Issue 14, 2024

“Metafining” of nerolidol with a Grubbs-Hoveyda catalyst to generate high-performance sustainable aviation fuels

Abstract

trans-Nerolidol was quantitatively converted into a stoichiometric mixture of 2-methyl-cyclopentene-1-ol and 2,6-dimethyl-1,5-heptadiene via ring-closing metathesis with a 2nd generation Grubbs-Hoveyda catalyst at 0.03 mol% loading. The alcohol was then converted into tetrahydrodimethyldicyclopentadiene isomers (THDMDCPD) by dehydration, Diels–Alder cycloaddition, and hydrogenation. In parallel, 2,6-dimethyl-1,5-heptadiene was hydrogenated to generate 2,6-dimethylheptane (DMH). A stoichiometric mixture of THDMDCPD and DMH, designated as F1, exhibited outstanding fuel properties including density, gravimetric heat of combustion, and viscosity measurements that met the requirements for Jet-A. In addition, hydrogenation of 2,6-dimethyl-1,5-heptadiene in the presence of a heterogeneous acid catalyst resulted in partial cyclization followed by hydrogenation to yield a mixture containing 70% 2,6-dimethylheptane and 30% 1,1,3-trimethylcyclohexane (F2). F2 exhibited a gravimetric net heat of combustion of 43.69 MJ kg−1 and a kinematic viscosity of only 1.75 mm2 s−1 at −20 °C. The remarkable fuel properties of F1 and F2 suggest that they have applications as sustainable aviation fuels or blendstocks with conventional jet fuel.

Graphical abstract: “Metafining” of nerolidol with a Grubbs-Hoveyda catalyst to generate high-performance sustainable aviation fuels

Supplementary files

Article information

Article type
Paper
Submitted
11 4 2024
Accepted
04 5 2024
First published
06 5 2024

Sustainable Energy Fuels, 2024,8, 3048-3055

“Metafining” of nerolidol with a Grubbs-Hoveyda catalyst to generate high-performance sustainable aviation fuels

C. L. Keller, C. J. Walkling, D. D. Zhang and B. G. Harvey, Sustainable Energy Fuels, 2024, 8, 3048 DOI: 10.1039/D4SE00487F

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