Inhibition of Xylene Isomerization in the Production of Renewable Aromatic Chemicals from Biomass-Derived Furans

Williams, C. Luke; Vinter, Katherine P.; Patet, Ryan E.; Chang, Chun-Chih; Nikbin, Nima; Feng, Shuting; Wiatrowski, Matthew R.; Caratzoulas, Stavros; Fan, Wei; Vlachos, Dionisios G.; Dauenhauer, Paul J.

doi:10.1021/acscatal.5b02329

Inhibition of Xylene Isomerization in the Production of Renewable Aromatic Chemicals from Biomass-Derived Furans

Journal Article · Tue Feb 02 23:00:00 EST 2016 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.5b02329· OSTI ID:1865830

Williams, C. Luke ^[1]; Vinter, Katherine P. ^[2]; Patet, Ryan E. ^[3]; Chang, Chun-Chih ^[4]; Nikbin, Nima ^[3]; Feng, Shuting ^[3]; Wiatrowski, Matthew R. ^[3]; Caratzoulas, Stavros ^[3]; Fan, Wei ^[4]; Vlachos, Dionisios G. ^[3]; Dauenhauer, Paul J. ^[5]

Univ. of Massachusetts, Amherst, MA (United States); University of Minnesota
Univ. of Minnesota, Minneapolis, MN (United States)
Univ. of Delaware, Newark, DE (United States)
Univ. of Massachusetts, Amherst, MA (United States)
Univ. of Massachusetts, Amherst, MA (United States); Univ. of Minnesota, Minneapolis, MN (United States)

Here, inhibition of p-xylene isomerization in the presence of H-Y (Si/Al 2.6) and H-BEA (Si/Al 12.5) zeolites was studied under conditions relevant to p-xylene production from 2,5-dimethylfuran (DMF) and ethylene. Through examination of the reaction components, it was shown that both DMF and 2,5-hexanedione inhibit transalkylation and methyl shift reactions of p-xylene, while other reaction components, water and ethylene, do not. Retention of Brønsted acid sites after the reaction was shown through the use of ²⁷Al NMR for both H-Y and H-BEA zeolites, but with a reduction in the ratio of tetrahedrally coordinated aluminum (strong acid sites) to octahedrally coordinated aluminum (Lewis acid sites) coinciding with the disappearance of the framework aluminum. Diffuse reflectance spectroscopy has shown preferential adsorption of DMF and 2,5-hexanedione (DMF + H₂O) relative to p-xylene to the Brønsted acid sites located in the super and sodalite cages of the H-Y. Desorption characteristics for DMF and p-xylene in H-Y and H-BEA were determined by thermogravimetric analysis, consistent with adsorption energetics of individual chemical species and dimeric complexes evaluated by an ONIOM method. Evaluation of three mechanisms, allowing for production of p-xylene from DMF and ethylene while also inhibiting p-xylene isomerization, supports high surface coverage of the active site with 2,5-hexanedione, supported by electronic structure calculations.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Minnesota, Minneapolis, MN (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation; Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001004; AC02-05CH11231

OSTI ID:: 1865830

Alternate ID(s):: OSTI ID: 1387604

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 3 Vol. 6; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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