[4+4]-Cycloaddition of Isoprene for the Production of High-Performance Bio-Based Jet Fuel.

ABSTRACT: Isoprene was efficiently converted to 1,6-dimethyl-1,5-cyclooctadiene (DMCOD) by selective [4+4]-cycloaddition with a catalyst formed by in situ reduction of [(^MePI)FeCl(μ-Cl)]₂ (^MePI = [2-(2,6-(CH₃)₂-C₆H₃-N=C(CH₃))-C₄H₅N]). DMCOD was isolated in 92% yield, at the preparative scale, with a catalyst loading of 0.025 mol%, and a TON of 3680. Catalytic hydrogenation of DMCOD yielded 1,4-dimethylcyclooctane (DMCO). The cyclic structure and ring strain of DMCO afforded gravimetric and volumetric net heats of combustion 2.4 and 9.2% higher, respectively, than conventional jet fuel. In addition, the presence of methyl branches at two sites resulted in a -20 °C kinematic viscosity of 4.17

SUBMITTER: Rosenkoetter KE 

PROVIDER: S-EPMC8009188 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature