Biobased Furanics: Kinetic Studies on the Acid Catalyzed Decomposition of 2-Hydroxyacetyl Furan in Water Using Bronsted Acid CatalystsSoetedjo, J. N. M., van de Bovenkamp, H. H., Deuss, P. J. & Heeres, H. J., May-2017, In : ACS Sustainable Chemistry & Engineering . 5, 5, p. 3993-4001 9 p.
Research output: Contribution to journal › Article › Academic › peer-review
Biobased furanics like 5-hydroxymethylfurfural (5-1-IMF) are interesting platform chemicals for the synthesis of biofuel additives and polymer precursors. 5-HMF is typically prepared from C6 ketoses like fructose, psicose, sorbose and tagatose. A known byproduct is 2-hydroxyacetylfuran (2-HAF), particularly when using sorbose and psicose as the reactants. We here report an experimental and kinetic modeling study on the rate of decomposition of 2-HAF in a typical reaction medium for 5-HMF synthesis (water, Bronsted acid), with the incentive to gain insights in the stability of 2-HAF. A total of 12 experiments were performed (batch setup) in water with sulfuric acid as the catalyst (100-170 degrees C, C-H2SO4 ranging between 0.033 and 1.37 M and an initial 2-HAF concentration between 0.04 and 0.26 M). Analysis of the reaction mixtures showed a multitude of products, of which levulinic acid (LA) and formic acid (FA) were the most prominent (Y-max,Y-FA = 24 mol %, Y-max,Y-LA = 10 mol %) when using HCI. In contrast, both LA and FA were formed in minor amounts when using H2SO4 as the catalyst. The decomposition reaction of 2-HAF using sulfuric acid was successfully modeled (R-2 = 0.9957) using a first-order approach in 2-1-IAF and acid. The activation energy was found to be 98.7 ( 2.2) kJ mol(-1).
|Number of pages||9|
|Journal||ACS Sustainable Chemistry & Engineering|
|Publication status||Published - May-2017|
- Platform chemicals, Hydroxyacetylfuran, Kinetic modeling, Acid catalysis, Levulinic acid, Formic acid, LEVULINIC ACID, D-FRUCTOSE, D-GLUCOSE, SUBCRITICAL WATER, HYDROGEN-TRANSFER, HIGH-TEMPERATURE, CONVERSION, ALDOSES, 2-FURALDEHYDE, DEHYDRATION