In recent years, the Poland Group has been developing a laboratory experiment for undergraduate Organic, Inorganic, and/or Green Chemistry students to demonstrate the catalytic coupling of epoxides and carbon dioxide (CO2) to yield value-added cyclic carbonates. In most cases, this process requires the use of high temperatures and/or high pressures of CO2, inherently limiting undergraduate exposure to this exciting chemistry. In our work, a popular liquid CO2 extraction experiment has been modified to perform the CO2/epoxide coupling under relatively mild conditions. The catalytic system selected for use in this laboratory experiment includes zinc octoate, a simple, low-cost, and commercially-available catalyst along with commercially-available nBu4NBr as cocatalyst. The experiment was first prototyped in a Rose-Hulman Organic Chemistry laboratory during Spring Quarter 2019. Utilizing 4 mol% Zn(Oct)2 and 8 mol% nBu4NBr, sophomore-level students reacted butylene oxide and dry ice to yield a 30.7 ± 3.2% conversion to butylene carbonate after just two repeated 10-minute catalytic runs. Students analyzed their data with both FT-IR and 1H NMR, and the necessity of both the catalyst and cocatalyst was displayed using a separate control reaction. This poster will focus on the laboratory experiment’s development, initial execution during Spring 2019, and planned improvements for Spring 2020’s implementation at Rose-Hulman.

Undergraduate laboratory development: Catalytic coupling of epoxides and CO2

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.