HPW/MCM-41 catalytic Simmons-Smith cyclopropanation of olefins for synthesis of high-energy–density fuel

Abstract

Simmons-Smith cyclopropanation commonly promoted by CF3COOH is one important method for transforming olefin into high-energy–density cyclopropyl fuel, but it brings problems such as high cost and harm to environment. In this work, a series of highly active solid acid catalysts HPW/MCM-41 is prepared by impregnation method for the cyclopropanation of dicyclopentadiene. The composition, structural and acidity of catalyst were characterized by TEM, XRD, NH3-TPD, etc. The 5 % HPW/MCM-41 contains more Dawson-type P2W18 (H6P2W18O62) and defective-type P2W21 (H6P2W21O71) that can provide the most abundant acid sites. This catalyst shows the best catalytic activity, the conversion and bicyclic product selectivity for cyclopropanation of dicyclopentadiene are 93.4 % and 55.7 %, respectively, both higher than that of CF3COOH. Moreover, such catalyst shows good catalytic activity for several olefin substrates, and can be recycled in several runs. This work provides a green and efficient catalyst for cyclopropanation reactions for synthesis of high-energy–density fuel, pesticide and medicine.