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 Dzi 2024
Accepted
04 Mud 2024
First published
06 Mud 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements