Enhanced Cyclopropanation of Norbornene as a High-Energy Fuel by Pd Single-Site Catalysts

The high strain energy of the three-membered ring can increase the combustion calorific value of space fuels. At present, the cyclopropanation of alkenes is the bottleneck to obtain highly-energy three-member-ring fuels. In this article, Pd single-site catalysts (SSCs) were prepared to catalyze the cyclopropanation of norbornene. Pd2+ on the SSCs enhanced the adsorption of CH2N2 through electrostatic interaction, efficiently forming metal carbene. The conversion and selectivity of norbornene cyclopropanation reached 99.9% and 96.9%, which are much higher than those of commercial Pd/C (conversion 42.3%, selectivity 80.8%). In addition, the obtained tricyclooctane shows excellent properties (density 0.93 g/cm3, calorific value 42.75 MJ/kg) to be a promising high-performance rocket fuel. This work provides an efficient method for the synthesis of cyclopropane-based space fuels from alkenes.

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Journal
Industrial & Engineering Chemistry Research
Published
2025-05-26
DOI
https://doi.org/10.1021/acs.iecr.5c01267
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Enhanced Cyclopropanation of Norbornene as a High-Energy Fuel by Pd Single-Site Catalysts

Yingying Cao, Yanqiang Zhang, Xinyue Zhang, Xiaomin Fang et al.
Industrial & Engineering Chemistry Research
Asymmetric Hydrogenation and Catalysis
article

Enhanced Cyclopropanation of Norbornene as a High-Energy Fuel by Pd Single-Site Catalysts

Yingying Cao, Yanqiang Zhang, Xinyue Zhang, Xiaomin Fang, Xin Tan, Yuan Yao
article en

Abstract

The high strain energy of the three-membered ring can increase the combustion calorific value of space fuels. At present, the cyclopropanation of alkenes is the bottleneck to obtain highly-energy three-member-ring fuels. In this article, Pd single-site catalysts (SSCs) were prepared to catalyze the cyclopropanation of norbornene. Pd2+ on the SSCs enhanced the adsorption of CH2N2 through electrostatic interaction, efficiently forming metal carbene. The conversion and selectivity of norbornene cyclopropanation reached 99.9% and 96.9%, which are much higher than those of commercial Pd/C (conversion 42.3%, selectivity 80.8%). In addition, the obtained tricyclooctane shows excellent properties (density 0.93 g/cm3, calorific value 42.75 MJ/kg) to be a promising high-performance rocket fuel. This work provides an efficient method for the synthesis of cyclopropane-based space fuels from alkenes.

Industrial & Engineering Chemistry ResearchVol. 64(22)
Henan University (CN), Chinese Academy of Sciences (CN), Institute of Process Engineering (CN), Chemical Synthesis Lab (SG), Hunan University of Technology (CN)
National Natural Science Foundation of China
Affordable and clean energy
Openalex Percentile: Top 91%
Asymmetric Hydrogenation and Catalysis
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