Organic Synthesis International: May 2014

Friday, 30 May 2014

Titania-catalysed oxidative dehydrogenation of ethyl lactate: effective yet selective free-radical oxidation

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Titania-catalysed oxidative dehydrogenation of ethyl lactate: effective yet selective free-radical oxidation

http://pubs.rsc.org/en/Content/ArticleLanding/2014/GC/C4GC00191E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Green Chem., 2014, 16,3358-3363
DOI: 10.1039/C4GC00191E, Paper

Open Access

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Enrique V. Ramos-Fernandez, Norbert J. Geels, N. Raveendran Shiju, Gadi Rothenberg
Set them free? Combining a solid catalyst and a solid free-radical scavenger, gives a free-radical oxidation that gives high selectivity even at high concentrations.

We research here the catalytic oxidative dehydrogenation of ethyl lactate, as an alternative route to ethyl pyruvate. Testing various solid catalysts (Fe₂O₃, TiO₂, V₂O₅/MgO–Al₂O₃, ZrO₂, CeO₂ and ZnO), we find that simple and inexpensive TiO₂ efficiently catalyses this reaction under mild conditions. Furthermore, molecular oxygen was used as the terminal oxidant. Importantly, this reaction runs well also using inexpensive commercial solvent mixtures. Both the desired reaction and the by-products formation follow a free-radical mechanism. Remarkably, adding activated carbon, a solid radical scavenger, hardly affects the catalytic activity, but enhances the product selectivity. This is because this solid radical scavenger hampers the formation of undesired products in solution, without suppressing the oxidation at the catalyst surface.