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Research Project: New High-Value Biobased Materials with Applications Across Industry

Location: Bio-oils Research

Title: Selective electrochemical oxidation of alcohols catalyzed by partially biobased TEMPO analogs

Author
item Doll, Kenneth - Ken
item Cermak, Steven - Steve

Submitted to: ChemistrySelect
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/28/2022
Publication Date: 8/3/2022
Citation: Doll, K.M., Cermak, S.C. 2022. Selective electrochemical oxidation of alcohols catalyzed by partially biobased TEMPO analogs. ChemistrySelect. 7(29). Article e202201736. https://doi.org/10.1002/slct.202201736.
DOI: https://doi.org/10.1002/slct.202201736

Interpretive Summary: The development of new electrochemically active materials is an important research area vital to the development of the next generation of batteries, fuel cells, and electrochemically active catalysts that are needed for future industry. Inclusion of bio-based materials into these components is currently a very underdeveloped approach. Starting from a medium chain length fatty acid, a new electrochemical catalyst has been produced. It incorporates a chemical structure that has been used in the development of battery cathode materials, but the overall material is ~ 50% comprised of the plant based fatty acid. This new material has been tested in an electrochemical reaction, and gives the same conversion rates as the conventional material. Additionally, the the method is general, and will be suitable for use with a large variety of fatty acids. This research is a starting point, which will benefit those wishing to make electronic materials with a high biobased content, as well as those looking for industrial applications for vegetable oil based products.

Technical Abstract: A new electrochemical catalyst has been synthesized from an analog of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and the medium chain fatty acid, undecenoic acid. The electrochemical properties of the new material are shifted to more positive potential by ~ 170 mV, typical for other substituted TEMPOs. The straightforward reaction gives a catalyst that has been tested in the oxidation of alcohols to aldehydes and ketones and gives reaction rates similar to TEMPOs when considered on a per nitroxyl basis. However, the new system gives an ~ 3-fold higher primary over secondary selectivity. This reaction shows promise as a versatile method in the potential to synthesize rationally designed electroactive materials with a high biobased content.