Molecular structure and composition elucidation of an industrial humin and its fractions.

Autor:	Constant S; Inorganic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry and Debye Institute for Nanomaterials Science, Faculty of Science, Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands p.c.a.bruijnincx@uu.nl.; Avantium Renewable Polymers B.V. Zekeringstraat 29 1014 BV Amsterdam The Netherlands., Lancefield CS; Inorganic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry and Debye Institute for Nanomaterials Science, Faculty of Science, Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands p.c.a.bruijnincx@uu.nl., Vogelzang W; Wageningen Food & Biobased Research Bornse Weilanden 9 6708 WG Wageningen The Netherlands daan.vanes@wur.nl., Pazhavelikkakath Purushothaman RK; Wageningen Food & Biobased Research Bornse Weilanden 9 6708 WG Wageningen The Netherlands daan.vanes@wur.nl., Frissen AE; Wageningen Food & Biobased Research Bornse Weilanden 9 6708 WG Wageningen The Netherlands daan.vanes@wur.nl., Houben K; NMR Spectroscopy Research Group, Bijvoet Center for Biomolecular Research, Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands., de Peinder P; VibSpec Haaftenlaan 28 4006 XL Tiel The Netherlands., Baldus M; NMR Spectroscopy Research Group, Bijvoet Center for Biomolecular Research, Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands., Weckhuysen BM; Inorganic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry and Debye Institute for Nanomaterials Science, Faculty of Science, Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands p.c.a.bruijnincx@uu.nl., van Es DS; Wageningen Food & Biobased Research Bornse Weilanden 9 6708 WG Wageningen The Netherlands daan.vanes@wur.nl., Bruijnincx PCA; Inorganic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry and Debye Institute for Nanomaterials Science, Faculty of Science, Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands p.c.a.bruijnincx@uu.nl.; Organic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry, Utrecht University, Faculty of Science Universiteitsweg 99 3584 CG Utrecht The Netherlands.
Jazyk:	angličtina
Zdroj:	Green chemistry : an international journal and green chemistry resource : GC [Green Chem] 2024 Mar 21; Vol. 26 (13), pp. 7739-7751. Date of Electronic Publication: 2024 Mar 21 (Print Publication: 2024).
DOI:	10.1039/d4gc00429a
Abstrakt:	Humins, (side-)products of the acid-catalysed dehydration of carbohydrates, will be produced in substantial quantities with the development of industrial biorefining processes. Most structural knowledge about such humins is based on synthetic model humins prepared at lab-scale from typical carbohydrate(-derived) compounds. Here, we report the first extensive characterisation study of an industrial humin. The soluble humin was generated from pilot plant-scale methanolic cyclodehydration of D-fructose to 5-methoxymethyl-2-furfural (MMF), as part of the Avantium YXY® process to produce FDCA. Purification of the industrial humin followed by fractionation allowed isolation of a water-insoluble, high molecular weight fraction (WIPIH) and a water-soluble, low-to-middle molecular weight soluble fraction (WES). Characterisation by elemental analysis, thermogravimetry, IR and NMR spectroscopy and size exclusion chromatography provided a detailed picture of the humin structure in both fractions. Aided by a comprehensive NMR spectral library of furanic model compounds, we identified the main furanic building blocks and inter-unit linkages and propose a structure for this industrial humin sample. The WIPIH and WES fractions were found to be composed of furanic rings interconnected by short aliphatic chains containing a wide range of functionalities including alcohols, ethers, carboxylic acids, esters, aldehydes and ketones. The low level of crosslinking and high functional group content of the industrial humin differ from the more extensively studied, (highly over-)condensed synthetic model humins, towards which they can be considered intermediates. The structural and compositional insights into the nature of an actual industrial humin open up a broad spectrum of valorisation opportunities. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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