Molecular structure, morphology and growth mechanisms and rates of 5-hydroxymethyl furfural (HMF) derived humins

Tsilomelekis, George; Orella, Michael J.; Lin, Zhexi; Cheng, Ziwei; Zheng, Weiqing; Nikolakis, Vladimiros; Vlachos, Dionisios G.

doi:10.1039/C5GC01938A

Molecular structure, morphology and growth mechanisms and rates of 5-hydroxymethyl furfural (HMF) derived humins

Journal Article · Tue Nov 17 00:00:00 EST 2015 · Green Chemistry

DOI:https://doi.org/10.1039/C5GC01938A· OSTI ID:1386780

Tsilomelekis, George ^[1]; ^[1]; Lin, Zhexi ^[1]; Cheng, Ziwei ^[1]; Zheng, Weiqing ^[1]; Nikolakis, Vladimiros ^[1]; Vlachos, Dionisios G. ^[1]

Univ. of Delaware, Newark, DE (United States)

We apply ATR-FTIR spectroscopy, Scanning Electron Microscopy (SEM) and Dynamic Light Scattering (DLS) experiments to investigate the molecular structure, morphology and growth mechanism of 5-hydroxymethyl furfural (HMF) derived humins as a function of HMF conversion. Our FTIR data support a reaction pathway in which humins form either through a ring opening mechanism and/or through substitution at the α or β position via nucleophilic attack. The addition of DMSO as a co-solvent leads to significant changes in the FTIR spectra of humins. We find that the nucleophilic attack pathway is suppressed in the presence of DMSO co-solvent and rationalizes the very small humin particles (~100 nm) observed in SEM images contrary to the large particles (with multimodal size distribution and largest particles of up to 3–4 μm) observed in neat water. DLS experiments under several reaction conditions further confirm the particle size distribution observed via SEM. A plausible reaction network for humin formation, which rationalizes qualitatively our experimental results as well as those reported in the literature, is also postulated.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Delaware, Newark, DE (United States)

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

Grant/Contract Number:: SC0001004

OSTI ID:: 1386780

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 7 Vol. 18; ISSN GRCHFJ; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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