Journal
CHEMSUSCHEM
Volume 11, Issue 23, Pages 4007-4017Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201801816
Keywords
biomass; C-C coupling; fuels; hydrodeoxygenation; supercritical fluids
Funding
- ExxonMobil
- NSF through the University of Wisconsin Materials Research Science and Engineering Center [DMR-1121288]
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Reaction pathways for the conversion of cellulose into C-2-C-6 monoalcohols by supercritical methanol depolymerization and hydrodeoxygenation (SCM-DHDO) over a CuMgAl oxide catalyst have been elucidated using a range of model compounds. SCM-DHDO of intermediate oxygenates including glycerol, methyl lactate, and 1,2-ethanediol produces similar products as those produced from the SCM-DHDO of cellulose. The pathway to C-2-C-6 monoalcohols occurs through rapid C-C coupling reactions between methanol and diols followed by C-C scission between vicinal alcohol groups to produce two monoalcohols. Methyl-branched monoalcohols are produced through a methyl shift in a secondary diol followed by dehydration. Esters are produced by dehydrogenative coupling between an adsorbed methoxy and a primary alcohol. Both dehydrogenation to a ketone and esterification to a methyl ester are in equilibrium with the corresponding alcohol and were reversible. Dehydration of diols is the slowest observed reaction and not a main pathway to monoalcohols. SCM-DHDO of glucose, dihydroxyacetone, and cellulose all produced similar high molecular weight species indicating that condensation of intermediates can produce undesired side products.
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