Tandem Lewis/Brønsted homogeneous acid catalysis: conversion of glucose to 5-hydoxymethylfurfural in an aqueous chromium(iii) chloride and hydrochloric acid solution

Swift, T. Dallas; Nguyen, Hannah; Anderko, Andrzej; Nikolakis, Vladimiros; Vlachos, Dionisios G.

doi:10.1039/c5gc01257k

Tandem Lewis/Brønsted homogeneous acid catalysis: conversion of glucose to 5-hydoxymethylfurfural in an aqueous chromium(iii) chloride and hydrochloric acid solution

Journal Article · Sat Jul 25 00:00:00 EDT 2015 · Green Chemistry

DOI:https://doi.org/10.1039/c5gc01257k· OSTI ID:1370906

Swift, T. Dallas ^[1]; Nguyen, Hannah ^[1]; Anderko, Andrzej ^[2]; Nikolakis, Vladimiros ^[1]; Vlachos, Dionisios G. ^[1]

Univ. of Delaware, Newark, DE (United States)
OLI Systems Inc., Cedar Knolls, NJ (United States)

Here, a kinetic model for the tandem conversion of glucose to 5-hydroxymethylfurfural (HMF) through fructose in aqueous CrCl₃–HCl solution was developed by analyzing experimental data. We show that the coupling of Lewis and Brønsted acids in a single pot overcomes equilibrium limitations of the glucose–fructose isomerization leading to high glucose conversions and identify conditions that maximize HMF yield. Adjusting the HCl/CrCl₃ concentration has a more pronounced effect on HMF yield at constant glucose conversion than that of temperature or CrCl₃ concentration. This is attributed to the interactions between HCl and CrCl₃ speciation in solution that leads to HMF yield being maximized at moderate HCl concentrations for each CrCl₃ concentration. This volcano-like behavior is accompanied with a change in the rate-limiting step from fructose dehydration to glucose isomerization as the concentration of the Brønsted acid increases. The maximum HMF yield in a single aqueous phase is only modest and appears independent of catalysts’ concentrations as long as they are appropriately balanced. However, it can be further maximized in a biphasic system. Our findings are consistent with recent studies in other tandem reactions catalyzed by different catalysts.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC), Washington, D.C. (United States). Catalysis Center for Energy Innovation (CCEI)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0001004

OSTI ID:: 1370906

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 10 Vol. 17; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Tandem Lewis/Brønsted homogeneous acid catalysis: conversion of glucose to 5-hydoxymethylfurfural in an aqueous chromium(iii) chloride and hydrochloric acid solution

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