Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy
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 bio-based polycarbonates (PC). In the presented strategy, preparation of the CM-based PC was coupled with chemical...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-01-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/13/3/361 |
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| author | Vincenzo De Leo Michele Casiello Giuseppe Deluca Pietro Cotugno Lucia Catucci Angelo Nacci Caterina Fusco Lucia D’Accolti |
| author_facet | Vincenzo De Leo Michele Casiello Giuseppe Deluca Pietro Cotugno Lucia Catucci Angelo Nacci Caterina Fusco Lucia D’Accolti |
| author_sort | Vincenzo De Leo |
| collection | DOAJ |
| description | 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 bio-based 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 <sup>1</sup>H-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. |
| first_indexed | 2024-03-09T03:52:39Z |
| format | Article |
| id | doaj.art-9cea47193928410b921ba3fe12e66ab3 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-09T03:52:39Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-9cea47193928410b921ba3fe12e66ab32023-12-03T14:25:36ZengMDPI AGPolymers2073-43602021-01-0113336110.3390/polym13030361Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular EconomyVincenzo De Leo0Michele Casiello1Giuseppe Deluca2Pietro Cotugno3Lucia Catucci4Angelo Nacci5Caterina Fusco6Lucia D’Accolti7Department of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, ItalyDepartment of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, ItalyDepartment of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, ItalyDepartment of Biology, University of Bari, Via Orabona 4, 70126 Bari, ItalyDepartment of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, ItalyDepartment of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, ItalyICCOM-CNR, Istituto di Chimica dei Composti Organometallici, Bari Section, Via Orabona 4, 70125 Bari, ItalyDepartment of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, ItalyCurcumin (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 bio-based 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 <sup>1</sup>H-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.https://www.mdpi.com/2073-4360/13/3/361curcumintetrahydrocurcuminpolycarbonatetrans polymerizationrecycled diphenyl carbonaterecycled bisphenol A |
| spellingShingle | Vincenzo De Leo Michele Casiello Giuseppe Deluca Pietro Cotugno Lucia Catucci Angelo Nacci Caterina Fusco Lucia D’Accolti Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy Polymers curcumin tetrahydrocurcumin polycarbonate trans polymerization recycled diphenyl carbonate recycled bisphenol A |
| title | Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy |
| title_full | Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy |
| title_fullStr | Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy |
| title_full_unstemmed | Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy |
| title_short | Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol A and Recycled Diphenyl Carbonate as Example of Circular Economy |
| title_sort | concerning synthesis of new biobased polycarbonates with curcumin in replacement of bisphenol a and recycled diphenyl carbonate as example of circular economy |
| topic | curcumin tetrahydrocurcumin polycarbonate trans polymerization recycled diphenyl carbonate recycled bisphenol A |
| url | https://www.mdpi.com/2073-4360/13/3/361 |
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