大学化学 >> 2026, Vol. 41 >> Issue (5): 159-169.doi: 10.12461/PKU.DXHX202511049

所属专题： 第5届全国大学生化学实验创新设计大赛

专题 上一篇    

二苯甲烷制备实验改进研究与拓展

谭淅, 陈春宏, 冷丽佳, 张玉龙   

  1. 重庆师范大学化学学院, 重庆 401331
  • 收稿日期:2025-11-10 录用日期:2026-02-25 发布日期:2026-05-21
  • 通讯作者: 张玉龙 E-mail:20190040@cqnu.edu.cn Yulong Zhang
  • 基金资助:
    国家自然科学基金(22401031)

Improvement and extension of diphenylmethane synthesis experiment

Xi Tan, Chunhong Chen, Lijia Leng, Yulong Zhang   

  1. College of Chemistry, Chongqing Normal University, Chongqing 401331, China
  • Received:2025-11-10 Accepted:2026-02-25 Published:2026-05-21
  • Contact: Yulong Zhang E-mail:20190040@cqnu.edu.cn

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摘要： 羰基还原反应是有机化学课程教学中的重点内容。当前本科基础实验教学中主要通过具有中国特色的黄鸣龙还原方法实现。该实验在本科教学实施过程中暴露出水合肼试剂毒性大、高温副产物多、后处理操作难和实验安全性低等问题。针对上述问题，我们对二苯甲烷制备实验进行如下改进：1) 采用绿色安全的聚甲基氢硅氧烷(PMHS)-FeCl3还原体系替代N2H4·H2O-KOH；2) 将高温易释放有毒且刺激性气味物质的二聚乙二醇溶剂替换成稳定易处理的1,2-二氯乙烷；3) 反应温度可由140-195 ℃的高温降低到70 ℃；4) 反应时间由4 h缩减至1 h；5) 采用研磨+抽滤的后处理方法替代操作复杂且不安全的减压蒸馏。此外，通过引入薄层色谱及柱色谱，红外及核磁表征等环节，基于药物分子酮洛芬进行选择性脱氧还原实验，设计成8学时综合性创新实验，提高了学生化学综合素养的培养。

关键词: 脱氧还原反应, Wolff-Kishner-黄鸣龙还原反应, 二苯甲酮, 绿色化学, 实验改进与创新

Abstract: Carbonyl reduction reactions constitute a fundamental component in organic chemistry education. In current undergraduate laboratory instruction, this transformation is predominantly demonstrated through the Huang-Minlon reduction method, a pivotal method developed in China. However, this conventional experiment presents several pedagogical challenges, including the use of highly toxic hydrazine hydrate, excessive high-temperature byproduct formation, cumbersome workup procedures, and notable safety concerns. To address these limitations, we have implemented the following modifications to the diphenylmethane synthesis experiment: 1) replacement of the N2H4·H2O-KOH system with an environmentally benign Polymethylhydrosiloxane (PMHS)-FeCl3 reduction system; 2) substitution of hazardous diethylene glycol solvent (which releases toxic and irritating fumes at elevated temperatures) with stable and easily handled 1,2-dichloroethane; 3) reduction of reaction temperature from 140–195 to 70 ℃; 4) shortening of reaction duration from 4 to 1 h; and 5) adoption of a simplified workup procedure involving grinding and vacuum filtration instead of complex and potentially hazardous reduced-pressure distillation. Furthermore, by incorporating analytical techniques such as thin-layer chromatography, column chromatography purification, and spectroscopic characterization (Infrared Spectroscopy (IR) and Nuclear Magnetic Resonance (NMR)), we have developed this into an 8-hour comprehensive experiment. The extended protocol includes selective deoxygenative reduction of the pharmaceutical compound ketoprofen, thereby enhancing students’ comprehensive chemical competencies.

Key words: Deoxygenative reduction, Wolff-Kishner-Huang Minlon-reduction reaction, Benzophenone, Green chemistry, Experimental improvement and innovation