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Production of Gasoline Fuel from Alga‐Derived Botryococcene by Hydrogenolysis over Ceria‐Supported Ruthenium Catalyst
Author(s) -
Nakaji Yosuke,
Oya Shinichi,
Watanabe Hideo,
Watanabe Makoto M.,
Nakagawa Yoshinao,
Tamura Masazumi,
Tomishige Keiichi
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700200
Subject(s) - hydrogenolysis , catalysis , chemistry , yield (engineering) , squalane , gasoline , carbon fibers , organic chemistry , ruthenium , inorganic chemistry , materials science , metallurgy , composite number , composite material
Hydrogenolysis of hydrogenated botryococcene (Hy‐Bot) was conducted over various supported Ru catalysts, Ir/SiO 2 , and Pt/SiO 2 –Al 2 O 3 . Ru/CeO 2 with very high dispersion showed the highest yield (70 %) of gasoline‐range (C5–C12) alkanes at 513 K. The main gasoline‐range products were dimethylalkanes. This yield is comparable to or higher than the gasoline yields from botryococcene in the literature, which were obtained at much higher temperature. Ir/SiO 2 also showed a high fuel yield, but the activity was much lower than that with the Ru catalysts. The reaction over Pt/SiO 2 –Al 2 O 3 slowed down before total conversion of Hy‐Bot was achieved. Ru/CeO 2 was stable in the hydrogenolysis of Hy‐Bot without loss of activity and selectivity during reuses. The carbon balance was low for the hydrogenolysis of Hy‐Bot over all catalysts if the main products are heavy hydrocarbons, whereas for the hydrogenolysis of squalane the carbon balance was kept near 100 %. 1 H NMR spectra of the product mixture and thermogravimetric analyses of the product mixture and the recovered catalyst revealed that the formation of aromatic compounds, polymeric products, and coke was negligible for the carbon balance. In a model reaction using substrate compounds with a substructure of Hy‐Bot, only 2,5‐dimethylhexane, which has a C6 chain with two C primary −C tertiary bonds, produced a cyclic product, 1,4‐dimethylcyclohexane, which has a higher boiling point than the substrate. This dehydrocyclization reaction makes the product distribution in the hydrogenolysis of Hy‐Bot more complex.