Mechanistic Considerations of Efficient Esterification of Starch with Propionic Anhydride/Lauric Acid in the Green Solvent Imidazole,Macromolecular Chemistry and Physics

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Mechanistic Considerations of Efficient Esterification of Starch with Propionic Anhydride/Lauric Acid in the Green Solvent Imidazole
Macromolecular Chemistry and Physics ( IF 2.5 ) Pub Date : 2020-11-12 , DOI: 10.1002/macp.202000264
Sascha Blohm ₁ , Thomas Heinze ₁

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Starch esters have become increasingly attractive as sustainable materials. Instead of carboxylic acid chlorides, mixtures of carboxylic acid anhydrides and carboxylic acids are used to synthesize highly substituted starch esters efficiently applying the new starch solvent imidazole. The reaction is a promising alternative to the existing protocols and leads to thermoplastic mixed starch esters. The mechanism for the reaction path is elucidated by the conversion of starch with propionic anhydride/lauric acid in molten imidazole and various model reactions applying Fourier transform infrared spectroscopy and NMR spectroscopic measurements. Mixed starch esters are obtained bearing not only propionate groups introduced by the reactive anhydride but also moieties originating from the lauric acid. The propionic anhydride is shown to react with imidazole to form the corresponding imidazolide. Moreover, the imidazolide is in equilibrium with the lauric acid to form the corresponding imidazolide as well.

中文翻译：

在绿色溶剂咪唑中用丙酸酐/月桂酸有效酯化淀粉的机理研究

淀粉酯作为可持续材料越来越具有吸引力。代替羧酸氯化物，使用羧酸酐和羧酸的混合物有效地应用新型淀粉溶剂咪唑来合成高度取代的淀粉酯。该反应是现有方案的有希望的替代方案，并导致热塑性混合淀粉酯。通过在熔融的咪唑中用丙酸酐/月桂酸将淀粉转化，以及应用傅里叶变换红外光谱和NMR光谱测量的各种模型反应，阐明了反应路径的机理。得到的混合淀粉酯不仅带有由反应性酸酐引入的丙酸酯基团，而且还带有源自月桂酸的部分。显示丙酸酐与咪唑反应形成相应的咪唑化物。此外，咪唑化物与月桂酸处于平衡状态，从而也形成相应的咪唑化物。

更新日期：2020-12-07

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