Parameters Governing Ruthenium Sawhorse-Based Decarboxylation of Oleic Acid

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 CO 2 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.

Comparative Amine‐Catalyzed Thia‐Michael Reactions of Primary and Secondary Thiols with Maleic and Itaconic Anhydrides and Esters

“…In order to gain additional insight into the observed products, DFT was used. Groups, including our own, [21] have utilized DFT to calculate a wide range of properties such as pKa values [22] and dielectric constants [23] . It has even been used for thiol reactions, [24] and for itaconic acid [25] …”

A perspective on catalytic production of olefinic compounds from biomass

“…However, because of the requirement of severe conditions for the decarboxylation, it is difficult to selectively convert an unsaturated fatty acid to the corresponding olen, such as oleic acid to cis-8-heptadecene, without isomerization, cracking or coking. 279,280 Metathesis is a useful reaction for further conversion of the internal olens which will be produced by decarboxylation of unsaturated fatty acids. 281,282…”

A review of thermal homogeneous catalytic deoxygenation reactions for valuable products

“…There were also other reactions such as the decarboxylation, dehydrogenation, isomerization, hydrogenation, and cyclization/aromatization took place, which made a mixture of predominantly alkenes (Knothe et al, 2017). Doll et al (2017) calculated and fitted the activation energy of the oleic acid decarboxylation reaction, which was 249 kJ mol À1 (Knothe et al, 2017).…”