Topics in Catalysis

, Volume 58, Issue 4–6, pp 350–358 | Cite as

One-Pot Catalytic Transformation of Dicyclopentadiene to High Energy Density Fuel Exo-tetrahydrotricyclopentadiene

Original Paper

Abstract

Energy density of fuel is an important issue for advanced aircrafts and spacecrafts. Exo-tetrahydrotricyclopentadiene (exo-THTCPD) is a promising high-energy density fuel candidate with many desirable properties, including high volumetric energy content (43.2 MJ/L), high density (1.04 g/mL) and low freezing point (<−40 °C). In this work, we demonstrated the first example of one-pot catalytic synthesis of exo-THTCPD directly from dicyclopentadiene (DCPD). The whole procedure was fulfilled in one-pot by three steps. First, tricyclopentadiene (TCPD) was prepared directly from the dissociation–recombination of DCPD at 200 °C. Then the reaction mixture (the majority is TCPD, mixed with small amount of DCPD and tetracyclopentadiene) was saturated using supported noble metal catalysts at 150 °C under 4.0 MPa H2. Finally, the hydrogenated mixture was treated by AlCl3-catalytic isomerization at 15 °C. Like most synthesis processes, fractional distillation was needed to obtain the final product of exo-THTCPD. Compared with previous routes, the new protocol has many advantages such as one-pot, high concentration, less solvents, low catalyst loading, short reaction time, etc, and therefore showed great potential for industrial applications.

Graphical Abstract

Keywords

High energy density fuel Tricyclopentadiene Hydrogenation Isomerization Exo-tetrahydrotricyclopentadiene 

Notes

Acknowledgments

The authors appreciate financial support by the National Natural Science Foundation of China (21202163). The authors gratefully acknowledge Guoliang Xu for fruitful discussion and Ting Lu for experimental assistance.

Supplementary material

11244_2015_376_MOESM1_ESM.docx (337 kb)
Supplementary material 1 (DOCX 337 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.State Key Laboratory of CatalysisDalian Institute of Chemical Physics, Chinese Academy of SciencesDalianChina

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