Modifying the Prins-Pinacol Reaction Using Heterogeneous Catalysts
Faculty Mentor Information
Dr. Leslie Nickerson (Mentor), Idaho State University
Abstract
Green chemistry has recently become a more common branch in chemistry and helps to promote the use of more environmentally friendly, safer, sustainable, cost efficient, and effective methods to help benefit the environment and other organizations. Zeolites are excellent acid catalysts and they are non-toxic, reusable, and abundant, allowing them to be used to make the synthesis of various materials more green and environmentally friendly. This project uses zeolites as a greener and safer alternative in place of homogenous Lewis acid catalysts in the Prins-pinacol reaction. Originally discovered by Mousset in 1969 and researched further by Overman, the Prins-pinacol reaction is an excellent way to synthesize substituted tetrahydrofuran rings. Initial reactions using zeolite as a heterogeneous catalyst were carried out using both batch and flow reactors at moderate temperatures and have had percent conversions of up to 95%. Percent conversions were determined and stereochemistry was analyzed using 1H NMR. Further work on the project will include testing additional heterogeneous zeolite catalysts, analyzing the reactions via gas chromatography, continued and improved use of the flow reactor to achieve higher percent conversions, expanding the substrate scope, and identifying the effect heterogeneous catalysts and restricted pore sizes have on the stereochemistry of the products.
Modifying the Prins-Pinacol Reaction Using Heterogeneous Catalysts
Green chemistry has recently become a more common branch in chemistry and helps to promote the use of more environmentally friendly, safer, sustainable, cost efficient, and effective methods to help benefit the environment and other organizations. Zeolites are excellent acid catalysts and they are non-toxic, reusable, and abundant, allowing them to be used to make the synthesis of various materials more green and environmentally friendly. This project uses zeolites as a greener and safer alternative in place of homogenous Lewis acid catalysts in the Prins-pinacol reaction. Originally discovered by Mousset in 1969 and researched further by Overman, the Prins-pinacol reaction is an excellent way to synthesize substituted tetrahydrofuran rings. Initial reactions using zeolite as a heterogeneous catalyst were carried out using both batch and flow reactors at moderate temperatures and have had percent conversions of up to 95%. Percent conversions were determined and stereochemistry was analyzed using 1H NMR. Further work on the project will include testing additional heterogeneous zeolite catalysts, analyzing the reactions via gas chromatography, continued and improved use of the flow reactor to achieve higher percent conversions, expanding the substrate scope, and identifying the effect heterogeneous catalysts and restricted pore sizes have on the stereochemistry of the products.