Regioselective Epoxide Ring Opening with Alcohols Using Heterogeneous Lewis Acidic Nano-Zeolites*

Epoxides are versatile intermediates that can be ring opened using different nucleophiles to produce a wide variety of valuable chemicals. The key challenge for this reaction is selectivity. The regioselectivity of epoxide ring opening reactions for alcohols is examined using Lewis acidic catalysts. Through comparing catalytic activities, it is found that Sn-Beta is more active than other similar Lewis acidic catalytic materials such as Sn-MFI and Sn-SBA-15. For all materials, high regioselectivity of >99% is obtained when using epichlorohydrin with methanol. With large substrates such as epoxy hexane, diffusion limitations are encountered that can be overcome through creating zeolites with particle sizes less than 100 nm such as nano-Sn-MFI. These materials can be readily recycled while retaining high catalytic activity and selectivity. Hot filtration tests demonstrate that these catalysts are heterogeneous in nature and stable. Larger substrates such as epoxy octane result in diffusion limitations. We demonstrate the use of a new SDA to produce nano-Sn-Beta. This material can catalyze even larger structures. Overall, this demonstrates the importance of tuning material design to create highly active catalytic materials.