One-Pot Catalytic Transformation of Dicyclopentadiene to High Energy Density Fuel Exo-tetrahydrotricyclopentadiene
- 356 Downloads
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.
KeywordsHigh energy density fuel Tricyclopentadiene Hydrogenation Isomerization Exo-tetrahydrotricyclopentadiene
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.
- 6.Wang W, Chen JG, Song LP, Liu ZT, Liu ZW, Lv J, Xiao JL, Hao ZP (2013) One-step, continuous-flow, highly catalytic hydrogenation-isomerization of dicyclopentadiene to exo-tetrahydrodicyclopentadiene over Ni-supported catalysts for the production of high-energy-density fuel. Energy Fuels 27:6339–6347CrossRefGoogle Scholar
- 15.Burdette GW, Schneider AI (1983) Exo-terahydrotricyclopentadiene, a high density liquid fuel. U.S. Patent No. 4401837Google Scholar