大学化学 >> 2025, Vol. 40 >> Issue (7): 277-285.doi: 10.12461/PKU.DXHX202408010

所属专题： 有机化学课程与实验教学(2024)

化学实验 上一篇    下一篇

外消旋酒石酸拆分实验的改进

程岚军, 王欣媛, 安洁, 吴祥, 朱成峰, 付延明, 李有桂   

  1. 合肥工业大学化学与化工学院, 合肥 230009
  • 收稿日期:2024-08-10 录用日期:2024-11-04 发布日期:2025-07-01
  • 通讯作者: 李有桂 E-mail:liyg@hfut.edu.cn
  • 基金资助:
    安徽省研究生教育质量工程项目(2023lhpysfjd005)

Improvement of the Resolution Experiment of Racemic Tartaric Acid

Lanjun Cheng, Xinyuan Wang, Jie An, Xiang Wu, Chengfeng Zhu, Yanming Fu, Yougui Li   

  1. School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China
  • Received:2024-08-10 Accepted:2024-11-04 Published:2025-07-01
  • Contact: Yougui Li E-mail:liyg@hfut.edu.cn

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摘要： 酒石酸及其衍生物可作为手性拆分剂拆分外消旋化合物，现有拆分实验较复杂且现象不直观。本实验为改进实验，以苯胺与外消旋酒石酸反应生成铵盐，通过拆分试剂、结晶溶剂和温度等反应条件的优化，获得了可视化的L型和D型酒石酸苯胺铵盐晶体，分别再进行碱性水解，酸化获得D-(−)-酒石酸和L-(+)-酒石酸。运用圆二色谱、旋光仪和核磁共振波谱等多种手段对拆分的晶体进行表征和确证。本改进实验立足于通过宏观现象反映微观本质，便于学生对手性(分子)概念的理解和掌握。

关键词: 外消酒石酸, 苯胺, 酒石酸铵盐, 结晶, 手性拆分

Abstract: Tartaric acid and its derivatives are commonly adopted as chiral resolving agents for the separation of racemic compounds. However, existing separation experiments tend to be complex with the not easily observed phenomena. This study presents an improved experiment in which aniline is reacted with racemic tartaric acid to form ammonium salts. By optimizing reaction conditions, including separation reagents, crystallization solvents, and temperature, visible L-type and D-type tartaric acid aniline ammonium salt crystals are obtained. These crystals are then subjected to alkaline hydrolysis and the following acidification to yield D-(−)-tartaric acid and L-(+)-tartaric acid. The separated crystals are further characterized and confirmed via various techniques, such as circular dichroism (CD), polarimetry, and nuclear magnetic resonance (NMR) spectroscopy. This improved experiment emphasizes the macroscopic manifestation of the microscopic chiral nature, making it easier for students to understand and grasp the concept of chirality (molecular structure).

Key words: Racemic tartaric acid, Aniline, Ammonium tartate, Crystallization, Chiral resolution