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Issue 12, 2019
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Catalytic synthesis of distillate-range ethers and olefins from ethanol through Guerbet coupling and etherification

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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 400 h time-on-stream operation. Increasing conversion decreases selectivity, producing predominantly mono-ene and diene byproducts. Etherification was performed using the acidic resin Amberlyst™ 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%.

Graphical abstract: Catalytic synthesis of distillate-range ethers and olefins from ethanol through Guerbet coupling and etherification

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Article information


Submitted
18 Apr 2019
Accepted
16 May 2019
First published
21 May 2019

Green Chem., 2019,21, 3300-3318
Article type
Paper

Catalytic synthesis of distillate-range ethers and olefins from ethanol through Guerbet coupling and etherification

N. M. Eagan, B. M. Moore, D. J. McClelland, A. M. Wittrig, E. Canales, M. P. Lanci and G. W. Huber, Green Chem., 2019, 21, 3300
DOI: 10.1039/C9GC01290G

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