A novel thermolytic distillation process was developed to depolymerize polyhydroxybutyrate (PHB) for the selective production of crotonic acid. The conditions adopted (170 °C, 150 mbar) were applied to pure PHB and PHB-enriched bacteria containing 60 and 30% of PHB, giving a recovery of crotonic acid of 92, 78 and 58%, respectively. The high efficiency of the developed process poses the basis for a drop-in production of bio-based crotonic acid, whose versatility as a platform chemical has been investigated through a photochemical approach. The photocatalytic addition (promoted by tetrabutylammonium decatungstate - TBADT) of aliphatic and aromatic aldehydes to crotonic acid took place under solar-simulated light irradiation. TBADT triggered thein situformation of valuable acyl radicals from the corresponding aldehydes, thus inducing the desired hydroacylationviaradical conjugate addition. Notably, the functionalization took place in a satisfactory yield quite independently of the adopted sample of crotonic acid (whether commercial or bio-based).

Bio-based crotonic acid from polyhydroxybutyrate: synthesis and photocatalyzed hydroacylation

Parodi A.;Samori' C.;Torri C.;Galletti P.
2021

Abstract

A novel thermolytic distillation process was developed to depolymerize polyhydroxybutyrate (PHB) for the selective production of crotonic acid. The conditions adopted (170 °C, 150 mbar) were applied to pure PHB and PHB-enriched bacteria containing 60 and 30% of PHB, giving a recovery of crotonic acid of 92, 78 and 58%, respectively. The high efficiency of the developed process poses the basis for a drop-in production of bio-based crotonic acid, whose versatility as a platform chemical has been investigated through a photochemical approach. The photocatalytic addition (promoted by tetrabutylammonium decatungstate - TBADT) of aliphatic and aromatic aldehydes to crotonic acid took place under solar-simulated light irradiation. TBADT triggered thein situformation of valuable acyl radicals from the corresponding aldehydes, thus inducing the desired hydroacylationviaradical conjugate addition. Notably, the functionalization took place in a satisfactory yield quite independently of the adopted sample of crotonic acid (whether commercial or bio-based).
Parodi A.; Jorea A.; Fagnoni M.; Ravelli D.; Samori' C.; Torri C.; Galletti P.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/839635
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