Heptadecene isomers were prepared via facile tandem isomerization-decarboxylation of oleic acid using catalytic triruthenium dodecacarbonyl [Ru3(CO)12]. Chromatographic and spectroscopic characterization of the isolated heptadecene mixture indicated that it consisted of 95.6% internal linear isomers and 4.4% aromatics. Diesel fuel properties such as acid value, cold flow, density, derived cetane number, energy content, kinematic viscosity, lubricity, moisture content, oxidative stability, specific gravity, sulfur content, and surface tension were measured and compared against the petrodiesel standards ASTM D975 and EN 590. Also of interest was a comparison of heptadecene properties with conventional ultra-low sulfur (&lt;15 ppm S) diesel (ULSD) fuel and a 5 vol % blend of the heptadecene isomers in ULSD. The heptadecene mixture yielded higher energy content (47.08 MJ/kg) and derived cetane number (86.9), better sulfur content (not detected), but inferior low temperature behavior (cloud point -1 oC), density (791 kg/m3), and oxidative stability (3.4 h; EN 15751) relative to ULSD. All other fuel properties were similar and within the ranges specified in the petrodiesel standards. In conclusion, from oleic acid renewable hydrocarbons were readily prepared, and they yielded fuel properties amenable to their use as an alternative to or blend component for diesel fuel.

Fuel properties of heptadecene isomers prepared via tandem isomerization-decarboxylation of oleic acid

249th National Meeting (2015)

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