[4 + 4]-cycloaddition of isoprene for the production of high-performance bio-based jet fuel

Kyle E. Rosenkoetter, C. Rose Kennedy, Paul J. Chirik, Benjamin G. Harvey

Research output: Contribution to journalArticle

1 Scopus citations

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-NC(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 mm2 s-1, 48% lower than the maximum allowed value for conventional jet fuel. The ability to derive isoprene and related alcohols readily from abundant biomass sources, coupled with the highly efficient [Fe]-catalyzed [4 + 4]-cycloaddition described herein, suggests that this process holds great promise for the economical production of high-performance, bio-based jet fuel blendstocks.

Original languageEnglish (US)
Pages (from-to)5616-5623
Number of pages8
JournalGreen Chemistry
Volume21
Issue number20
DOIs
StatePublished - Jan 1 2019

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

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