大学化学 >> 2025, Vol. 40 >> Issue (3): 342-348.doi: 10.12461/PKU.DXHX202405181

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综合有机化学实验：磷钨酸催化三苯甲醇的直接转化制备肟醚类化合物

韩峰, 万福贤, 李映, 张丛丛, 张元红, 苗成霞   

  1. 山东农业大学化学与材料科学学院, 山东 泰安 271018
  • 收稿日期:2024-05-27 录用日期:2024-09-02 发布日期:2025-03-19
  • 通讯作者: 张元红, 苗成霞 E-mail:chxmiao@sdau.edu.cn;yhzhang@sdau.edu.cn
  • 基金资助:
    山东省研究生优质课程项目(SDYKC2023032)；山东省研究生优质专业学位教学案例库项目(SDYAL2023040)；山东农业大学研究生教育质量提升计划(2022SZ002)；山东化学教指委项目(SDHX-YB-2022-15)

Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers

Feng Han, Fuxian Wan, Ying Li, Congcong Zhang, Yuanhong Zhang, Chengxia Miao   

  1. College of Chemistry and Material Science, Shandong Agricultural University, Tai'an 271018, Shandong Province, China
  • Received:2024-05-27 Accepted:2024-09-02 Published:2025-03-19
  • Contact: Yuanhong Zhang, Chengxia Miao E-mail:chxmiao@sdau.edu.cn;yhzhang@sdau.edu.cn

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摘要： 聚焦学科前沿，结合教师的科研成果，设计了一项综合有机化学实验——磷钨酸催化三苯甲醇的直接转化制备肟醚类化合物。实验以绿色固体酸磷钨酸为催化剂，碳酸二甲酯为绿色溶剂，用三苯甲醇与二苯甲酮肟在室温下反应生成肟醚和水，并考察了催化剂用量对产率的影响。此外，结合催化转化验证实验和紫外光谱分析结果推断了反应机理——亲核取代反应碳正离子历程。该实验具有绿色环保、反应条件温和、前沿新颖等优点，不仅能够提升学生的实验技能、综合能力和环保意识，还可以激发学生的科研兴趣和创新思维，适合作为高校教学实验。

关键词: 醇的直接转化, 绿色化学, 磷钨酸, 亲核取代反应

Abstract: This study introduces a novel and environmentally friendly organic chemistry experiment that integrates cutting-edge research into academic practice. The experiment involves the direct conversion of triphenylmethanol to oxime ethers, catalyzed by phosphotungstic acid, a green solid acid, with dimethyl carbonate serving as a sustainable solvent. At room temperature, triphenylmethanol reacts with benzophenone oxime to yield oxime ethers and water. The influence of catalyst concentration on the reaction yield is systematically examined. Furthermore, the reaction mechanism — specifically, a nucleophilic substitution proceeding through a carbocation intermediate — is inferred based on catalytic conversion verification and UV spectroscopic analysis. This experiment offers several advantages, including green chemistry principles, mild reaction conditions, and relevance to current research. It enhances students’ experimental competencies, fosters environmental awareness, and sparks interest in scientific research and innovation, making it highly suitable for university-level instruction.

Key words: Direct conversion of alcohols, Green chemistry, Phosphotungstic acid, Nucleophilic substitution reaction