Werlinger Francisca, Caprile Renato, Cárdenas-Toledo Valentino, Tarraff Bastián, Mesías-Salazar Ángela, Rojas René S, Martínez Javier, Trofymchuk Oleksandra S, Flores Mario E
Facultad de Ciencias Químicas y Farmacéuticas, Departamento de Química Orgánica y Fisicoquímica, Universidad de Chile, Sergio Livingstone 1007, Casilla 233, Metropolitan Region, Santiago 8380492, Chile.
Instituto de Ciencias Químicas, Facultad de Ciencias, Isla Teja, Universidad Austral de Chile, Valdivia 5090000, Chile.
ACS Omega. 2023 Jun 5;8(24):21540-21548. doi: 10.1021/acsomega.3c00623. eCollection 2023 Jun 20.
The transformation of cooking oils and their waste into polyesters is a challenge for circular chemistry. Herein, we have used epoxidized olive oil (EOO), obtained from cooking olive oil (COO), and various cyclic anhydrides (such as phthalic anhydride PA, maleic anhydride MA, and succinic anhydride SA) as raw materials for the preparation of new bio-based polyesters. For the synthesis of these materials, we have used the bis(guanidine) organocatalyst and tetrabutylammonium iodide (BuNI) as cocatalyst. The optimal reaction conditions for the preparation of poly(EOO--PA) and poly(EOO--MA) were 80 °C for 5 h using toluene as solvent; however, the synthesis of poly(EOO--SA) required more extreme reaction conditions. Furthermore, we have exclusively succeeded in obtaining the trans isomer for MA-polyester. The obtained biopolyesters were characterized by NMR, Fourier transform infrared, thermogravimetric analysis, and scanning electron microscopy analyses. Since there are few examples of functionalized and defined compounds based on olive oil, it is innovative and challenging to transform these natural-based compounds into products with high added value.
将食用油及其废弃物转化为聚酯是循环化学面临的一项挑战。在此，我们使用了由烹饪橄榄油（COO）制得的环氧橄榄油（EOO）以及各种环状酸酐（如邻苯二甲酸酐PA、马来酸酐MA和琥珀酸酐SA）作为制备新型生物基聚酯的原料。为了合成这些材料，我们使用了双（胍）有机催化剂和四丁基碘化铵（BuNI）作为助催化剂。制备聚（EOO - PA）和聚（EOO - MA）的最佳反应条件是以甲苯为溶剂，80℃反应5小时；然而，聚（EOO - SA）的合成需要更极端的反应条件。此外，我们仅成功获得了MA - 聚酯的反式异构体。通过核磁共振、傅里叶变换红外光谱、热重分析和扫描电子显微镜分析对所得生物聚酯进行了表征。由于基于橄榄油的功能化和特定化合物的例子很少，将这些天然基化合物转化为高附加值产品既具有创新性又具有挑战性。
