氟代脱硝合成芳香族氟化物的研究

【作者】 叶方青；

【导师】 吕春绪； 蔡春；

【作者基本信息】 南京理工大学 ， 应用化学， 2004， 硕士

【摘要】 氟代脱硝反应是合成芳香氟化物的有效方法之一，与已经工业化的其它方法相比较而言，它具有很多优点。与普通的Balz-Schiemman反应相比较，它具有安全，简单的优点。与卤素交换相比较，硝基比卤素具有更大的离去性，而且硝基比卤素具有更大的诱导效应，使得其在相同的活化条件下更容易发生反应。氟代脱硝的一个重要优势在于其可以合成卤素交换不易合成的间位芳香氟化物。 本文主要以间二硝基苯为反应底物，合成间硝基氟苯。通过对氟代脱硝反应的单因素实验分析，发现溶剂、催化剂、反应时间等因素均会对反应效果产生影响。通过比较，初步选择了比较优化的反应条件，反应结果的转化率与选择性均有不同程度的提高。介绍了制各氟代季铵盐的简便方法，并从该反应中发现了不必要的副反应。用合成的氟代季铵盐作为反应的氟离子源比较了其反应性。为了充分了解氟代脱硝反应，采用气相色谱跟踪了反应进程，并分析了各种体系。从机理角度来分析氟代脱硝反应。更多还原

【Abstract】 Fluorodenitration is one of the effective methods for synthesizing fluoroaromatic compounds. Compared with other methods, which have been applied in industry, it has many advantages. Compared with common Balz-Schiemann reaction, it has the character of safety and simple. Compared with Halogen-exchange reaction, its notro group has more abilities to leave, and more inductive effect than halogen group. With these advantages, fluorodenitration can be easier to take place than Halogen-exchange reaction under the same activation condition. One of its important advantages is that meta-fluoroaromatic compounds can be synthesized by fluorodenitration while it can’t be synthesized by Halogen-exchange.In this paper, meta-dinitrobenzene was used as substrate to synthesize 3 -nitro-fluorobezene. Through the analyzing the experiments about single effect factors on fluorodenitration, we found that fluorodenitration can be affected by solvent, catalyst, reaction time and so on. Through comparison, we choose the optimize reaction conditions on the fluorodenitration and the results are shown that these conditions are very good. We introduced one simple method of synthesizing quaternary ammonium fluoride and found some unnecessary side reactions in the reaction. We compared the reaction character of the quaternary ammonium fluoride that was synthesized by us with other compounds. In order to know more of fluorodenitration, we used Gas Chromatography to detect the process of fluorodenitration and analyzed various systems. We also analyzed fluorodenitration from the mechanism.更多还原