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

CHEMICAL ENGINEERING SCIENCE [2024]
Yakun Liu, Shennan Yang, Chengxiang Shi, Lun Pan, Xiangwen Zhang, Ji-Jun Zou
ABSTRACT

Simmons-Smith cyclopropanation commonly promoted by CF 3 COOH 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, NH 3 -TPD, etc. The 5 % HPW/MCM-41 contains more Dawson-type P 2 W 18 (H 6 P 2 W 18 O 62 ) and defective-type P 2 W 21 (H 6 P 2 W 21 O 71 ) 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 CF 3 COOH. 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.

MATERIALS

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