Production of Aviation Fuel Range Quadricyclane with 2,5-Hexanedione

Aviation fuel range C12 high-density quadricyclanes were first produced with 2,5-hexanedione (HD), a hydrogenolysis product of cellulose. First, 3-methylcyclopent-2-en-1-one (MCP) was selectively synthesized from the intramolecular cyclization of 2,5-HD. Under a relatively mild reaction condition, satisfactory carbon yield (97%) of MCP was obtained under the catalysis of Na2CO3. Under ultraviolet irradiation, the MCP dimerized at room temperature without using any photosensitizers or photocatalysts, affording polycyclic C12 diketones. Subsequently, the polycyclic C12 diketones were converted to a mixture of C12 polycycloalkanes with quadricyclanes as the major components under the catalysis of acidic zeolite H–Y and commercial Ru/C. The as-obtained C12 polycycloalkane mixture has a high density of 0.910 g mL–1, high volumetric heat value of 39.3 MJ L–1, and low freezing point of 220 K. As a prospective application, it can be utilized as an additive to enhance the payload and range of aircrafts.