The The Poland Group has been working for years to modify a popular liquid CO2 extraction experiments created for undergraduate laboratories to exhibit the catalytic coupling reaction between dry ice and epoxides under mild conditions. This reaction has been optimized recently to yield 10.4 ± 3.9% conversion to epichlorohydrin carbonate in just 10 minutes utilizing 1 mol% (salen)AlCl and 2 mol% nBu4NBr from epichlorohydrin and dry ice. However, this experiment costs over $6 per pair of students, which is likely prohibitive to smaller laboratories. Herein, we have explored the use of the bimetallic complex [(salen)Al]2O catalyst for this same process. Epichlorohydrin and butylene oxide have been coupled with CO2, yielding higher conversions of their respective cyclic carbonate products at as compared to monometallic (salen)AlCl. Ereduced experimental costs are also reduced to of less than $4 per pair of students despite the added synthetic stepwhen compared to (salen)AlCl/nBu4NBr systems. As with previous successful systems confirmed by the Poland Group, the [(salen)Al]2O/nBu4NBr catalytic system is employable at mild conditions and in inexpensive plastic centrifuge tubes. Chemical conversions can be confirmed by students using 1H NMR spectroscopy. In addition, the [(salen)Al]2O catalyst calls for an air-free synthesis fit for undergraduate Iinorganic Chemistry laboratories, allowing for the implementation of a multiweek experiment designed for students eager to learn challenging synthetic, purification, and characterization techniques.

Undergraduate inorganic laboratory development: Epoxides/CO2 coupling under mild conditions with bimetallic [(salen)Al]2O

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.