Hybrid biological and chemocatalytic processes present a unique opportunity to convert biomass into renewable high-value platform chemicals. cis,cis-Muconic acid is a polyunsaturated dicarboxylic acid that can be derived biologically from both sugar and lignin for subsequent catalytic conversion to adipic acid and dimethyl terephthalate. Together, these commodity chemicals are consumed at a rate of over 53 million tonnes per year. However, significant challenges arise when designing stable catalyst materials for continuous processing of bioderived muconic acid, which include active site leaching, organic fouling, and deactivation from biogenic impurities. Therefore, this talk will cover recent efforts to address these issues when upgrading muconic acid to both compounds. For targeting adipic acid, work will be presented to improve hydrogenation catalyst stability against leaching and organic fouling via atomic layer deposition (ALD) with reducible and non-reducible oxide coatings. Findings determined that ALD protective coatings decrease metal leaching by over 5-fold and reduce organic fouling by over 10-fold when compared to carbon-supported catalysts. The economic impact of this technology will be discussed when processing underivatized muconic acid. For targeting dimethyl terephthalate, combined computational and experimental efforts will be highlighted to provide insight into the mechanism of iodine isomerization and catalyst recyclability via downstream crystallization of trans,trans-dimethyl muconate. Lastly, efforts to stabilize heterogeneously supported polyoxometalates will be discussed for muconic acid esterification and Diels-Alder cycloaddition to generate precursors for dimethyl terephthalate production.

Catalytic conversion of bioderived muconic acid to produce adipic acid and dimethyl terephthalate

254th National Meeting (2017)

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