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茚-1,3-二酮制备与表征综合实验设计与教学实践

Design and Teaching Practice of Indan-1,3-diones Preparation and Characterization Experiment

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【作者】 靳晓宁姜爽张万东

【Author】 JIN Xiao-Ning;JIANG Shuang;ZHANG Wan-Dong;School of Science, Tianjin University, National Demonstration Center for Experimental Chemistry & Chemical Engineering Education(Tianjin University), National Virtual Simulation Experimental Teaching Center for Chemistry & Chemical Engineering Education(Tianjin University);

【通讯作者】 张万东;

【机构】 天津大学理学院化学化工国家级实验教学示范中心(天津大学)化学化工国家级虚拟仿真实验教学中心(天津大学)

【摘要】 为将混合酯的缩合反应引入本科化学实验教学中,设计了综合化学实验——茚-1,3-二酮的制备实验。该实验以邻苯二甲酸二乙酯和乙酸乙酯为原料,乙醇钠为催化剂,经Claisen酯缩合反应、酸性条件下酯水解反应、热脱羧反应制备了茚-1,3-二酮。实验涉及回流、蒸馏、重结晶、减压过滤、恒温控制和恒压滴液等基本操作,并利用熔点测定、红外光谱及核磁共振氢谱、碳谱等对产品结构进行了表征。本实验综合运用了有机合成、产物分离和结构表征等技术手段,对于培养本科生的多步合成能力及波谱解析能力具有很好的教学效果。

【Abstract】 In order to introduce the Claisen condensation reaction of mixed ester to undergraduate experimental class, a comprehensive chemistry experiment about the preparation of indan-1,3-diones was designed and applied in practice. Using diethyl phthalate and ethyl acetate as starting materials under the catalysis of sodium ethoxide, indan-1,3-diones was successfully synthesized through a three-steps procedure including Claisen condensation, ester hydrolysis, and decarboxylation reaction. The product was characterized through melting point measurement and spectroscopic study including IR, 1H NMR and 13C NMR. The experiment process involves a series of basic operation procedures containing heating reflux, distillation, recrystallization, vacuum filtration, temperature control, and constant pressure drop. In this experiment, comprehensive experimental techniques concerning organic synthesis, product separation and structure characterization are utilized, which is beneficial to improve undergraduates’ multi-step synthesis ability and spectrum analysis ability.

【基金】 2020年天津市普通高等学校本科教学质量与教学改革研究计划项目(B201005607)
  • 【文献出处】 化学教育(中英文) ,Chinese Journal of Chemical Education , 编辑部邮箱 ,2023年10期
  • 【分类号】O625.42-4;G642.4
  • 【下载频次】65
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