 cycloadditions. Due to the versatility of the V-3 pump, the reagent solution and gaseous oxygen can be pumped simultaneously through the UV-150 photochemical reactor in a bi-phasic flow. Further, using a variable backpressure regulator allows many reaction parameters to be controlled individually and optimized a huge advantage over traditional batch singlet oxygen reactions in which some reaction parameters are difficult to control.
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