Improvement of ruthenium based decarboxylation of carboxylic acids

Authors: Doll, Kenneth - Ken; Walter, Erin; Bantchev, Grigor; Murray, Rex

Submitted to: Gordon Research Conference Proceedings
Publication Type: Abstract Only
Publication Acceptance Date: 5/17/2016
Publication Date: N/A
Citation: N/A

Interpretive Summary:

Technical Abstract: The removal of oxygen atoms from biobased carboxylic acids is an attractive route to provide the drop in replacement feedstocks that industry needs to continue to provide high performance products. Through the use of ruthenium catalysis, an efficient method where this process can be accomplished on unsaturated carboxylic acid, and without co-reactants, is reported. Detailed here is a systematic study to elucidate factors that are limiting the productivity of this process. The newly optimized system is shown to give more than double the total turnovers in a decarboxylation reaction of oleic acid to produce heptadecene. Also shown are the apparent activation energies of the decarboxylation processes of a series of cinnamic acid analogs. Significant rate enhancement was found, for example, by substitution of a methoxy group in position 4 of the substrate.