Organocatalyzed Synthesis of Oleochemical Carbonates from CO2 and Renewables.

ABSTRACT

Bifunctional phosphorus-based organocatalysts proved to be highly efficient for the atom-economic reaction of CO2 and epoxidized oleochemicals. Notably, those products are obtained from CO2 and renewable feedstocks only. Structure-activity relationships have been deduced from a screening of 22 organocatalysts in a test reaction. Bifunctional catalysts based on a phosphonium salt bearing a simple phenolic moiety proved to be extraordinarily active under comparatively mild and solvent-free reaction conditions. In the presence of the most active organocatalyst 12 oleochemical carbonates were isolated in excellent yields up to 99 %. This organocatalyzed reaction represents an excellent example for the realization of the 12 Principles of Green Chemistry as well as the 12 Principles of CO2 Chemistry.