Curcumin (CM) is a natural polyphenol well-known for its antioxidant and pharmaceutical properties, that can represent a renewable alternative to bisphenol A (BPA) for the synthesis of biobased polycarbonates (PC). In the presented strategy, preparation of the CM-based PC was coupled with chemical recycling of the fossil-based BPA polycarbonate (BPA-PC) conducting a two-steps trans-polymerization that replaces BPA monomer with CM or its tetrahydrogenated colorless product (THCM). In the first step of synthetic strategy, depolymerization of commercial BPA-PC was carried out with phenol as nucleophile, according to our previous procedure based on zinc derivatives and ionic liquids as catalysts, thus producing quantitatively diphenyl carbonate (DPC) e BPA. In the second step, DPC underwent a melt transesterification with CM or THCM monomers affording the corresponding bio-based polycarbonates, CM-PC and THCM-PC, respectively. THCM was prepared by reducing natural bis-phenol with cyclohexene as a hydrogen donor and characterized by 1H-NMR and MS techniques. Polymerization reactions were monitored by infrared spectroscopy and average molecular weights and dispersity of the two biobased polymers THCM-PC and CM-PC were determined by means of gel permeation chromatography (GPC). Optical properties of the prepared polymers were also measured.

Concerning synthesis of new biobased polycarbonates with curcumin in replacement of bisphenol a and recycled diphenyl carbonate as example of circular economy

De Leo V.
;
Casiello M.;Cotugno P.;Catucci L.;Nacci A.;D'Accolti L.
2021-01-01

Abstract

Curcumin (CM) is a natural polyphenol well-known for its antioxidant and pharmaceutical properties, that can represent a renewable alternative to bisphenol A (BPA) for the synthesis of biobased polycarbonates (PC). In the presented strategy, preparation of the CM-based PC was coupled with chemical recycling of the fossil-based BPA polycarbonate (BPA-PC) conducting a two-steps trans-polymerization that replaces BPA monomer with CM or its tetrahydrogenated colorless product (THCM). In the first step of synthetic strategy, depolymerization of commercial BPA-PC was carried out with phenol as nucleophile, according to our previous procedure based on zinc derivatives and ionic liquids as catalysts, thus producing quantitatively diphenyl carbonate (DPC) e BPA. In the second step, DPC underwent a melt transesterification with CM or THCM monomers affording the corresponding bio-based polycarbonates, CM-PC and THCM-PC, respectively. THCM was prepared by reducing natural bis-phenol with cyclohexene as a hydrogen donor and characterized by 1H-NMR and MS techniques. Polymerization reactions were monitored by infrared spectroscopy and average molecular weights and dispersity of the two biobased polymers THCM-PC and CM-PC were determined by means of gel permeation chromatography (GPC). Optical properties of the prepared polymers were also measured.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/365451
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