Date: 13 November 2019 | Category: News
Here we present our latest application note: 230% increase in throughput of a photocycloaddition demonstrated by Vapourtec High Power LED.
Photocycloaddition of ethene
The [2+2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction, and has been the focus of a review by Bach et al [1].
It can be particularly useful for the synthesis of highly functionalised cyclobutanes of interest in drug discovery and natural products synthesis [2],[3].
The recent publications [4] reported one of the simplest example, the photocyclization of ethene to maleic anhydride. Noting the practical difficulties associated with this chemistry in batch photochemical reactors, not least of which is maintaining a suitably high concentration of ethane. Vapourtec decided this would be a suitable reaction to demonstrate the newly developed high power led light source.
High power LED light source
Many research groups have shown the ability of LED light sources to efficiently excite a photocatalyst and effect valuable and selective chemical transformations under mild conditions. Researcher Groups led by Prof. Dave MacMillan, Prof. Cory Stephenson, Prof. Michael Oelgemoeller and Prof. Steven Ley have successfully demonstrated the potential to scale up these photocatalysed reactions using continuous flow reactors.
In many of the published continuous flow photochemical reactions throughput has been limited by available photons. To counter this the team at Vapourtec have developed a LED light source as a drop-in replacement for the UV-150 that has more than double the photon output compared with the standard lamp.
230% increase in photochemical throughput
This new application note demonstrates the improvement in throughput that can be achieved using the high power LED module as a direct replacement for a standard Vapourtec LED lamp. Taking the optimised conditions from the Naber paper [4] as a starting point. The throughput of the reaction is compared with standard lamp and with the high power lamp. In this work the only change made was to exchange the 60 watt lamp for a 150 watt high power lamp, the reaction throughput for this valuable 2+2 cycloaddition product was increased from 1.3 grams / hour to 2.8 grams / hour.
To download the application note click here
For more information on the high power LED click here
For more information on the UV-150 photochemical reactor click here
For more information on the E-Series system click here
References
[1] S. Poplata, A. Tröster, Y.-Q. Zou, and T. Bach, “Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions,” Chem. Rev., vol. 116, no. 17, pp. 9748–9815, Sep. 2016.
[2] A. Sergeiko, V. V Poroikov, L. O. Hanus, and V. M. Dembitsky, “Cyclobutane-containing alkaloids: origin, synthesis, and biological activities,” Open Med. Chem. J., vol. 2, pp. 26–37, Apr. 2008.
[3] Vapourtec, “Application Note 59 – Automated photochemical library synthesis.” [Online]. Available: https://www.vapourtec.com/flow-chemistry-resource-centre/application-note-59-automated-photochemical-library-synthesis/
[4] E. B. Corcoran, F. Lévesque, J. P. McMullen, and J. R. Naber, “Studies Toward the Scaling of Gas-Liquid Photocycloadditions,” ChemPhotoChem, vol. 2, no. 10, pp. 931–937, Oct. 201