Abstract
The hydrogenation of trans,trans-muconic acid was investigated on a Pt/C 5% (wt) catalyst in a batch slurry reactor at constant hydrogen pressure (4 bar) and temperature (323, 333 and 343 K), with the purpose of developing a kinetic model able to predict conversions and product distributions. A dual-site Langmuir–Hinshelwood–Hougen–Watson (LHHW) model with hydrogen dissociation provided good fitting of the experimental data. The model parameters were regressed by robust numerical methods to overcome the computational challenges of the model parameters’ collinearity. Different reaction mechanisms were tested; the best model involved two subsequent hydrogenation steps. The first step yielded from trans,trans-muconic acid a monounsaturated intermediate (trans-2-hexenedioic acid), which was further hydrogenated to adipic acid in the second step. The intermediate was subjected to an equilibrium isomerization with cis-2-hexenedioic acid. The activation energy values and the rate constants were calculated for the reactions, providing the first reference for trans,trans-muconic acid hydrogenation.
Highlights
Muconic acid (MA) is a bio-derived dicarboxylic acid, which has the potential for becoming a strategic intermediate for the polyamide and polyester industry [1,2,3]
A temperature-dependent dual-site LHHW model was successfully applied to the case of the dissociative hydrogenation of ttMA salts to obtain adipic acid
The hypothesized mechanism involves a two-step reaction with the formation of two intermediates, (2Z)-2-hexenedioic acid and
Summary
Muconic acid (MA) is a bio-derived dicarboxylic acid, which has the potential for becoming a strategic intermediate for the polyamide and polyester industry [1,2,3]. Intensive biotechnological research has identified a number of genetically engineered strains able to produce cis,cis-muconic acid (ccMA) in quantitatively significant amounts from different feedstock [4,5,6]. The feedstock flexibility is relevant as both the cellulosic and lignin fractions of the biomass could be employed as cheap and abundant raw materials, opening the door to second generation biorefinery applications for fully sustainable adipic acid production [11]. The reason for the strong interest toward the efficient production of ccMA and its cis,trans and trans,trans isomers is explained by the versatility of these compounds for the production of strategic bulk chemicals
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