Scale-Up of production of 5-hydroxymethylfurfural-rich adhesive precursors and structural features of humin side products

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Abstract

A batch reaction system (volume 1 L) for scaled-up production of 5-HMF-based adhesive precursor solutions from industrially available fructose syrup was developed. The stabilizing effect of sodium dithionite addition was demonstrated. With this system, no concentration steps are needed in the production of adhesive precursors for wood composite board production. The reaction system was optimized in a design of experiment approach to achieve good reaction conditions and to produce reaction solutions with 5-HMF concentrations appropriate for adhesive synthesis. Only three runs in the adjusted system are required to produce enough precursor for the synthesis of 10 kg of adhesive, thereby enabling the testing of the adhesive systems in particle board trials.

Furthermore, the structure of humin side products from different reaction stages, formed from 5-HMF and byproducts by condensation, aldol-like reactions and attack on furan ring systems, was investigated. The data were compared to information from literature and possible elements of humin structures are proposed.

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Most cited references 26

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Hydroxymethylfurfural, a versatile platform chemical made from renewable resources.

Robert-Jan van Putten, Jan C. van der Waal, Ed de Jong … (2013)

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Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Marina N Matos, Carmen S. R. Freire, Gert-Jan Gruter … (2015)

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Formation, molecular structure, and morphology of humins in biomass conversion: influence of feedstock and processing conditions.

Pieter Bruijnincx, Bert M. Weckhuysen, Hero J Heeres … (2013)

Neither the routes through which humin byproducts are formed, nor their molecular structure have yet been unequivocally established. A better understanding of the formation and physicochemical properties of humins, however, would aid in making biomass conversion processes more efficient. Here, an extensive multiple-technique-based study of the formation, molecular structure, and morphology of humins is presented as a function of sugar feed, the presence of additives (e.g., 1,2,4-trihydroxybenzene), and the applied processing conditions. Elemental analyses indicate that humins are formed through a dehydration pathway, with humin formation and levulinic acid yields strongly depending on the processing parameters. The addition of implied intermediates to the feedstocks showed that furan and phenol compounds formed during the acid-catalyzed dehydration of sugars are indeed included in the humin structure. IR spectra, sheared sum projections of solid-state 2DPASS (13) C NMR spectra, and pyrolysis GC-MS data indicate that humins consist of a furan-rich polymer network containing different oxygen functional groups. The structure is furthermore found to strongly depend on the type of feedstock. A model for the molecular structure of humins is proposed based on the data presented.