Herein, an ionic liquid, 1-[1-(ethoxycarbonyl)-2-oxopropyl]-3-methylimidazolium chloride (1,3-(CO)₂IL-HCl), was synthesized and used as a donor of hydrogen chloride (HCl) to participate in an organic reaction. Interestingly, the simultaneously generated 1-[1-(ethoxycarbonyl)-2-oxopropyl]-3-methylimidazolium inner salt (1,3-(CO)₂IL) can then capture HCl from another reaction that produces HCl as a waste. This allowed us to use IL as a shuttle to transfer waste HCl from the first reaction to the second one that needs HCl as one of the reactants. In a proof-of-concept experiment, a ring-opening reaction of glycidyl phenyl ether with released HCl was selected; and the waste HCl comes from an alcoholysis of benzoyl chloride with ethanol. 1,3-(CO)₂IL can be used as a shuttle for transferring HCl five times without evident decline of its performance. Mechanism investigation revealed that the interconversion of keto and enol forms in 1,3-(CO)₂IL and a moderate pK_a value are keys to ensuring the release and capture of HCl.

中文翻译：

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离子液体作为释放和捕获氯化氢的穿梭机：利用有机反应中产生的废HCl的新方法

本文合成了离子液体 1-[1-(乙氧基羰基)-2-氧代丙基]-3-甲基咪唑鎓氯化物 (1,3-(CO) ₂ IL-HCl)，并用作氯化氢 (HCl) 的供体。 ）参与有机反应。有趣的是，同时生成的 1-[1-(乙氧基羰基)-2-氧代丙基]-3-甲基咪唑鎓内盐 (1,3-(CO) ₂ IL) 可以从另一个产生 HCl 废物的反应中捕获 HCl。这使我们能够使用 IL 作为穿梭机，将废 HCl 从第一个反应转移到需要 HCl 作为反应物的第二个反应。在概念验证实验中，选择了缩水甘油基苯基醚与释放的 HCl 的开环反应；废HCl来自苯甲酰氯与乙醇的醇解。 1,3-(CO) ₂ IL 可作为梭子传输 HCl 5 次，其性能没有明显下降。机理研究表明，1,3-(CO) ₂ IL 中酮和烯醇形式的相互转化和适度的 p K _a值是确保 HCl 释放和捕获的关键。