大学化学 >> 2022, Vol. 37 >> Issue (5): 2111088.doi: 10.3866/PKU.DXHX202111088

所属专题: 第2届全国大学生化学实验创新设计竞赛

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绿色催化氧化合成邻硝基苯甲醛——一个氧化合成教学实验

李胜, 杨爽, 刘永浩, 赵子卓, 张琦, 黄治炎()   

  • 收稿日期:2021-11-30 录用日期:2021-12-07 发布日期:2022-04-11
  • 通讯作者: 黄治炎 E-mail:zyhuang@snnu.edu.cn
  • 作者简介:黄治炎, Email: zyhuang@snnu.edu.cn
  • 基金资助:
    陕西师范大学本科教学改革项目(19JG32)

Green Oxidative Synthesis of 2-Nitrobenzaldehyde: An Oxidative Synthesis Experiment for the Undergraduate Organic Laboratory

Sheng Li, Shuang Yang, Yonghao Liu, Zizhuo Zhao, Qi Zhang, Zhiyan Huang()   

  • Received:2021-11-30 Accepted:2021-12-07 Published:2022-04-11
  • Contact: Zhiyan Huang E-mail:zyhuang@snnu.edu.cn

摘要:

采用“科学问题为目标导向”的实验教学指导原则,将邻硝基苯甲醛的绿色合成工艺开发为有机化学基础实验,丰富了绿色氧化反应在实验教学中的应用。本新创实验以水溶性2-(2, 2, 6, 6-四甲基-4-亚哌啶基-1-氧化物)乙酸(简称TEMPO-COOH)为催化剂,在摩尔分数0.1%用量下,催化次氯酸钠氧化邻硝基苄醇,实现了重要有机合成中间体邻硝基苯甲醛的高选择性绿色催化合成,产率达93%,纯度 > 99%。作为本科生基础教学实验,本案例不仅涉及多种有机化学实验基本操作,还包含反应监测、结构表征、纯度分析等重要环节,同时还融入了绿色化学理念和有机合成方法学研究的实验探究过程。该新创实验所用试剂环境友好,安全性高,教学时长约为3–4 h,非常适合用于有机化学基础实验教学。以本实验方案为蓝本,结合有关氧化反应研究进展的微课学习和拓展练习,实现了理论知识与合成实践之间的有效互动,提升了化学专业本科生解决较为复杂有机合成问题的综合能力,提高了化学类人才的培养质量。

关键词: 绿色化学, 邻硝基苯甲醛, TEMPO-COOH, 次氯酸钠, 催化氧化

Abstract:

Applying scientific-issue-oriented education, the green synthetic process of 2-nitrobenzaldehyde was modified and applied as a fundamental organic experiment for oxidation reactions in undergraduate education. Selective oxidation of 2-nitrobenzyl alcohol was achieved in the presence of 0.1 mol% water-soluble 2-(1-hydroxy-2, 2, 6, 6-tetramethylpiperidin-4-ylidene) acetic acid (TEMPO-COOH) and commercially available NaClO. The corresponding 2-nitrobenzaldehyde was obtained in 93% yield and > 99% purity. This newly designed experiment includes a series of basic organic experimentation techniques and the entire classic organic synthesis process, including reaction monitor, structure characterization, purity analysis and so on. Furthermore, the principle of green chemistry and the general way of methodology study in organic chemistry were integrated. Environmentally friendly and inexpensive starting materials, as well as the 3‒4 h experiment period, make this innovative experiment suitable for undergraduate education. Based on the experimental design, the corresponding micro-lecture concerning advances in oxidation was developed and incorporated into the education program. Thus, the collaboration of theoretical study and practical operation was achieved, improving the ability of undergraduates to solve complicated issues in organic synthesis and achieving high training quality.

Key words: Green chemistry, 2-Nitrobenzaldehyde, TEMPO-COOH, NaClO, Catalytic oxidation

MSC2000: 

  • G64