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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #335897

Research Project: Industrial Monomers and Polymers from Plant Oils

Location: Bio-oils Research

Title: Parameters governing ruthenium sawhorse-based decarboxylation of oleic acid

item Doll, Kenneth - Ken
item Bantchev, Grigor
item Walter, Erin
item Murray, Rex
item Moser, Bryan
item Appell, Michael
item LANSING, JAMES - Oak Ridge National Laboratory

Submitted to: Industrial and Engineering Chemistry Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 1/11/2017
Publication Date: 2/1/2017
Publication URL:
Citation: Doll, K.M., Bantchev, G.B., Walter, E.L., Murray, R.E., Appell, M., Lansing, J.C., Moser, B.R. 2017. Parameters governing ruthenium sawhorse-based decarboxylation of oleic acid. Industrial and Engineering Chemistry Research. 56(4):864-871.

Interpretive Summary: The ability to transform natural oils into items used by industry is a goal of American agriculture, as well as a benefit to American consumers. The plastic materials and machine lubricants that we use every day are almost always made from petroleum. Simple substitution of a natural material does not always work. We are currently working on a process which transforms the natural material into the same building blocks that are made from petroleum. This report is about the improvement of one of those processes, where natural lubricant materials can be made from vegetable oil three times more efficiently than before.

Technical Abstract: Ruthenium-catalyzed decarboxylation of 9-cisoctadecenoic is a path to produce biobased olefins. Here, a mechanistic study of this reaction was undertaken utilizing a closed reaction system and a pressure reactor. The proposed mechanism of an isomerization followed by a decarboxylation reaction was consistent with a mathematical kinetic model. That same model was able to accurately predict CO2 evolution. Additionally, computational chemistry was used to determine that the barrier of the oleic acid decarboxylation reaction is 249 kJ mol-1. Using the new information, the efficacy of the decarboxylation reaction was improved to an overall catalytic efficiency of 850 total turnovers.