Experiments and Kinetic Modeling of Fructose Dehydration to 5-Hydroxymethylfurfural with Hydrochloric Acid in Acetone–Water Solvent

Abstract

This work presents experimental and kinetic modeling studies on fructose dehydration to 5-hydroxymethylfurfural (HMF) in the solution of mixed acetone and water, catalyzed by hydrochloric acid (HCl). A reaction scheme that added an intermediate was proposed. A corresponding kinetic model that considered the parameters, including temperature (383−423 K), initial substrate concentration (10−100 g/L), and catalyst concentration (5−60 mmol/L), was established, and the influence of solvent ratio (3−19) was also studied. The maximum yield was 91% in the ideal plug flow reactor under the optimized condition (T = 383 K, C F0 = 10 g/L, C HCl = 10 mmol/L). The model can well support the delicate reactor design since an industrially accessible HMF production process was proposed in this work.

One-Pot Method for the Synthesis of 2,5-Furandicarboxylic Acid from Fructose: In Situ Oxidation of 5-Hydroxymethylfurfural and 5-Acetoxymethylfurfural over Co/Mn/Br Catalysts in Acetic Acid

“…The fructose conversion of 65% was achieved using the mediate strong acid H 3 PO 4 as the catalyst, while fructose conversion of 100% was observed using strong acids H 2 SO 4 and HCl as the catalyst under identical conditions. Therefore, H + from mineral acid ionization is highly efficient for the dehydration of fructose, which has been recognized by many researchers . Additionally, all the hydrohalogen acids including HCl, HBr, and HI showed more excellent catalytic performance on the yield of HMF and AMF than oxyacids, like H 3 PO 4 and H 2 SO 4 , which suggests that halogen ions as the superior nucleophilic reagent play a remarkable role in the conversion of fructose into HMF and AMF.…”

“…Therefore, H + from mineral acid ionization is highly efficient for the dehydration of fructose, which has been recognized by many researchers. 37 Additionally, all the hydrohalogen acids including HCl, HBr, and HI showed more excellent catalytic performance on the yield of HMF and AMF than oxyacids, like H 3 PO 4 and H 2 SO 4 , which suggests that halogen ions as the superior nucleophilic reagent play a remarkable role in the conversion of fructose into HMF and AMF.…”

A Closed-Loop Biorefinery Approach for the Valorization of Winery Waste: The Production of Iron-Sulfonated Magnetic Biochar Catalysts and 5-Hydroxymethyl Furfural from Grape Pomace and Stalks

“…5-HMF can be produced through the dehydration of simple sugars, such as glucose and fructose, in the presence of appropriate homogeneous and heterogenous catalysts. Homogeneous acid catalysts like mineral acids [42], organic acids [43] and ionic liquids [44] present several disadvantages, including low selectivity, corrosion of the equipment, low sustainability, high toxicity and the difficulty in the recovery of the catalyst. To overcome these problems, heterogeneous acid catalysts such as ion-exchange resins [45], metal oxides [46] and heteropoly acids [47] are currently used, because they are less corrosive and easily recoverable at the end of a reaction cycle.…”

A Network of Processes for Biorefining Burdock Seeds and Roots

“…5-HMF is a platform molecule that finds several applications in the synthesis of fine chemicals, polymers, biofuels, and pharmaceuticals [ 59 , 60 ]. Components of cellulose and other polysaccharides such as glucose and fructose can be converted into 5-HMF by dehydration reactions in the presence of homogeneous acid catalysts such as organic acids [ 61 ], ionic liquids [ 62 ], and mineral acids [ 63 ]. However, these processes have several drawbacks in terms of sustainability, including corrosion of the equipment, high toxicity, and recovery of the catalyst.…”