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Catalytic Synthesis of Distillate-Range Ethers and Olefins from Ethanol through Guerbet Coupling and Etherification

Abstract

Synthesis of distillate-range fuels from biomass-derived alcohols has recently received considerable attention due to projected increases in the demands of these fuels and the extensive commercialization of alcohol production. Here we present a two-stage process by which an alcohol such as ethanol or 1-butanol can be converted with high yields into distillate-range ethers and olefins by combining Guerbet coupling and intermolecular dehydration. The ethers can be used as cetane-improvers in diesel fuel, while the olefins can be hydrogenated and blended with gasoline or oligomerized and hydrogenated to jet-range paraffins. The first stage was executed using calcium hydroxyapatite to produce higher linear and branched alcohols at above 80% selectivity at up to 40% conversion with high stability for over 400h time-on-stream operation. Increasing conversion decreases selectivity, producing predominantly mono-ene and diene byproducts. Etherification conversion was performed using the acidic resin AmberlystTM 70 at around 65% conversion. Linear alcohols were converted at above 90% selectivity while branched alcohols were far more selective to olefins (65-75%). Etherification occurs via two mechanisms: a direct mechanism involving the reaction of two alcohols and an indirect mechanism between an alcohol and equilibrated pool of olefins. Cross-etherification was observed between linear and branched alcohols, improving the selectivity to ethers in conversion of the latter. A mixture of C4+ alcohols produced from ethanol condensation at 40% conversion was effectively utilized in etherification at selectivities comparable to the model mixtures. An overall process is presented for the conversion of ethanol to diesel-range ethers and olefins with yields of approximately 80%.

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Supplementary files

Publication details

The article was accepted on 16 May 2019 and first published on 21 May 2019


Article type: Paper
DOI: 10.1039/C9GC01290G
Green Chem., 2019, Accepted Manuscript

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    Catalytic Synthesis of Distillate-Range Ethers and Olefins from Ethanol through Guerbet Coupling and Etherification

    N. Eagan, B. J. Moore, D. J. McClelland, A. M. Wittrig, E. Canales, M. P. Lanci and G. Huber, Green Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9GC01290G

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