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Chemoselective Hydrogenation of Ring‐Strained Monoterpenes: A Route to High‐Performance Sustainable Aviation Fuels
Author(s) -
Woodroffe Josanne-Dee,
Harvey Benjamin G.
Publication year - 2021
Publication title -
energy technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.91
H-Index - 44
eISSN - 2194-4296
pISSN - 2194-4288
DOI - 10.1002/ente.202100221
Subject(s) - jet fuel , sabinene , yield (engineering) , monoterpene , combustion , chemistry , organic chemistry , materials science , chemical engineering , limonene , composite material , essential oil , chromatography , engineering
Sabinene and 3‐carene, bio‐based monoterpene precursors to high‐performance jet fuels, are chemoselectively hydrogenated with reduced PtO 2 at low temperatures (263–298 K), to yield products in which the alkene groups are saturated, whereas cyclopropane rings from the parent hydrocarbons are conserved. Sabinene is selectively converted to a 79:21 mixture of cis:trans‐thujane (1), whereas 3‐carene is converted to a 72:28 mixture of cis:trans‐carane (3). For comparison, the fully hydrogenated species tetrahydrosabinene (2) and 1,1,4‐trimethylcycloheptane ( 4 ) are prepared by hydrogenation with Pd/C. To evaluate 1−4 as advanced jet fuel blendstocks, several key fuel properties are measured. Compared with conventional jet fuel, the hydrogenated monoterpenes exhibit up to 8.6% higher density, 1.3% higher gravimetric net heat of combustion (NHOC), 9.7% higher volumetric NHOC, and 64% lower kinematic viscosity at −20 °C. These properties suggest that 1−4 are valuable blendstocks for conventional jet fuel or sustainable aviation fuel, providing enhanced operability and performance.