Ragno Daniele, Brandolese Arianna, Di Carmine Graziano, Buoso Sara, Belletti Giada, Leonardi Costanza, Bortolini Olga, Bertoldo Monica, Massi Alessandro
Department of Chemical and Pharmaceutical Sciences, University of Ferrara, Via L. Borsari, 46, 44121, Ferrara, Italy.
School of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester, M13 9PL, UK.
Chemistry. 2021 Jan 21;27(5):1839-1848. doi: 10.1002/chem.202004296. Epub 2020 Dec 21.
The polycondensation of diamines and dialdehydes promoted by an N-heterocyclic carbene (NHC) catalyst in the presence of a quinone oxidant and hexafluoro-2-propanol (HFIP) is herein presented for the synthesis of oligomeric polyamides (PAs), which are obtained with a number-average molecular weight (M ) in the range of 1.7-3.6 kg mol as determined by NMR analysis. In particular, the utilization of furanic dialdehyde monomers (2,5-diformylfuran, DFF; 5,5'-[oxybis(methylene)]bis[2-furaldehyde], OBFA) to access known and previously unreported biobased PAs is illustrated. The synthesis of higher molecular weight PAs (poly(decamethylene terephthalamide, PA10T, M = 62.8 kg mol ; poly(decamethylene 2,5-furandicarboxylamide, PA10F, M = 6.5 kg mol ) by a two-step polycondensation approach is also described. The thermal properties (TGA and DSC analyses) of the synthesized PAs are reported.
本文介绍了在醌氧化剂和六氟-2-丙醇（HFIP）存在下，由N-杂环卡宾（NHC）催化剂促进的二胺和二醛的缩聚反应，用于合成低聚聚酰胺（PA），通过NMR分析测定，其数均分子量（M）在1.7-3.6 kg·mol范围内。特别地，展示了利用呋喃二醛单体（2,5-二甲酰基呋喃，DFF；5,5'-[氧双（亚甲基）]双[2-糠醛]，OBFA）来制备已知的和以前未报道的生物基聚酰胺。还描述了通过两步缩聚方法合成更高分子量的聚酰胺（聚（癸二胺对苯二甲酰胺，PA10T，M = 62.8 kg·mol；聚（癸二胺2,5-呋喃二甲酰胺，PA10F，M = 6.5 kg·mol）。报道了合成聚酰胺的热性能（TGA和DSC分析）。
