Synthesis and properties of high-energy-density hydrocarbons based on 5-vinyl-2-norbornene

Abstract

A norbornane derivative, exo-tetrahydrodicyclopentadiene, is the main component of the high-density liquid fuel called JP-10. In the current communication we describe the preparation of some related norbornane-containing hydrocarbons and their energetic properties. The desired hydrocarbons were readily obtained in high yields using Diels-Alder and/or cyclopropanation reactions from the industrially available 5-vinyl-2-norbornene. As a result, the hydrocarbons containing two norbornane moieties or norbornyl and cyclopropyl groups were prepared. The heats of combustion, densities and freezing points of the prepared norbornane derivatives were evaluated. High densities in the range of 0.856–0.977 g/cm3 and low freezing points (below −60 °C) were found for the obtained hydrocarbons. By altering the structure of such a hydrocarbons, the energy density as high as 41.24 MJ/L was achieved. The energy densities for the hydrocarbons consisting of two norbornane moieties or norbornyl and cyclopropyl fragments were noticeably higher than that of JP-10. Taking into account the low freezing points, high densities and high energy densities, the developed norbornane-type hydrocarbons can be considered as a promising components for high-energy density liquid propellants.