Stoichio-kinetic modeling and optimization of chemical synthesis: Application to the aldolic condensation of furfural on acetone

Abstract

The condensation reaction of furfural (F) on acetone (Ac) gives a high added value product, the 4-(2-furyl)-3-buten-2-one (FAc), used as aroma in alcohol free drinks, ice, candies, gelatines and other products of current life. This synthesis valorises the residues of sugar cane treatment since furfural is obtained by hydrolysis of sugar cane bagasse followed by vapor training extraction. In the face of numerous and complex reactions involved in this synthesis, it is very complicated to define the kinetic laws from exact stoichiometry. A solution allowing to cope the problem consists in identifying an appropriate stoichiometric model. It does not attempt to represent exactly all the reaction mechanisms, but proposes a mathematical support to integrate available knowledge on the transformation. The aim of this work is the determination of stoichiometric and kinetic models of the condensation reaction of furfural on acetone. Concentrations of reagents and products are determined by gas and liquid chromatography. Concentration profiles obtained at different temperatures are used to identify kinetic parameters. The model is then used for the optimization of the production of FAc. The interest of such tool is also shown for the scale up of laboratory reactor to a large scale. The anticipation of the reaction behaviour in large scale is crucial especially when the reactor presents important limitations of thermal exchange capacity.

Base-Catalyzed Reactions in Biomass Conversion: Reaction Mechanisms and Catalyst Deactivation

“…Diacetone alcohol is the main by-product that can be generated in this reaction because the first part of both reactions (acetone self-condensation and furfural-acetone crosscondensation) is common to both reactions and is catalyzed by same type of active site [61]. This mechanism is in good agreement with the mechanism proposed by other researchers for same reaction [126,131] and other aldolizations involving acetone, such as the citral-acetone condensation [43,129] or the condensation of campholenic aldehyde [132]. Computational methods were also used to identify the mechanism [130].…”

Optical properties of modified epoxy resin with various oxime derivatives in the UV‐VIS spectral region

“…On the other hand, 2-furaldoxime has double C¼ ¼N bonds, and therefore a strong absorption peak has been observed nearly at 280 nm due to n -p* transitions in the UV absorption spectrum of S 2 . This value is quite close to the result given by Fakhfakh et al 18 for furfural, as 274 nm.…”

Catalytic Upgrading of 5‐Hydroxymethylfurfural to Drop‐in Biofuels by Solid Base and Bifunctional Metal–Acid Catalysts

“…Furfuralsa re sustainable renewable feedstock for the manufacture of long chain hydrocarbon fuels through sequential aldol condensation, hydrogenation and hydrodeoxygenation (HDO)p athways. [6][7][8][9] However,t his homogeneous base catalysti sc orrosive and promotes cross-and self-condensation reactions. [4] The transformation of low carbon containing molecules into higherc arbon chain precursors for jet fuels involves the formation of new carbon-carbon bonds.…”