Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether
Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether
复制标题
含有两个或三个由三氟乙基缩水甘油醚启用的不同官能团的甘油衍生溶剂
DOI：
10.1002/aic.17533
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发表时间：
2021
期刊：
影响因子：
3.7
通讯作者：
Bara, Jason E.
中科院分区：
文献类型：
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作者：
Qian, Shuai;Liu, Xiaoyang;Turner, Christoffer Heath;Bara, Jason E.
将环氧氯丙烷转化为缩水甘油醚可产生多功能前体，这些前体可转化为各种具有甘油骨架的分子种类，从而能够设计具有高度定制功能的分子。 2,2,2-三氟乙基缩水甘油醚（TFGE，IUPAC 名称：2-[(2,2,2-三氟乙氧基)甲基]环氧乙烷，CAS# 1535-91-7）的合成经过优化，可提供高产率/选择性和良好的“绿色指标”。然后，TFGE 被用作合成不对称甘油 1,3-二醚-2-醇衍生物的平台分子，随后将其转化为 1,2,3-三醚或 1,3-二醚-2-酮。测量了每个分子的密度、粘度和 CO2 溶解度，并与其他甘油衍生化合物以及具有相似官能团的化合物进行比较。此外，还进行了量子化学计算，以了解这些分子吸收二氧化碳的结构-性质-性能关系。根据这项工作的结果，我们预计 TFGE（和类似的缩水甘油醚）将为绿色溶剂和更复杂化合物的前体的分子设计提供极大的灵活性。
Conversion of epichlorohydrin to glycidyl ethers creates versatile precursors that can be transformed into a variety of molecular species with glycerol skeletons, enabling the design of molecules with highly tailored functionalities. The synthesis of 2,2,2‐trifluoroethyl glycidyl ether (TFGE, IUPAC name: 2‐[(2,2,2‐trifluoroethoxy)methyl]oxirane, CAS# 1535‐91‐7) was optimized to provide high yield/selectivity and good “green metrics.” TFGE was then used as a platform molecule in the synthesis of asymmetric glycerol 1,3‐diether‐2‐alcohol derivatives, which were subsequently transformed to 1,2,3‐triethers or 1,3‐diether‐2‐ketones. The density, viscosity, and CO2solubility of each molecule were measured and compared with those of other glycerol‐derived compounds as well as compounds with similar functional groups. Furthermore, quantum chemical calculations were performed to understand the structure–property–performance relationships of these molecules for CO2absorption. Based on the results in this work, we foresee that TFGE (and similar glycidyl ethers) would offer great flexibility in molecular design of green solvents and precursors to more complex compounds.