Renewal in the world production of plastics with growing amounts of building blocks from biomass is a pressing demand among society. Adipic acid is one of the monomers of nylon 6,6, and, traditionally, is obtained from fossil sources, but it is possible to reduce the muconic acids, deriving it from biomass, to obtain adipic acid. However, these catalyzed reactions use commonly hazardous conditions or reagents; in this study, a pathway to obtain a bio-adipic acid, following the Green Chemistry, is reported. Metal nanoparticles (M NPs; M = Pd, Pt, Ru, Rh) were synthesized in water at 80 °C using sodium lignosulphonate as a reducing and stabilizing agent. They were characterized by TEM and XRD techniques: Pd NPs were larger (21 nm) and spherical in shape; Pt NPs were irregular; Ru and Rh NPs were smallest (1.9 and 5.3 nm, respectively). M NPs were tested as catalyst in the hydrogenation reactions of dicarboxylic acids (fumaric, malonic, trans,trans- and cis,cis-muconic acids) in water at room pressure and temperature. The NPs transformed selectively fumaric and malonic acids to succinic acid, although with different yields. Ru and Pt NPs were moderately active while with Pd NPs, 80% of succinic acid was obtained and with Rh NPs, 100% was observed. Carrying out the hydrogenations on muconic acids at pH 5, the formation of adipic acid was observed with all NPs but selectivities in the presence of Ru, Pt and Pd NPs were not excellent. The selectivity with Rh NPs was remarkable (86% from cis,cis- and about 100% from trans,trans-muconic acid) considering the mild conditions; furthermore, it is attractive that the adipic acid was obtained also from the cis,cis isomer which can be produced from biomass.

The role of Nanoparticle Catalysis in the Nylon Production

Tonucci, Lucia
;
Mascitti, Andrea;Coccia, Francesca;d’Alessandro, Nicola
2022

Abstract

Renewal in the world production of plastics with growing amounts of building blocks from biomass is a pressing demand among society. Adipic acid is one of the monomers of nylon 6,6, and, traditionally, is obtained from fossil sources, but it is possible to reduce the muconic acids, deriving it from biomass, to obtain adipic acid. However, these catalyzed reactions use commonly hazardous conditions or reagents; in this study, a pathway to obtain a bio-adipic acid, following the Green Chemistry, is reported. Metal nanoparticles (M NPs; M = Pd, Pt, Ru, Rh) were synthesized in water at 80 °C using sodium lignosulphonate as a reducing and stabilizing agent. They were characterized by TEM and XRD techniques: Pd NPs were larger (21 nm) and spherical in shape; Pt NPs were irregular; Ru and Rh NPs were smallest (1.9 and 5.3 nm, respectively). M NPs were tested as catalyst in the hydrogenation reactions of dicarboxylic acids (fumaric, malonic, trans,trans- and cis,cis-muconic acids) in water at room pressure and temperature. The NPs transformed selectively fumaric and malonic acids to succinic acid, although with different yields. Ru and Pt NPs were moderately active while with Pd NPs, 80% of succinic acid was obtained and with Rh NPs, 100% was observed. Carrying out the hydrogenations on muconic acids at pH 5, the formation of adipic acid was observed with all NPs but selectivities in the presence of Ru, Pt and Pd NPs were not excellent. The selectivity with Rh NPs was remarkable (86% from cis,cis- and about 100% from trans,trans-muconic acid) considering the mild conditions; furthermore, it is attractive that the adipic acid was obtained also from the cis,cis isomer which can be produced from biomass.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11564/790371
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