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Amino acids as bio-organocatalysts in ring-opening copolymerization for eco-friendly synthesis of biobased oligomers from vegetable oils
dc.contributor.author | Werlinger, Francisca | |
dc.contributor.author | Beroíza-Duhart, Monserrat | |
dc.contributor.author | Douglas-Gallardo, Oscar A. | |
dc.contributor.author | Oyarzo-Aro, Silvia | |
dc.contributor.author | Valenzuela, Maria Luisa | |
dc.contributor.author | Trofymchuk, Oleksandra S. | |
dc.contributor.author | Flores, Mario E. | |
dc.contributor.author | Martínez, Javier | |
dc.date.accessioned | 2024-06-19T04:41:34Z | |
dc.date.available | 2024-06-19T04:41:34Z | |
dc.date.issued | 2024 | |
dc.identifier | 10.1039/d4ob00339j | |
dc.identifier.issn | 14770520 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12728/11324 | |
dc.description.abstract | Herein, we present an innovative synthetic approach for producing a diverse set of biobased oligomers. This method begins with olive oil and employs a wide variety of commercially available amino acids (AAs) as bio-organocatalysts, in addition to tetrabutylammonium iodide (TBAI) as a cocatalyst, to synthesize various biobased oligomers. These biobased oligomers were strategically prepared starting from epoxidized olive oil (EOO) and a variety of cyclic anhydrides (phthalic, PA; maleic, MA; succinic, SA; and glutaric, GA). Among the amino acids tested as bio-organocatalysts, l-glutamic acid (l-Glu) showed the best performance for the synthesis of both poly(EOO-co-PA) and poly(EOO-co-MA), exhibiting 100% conversion at 80 °C in 2 hours, whereas the formation of poly(EOO-co-SA) and poly(EOO-co-GA) required more extreme reaction conditions (72 hours under toluene reflux conditions). Likewise, we have succeeded in obtaining the trans isomer exclusively for the MA based-oligomer within the same synthetic framework. The obtained oligomers were extensively characterized using techniques including NMR, FT-IR, GPC and TGA. A series of computational simulations based on density functional theory (DFT) and post-Hartree Fock (post-HF) methods were performed to corroborate our experimental findings and to obtain an understanding of the reaction mechanisms. © 2024 The Royal Society of Chemistry. | es_ES |
dc.description.sponsorship | Fondo Nacional de Desarrollo Científico y Tecnológico, FONDECYT, (3220023, 1220241, 11230124, FOVI230027); Fondo Nacional de Desarrollo Científico y Tecnológico, FONDECYT | es_ES |
dc.language.iso | en | es_ES |
dc.publisher | Royal Society of Chemistry | es_ES |
dc.title | Amino acids as bio-organocatalysts in ring-opening copolymerization for eco-friendly synthesis of biobased oligomers from vegetable oils | es_ES |
dc.type | Article | es_ES |