589-53-7Relevant articles and documents
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Korobeinikova,S.A. et al.
, (1969)
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Hydrodeoxygenation of the angelica lactone dimer, a cellulose-based feedstock: Simple, high-yield synthesis of branched C7-C10 gasoline-like hydrocarbons
Mascal, Mark,Dutta, Saikat,Gandarias, Inaki
supporting information, p. 1854 - 1857 (2014/03/21)
Dehydration of biomass-derived levulinic acid under solid acid catalysis and treatment of the resulting angelica lactone with catalytic K 2CO3 produces the angelica lactone dimer in excellent yield. This dimer serves as a novel feedstock for hydrodeoxygenation, which proceeds under relatively mild conditions with a combination of oxophilic metal and noble metal catalysts to yield branched C7-C10 hydrocarbons in the gasoline volatility range. Considering that levulinic acid is available in >80 % conversion from raw biomass, a field-to-tank yield of drop-in, cellulosic gasoline of >60 % is possible. Fuel for thought: Biomass-derived levulinic acid can be converted in three simple steps via the angelica lactone dimer into branched, gasoline-range hydrocarbons in high yield by using a combination of oxophilic metal and noble metal catalysts (see scheme). Copyright
Ring opening of decalin via hydrogenolysis on Ir/- and Pt/silica catalysts
Haas, Andreas,Rabl, Sandra,Ferrari, Marco,Calemma, Vincenzo,Weitkamp, Jens
experimental part, p. 97 - 109 (2012/07/13)
The catalytic conversion of cis-decalin was studied at a hydrogen pressure of 5.2 MPa and temperatures of 250-410 °C on iridium and platinum supported on non-acidic silica. The absence of catalytically active Br?nsted acid sites was indicated by both FT-IR spectroscopy with pyridine as a probe and the selectivities in a catalytic test reaction, viz. the hydroconversion of n-octane. On iridium/silica, decalin hydroconversion starts at ca. 250-300 °C, and no skeletal isomerization occurs. The first step is rather hydrogenolytic opening of one six-membered ring to form the direct ring-opening products butylcyclohexane, 1-methyl-2-propylcyclohexane and 1,2- diethylcyclohexane. These show a consecutive hydrogenolysis, either of an endocyclic carboncarbon bond into open-chain decanes or of an exocyclic carboncarbon bond resulting primarily in methane and C9 naphthenes. The latter can undergo a further endocyclic hydrogenolysis leading to open-chain nonanes. All individual C10 and C9 hydrocarbons predicted by this direct ring-opening mechanism were identified in the products generated on the iridium/silica catalysts. The carbon-number distributions of the hydrocracked products C9- show a peculiar shape resembling a hammock and could be readily predicted by simulation of the direct ring-opening mechanism. Platinum on silica was found to require temperatures around 350-400 °C at which relatively large amounts of tetralin and naphthalene are formed. The most abundant primary products on Pt/silica are spiro[4.5]decane and butylcyclohexane which can be readily accounted for by the well known platinum-induced mechanisms described in the literature for smaller model hydrocarbons, namely the bond-shift isomerization mechanism and hydrogenolysis of a secondary-tertiary carboncarbon bond in decalin.
