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 photo-catalysts, 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.