Direct carbon-carbon coupling of furanics with acetic acid over Bronsted zeolites

Gumidyala, Abhishek; Wang, Bin; Crossley, Steven

doi:10.1126/sciadv.1601072

Direct carbon-carbon coupling of furanics with acetic acid over Bronsted zeolites

Journal Article · Fri Sep 16 00:00:00 EDT 2016 · Science Advances

DOI:https://doi.org/10.1126/sciadv.1601072· OSTI ID:1437643

Gumidyala, Abhishek ^[1]; Wang, Bin ^[2]; Crossley, Steven ^[2]

Univ. of Oklahoma, Norman, OK (United States). School of Chemical, Biological and Materials Engineering; University of Oklahoma
Univ. of Oklahoma, Norman, OK (United States). School of Chemical, Biological and Materials Engineering

Effective carbon-carbon coupling of acetic acid to form larger products while minimizing CO₂ emissions is critical to achieving a step change in efficiency for the production of transportation fuels from sustainable biomass. Here, we report the direct acylation of methylfuran with acetic acid in the presence ofwater, all ofwhich can be readily produced from biomass. This direct coupling limits unwanted polymerization of furanics while producing acetyl methylfuran. Reaction kinetics and density functional theory calculations illustrate that the calculated apparent barrier for the dehydration of the acid to form surface acyl species is similar to the experimentally measured barrier, implying that this step plays a significant role in determining the net reaction rate. Water inhibits the overall rate, but selectivity to acylated products is not affected.We show that furanic species effectively stabilize the charge of the transition state, therefore lowering the overall activation barrier. These results demonstrate a promising new route to C–C bond–forming reactions for the production of higher-value products from biomass.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Oklahoma, Norman, OK (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: EE0006287; SC0004600

OSTI ID:: 1437643

Journal Information:: Science Advances, Journal Name: Science Advances Journal Issue: 9 Vol. 2; ISSN 2375-2548

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

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The Curious Case of Ketene in Zeolite Chemistry and Catalysis Chowdhury, Abhishek Dutta; Gascon, Jorge Angewandte Chemie International Edition, Vol. 57, Issue 46 https://doi.org/10.1002/anie.201808480	journal	November 2018
Visible-light-driven coproduction of diesel precursors and hydrogen from lignocellulose-derived methylfurans Luo, Nengchao; Montini, Tiziano; Zhang, Jian Nature Energy, Vol. 4, Issue 7 https://doi.org/10.1038/s41560-019-0403-5	journal	June 2019

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