摘要：21世纪以来，绿色化学的概念渐渐浮现在大家的视线之中。一氯芳香族化合物如一氯甲苯不仅是有机合成中间体，而且在医药、农药等行业均有广泛应用。氯甲苯也是以逐渐地成为氯碱工业的重中之重，它的远大前景正不停被人们开发。现在有很多合成一氯甲苯的方法，但是大部分的合成方法或多或少都有一些缺点。例如反应速度较慢，反应试剂有毒有害等等，并不符合绿色化学的理念。于是我们得出结论，对环境友好的氯代反应的研究很有必要。80759

本论文在无溶剂反应条件下以一定量的甲苯与低毒的固体氯代试剂TCCA反应。通过测试找寻最佳的催化剂的种类和用量、氯代试剂的用量、操作方式以及最优的反应时间。并且尝试在最有反应条件上研究出绿色、高效的一氯代化合物合成路线。在此反应条件下通过改变反应底物进行普适性研究。通过实验发现：在无溶剂反应条件下，采用研磨的方式反应三小时。以甲苯为原料，选用2mmol的氯化铵，当TCCA用量为6 mmol，并在后续处理时用乙酸乙酯萃取，则得到的产量最大，实际可得1。09 g无色油状物，产率为85。8%。然后在上述已优化的反应条件下，以甲苯、乙苯、间二甲苯、邻二甲苯、对二甲苯等为底物，得到产率较高维持在86。5%~93。6%之间。

毕业论文关键词： 氯代芳香族化合物；一氯甲苯；TCCA

Study on Chlorination Reaction of Aromatic Compounds in Solvent - free Condition

Abstract: Since the 21st century, the concept of green chemistry has gradually emerged in the sight of everyone。 Environmental protection is also an urgent problem, the need for green chemistry also increased。 Chlorinated aromatic compounds such as monochlorotallyl is not only organic synthesis intermediates, but also widely used in various pharmaceuticals, dyes and pesticides and other industries。 Chlorotoluene is also gradually become the top priority of chlor-alkali industry, its great prospects are being developed by people。 There are many ways to synthesize monochlorotoluene, but most of the synthetic methods have more or less shortcomings。 For example, the reaction rate is slow, the reaction reagent is toxic and harmful, etc。, does not meet the green chemistry concept。 Therefore, it is necessary to study the environment-friendly chlorination reaction。

In this paper, a certain amount of toluene was reacted with low-toxic solid chlorine reagent TCCA under solvent-free reaction。 By testing the type of catalyst and the optimal amount of catalyst, TCCA dosage, mode of operation, optimize the reaction time。 And try to develop the green and efficient monochloride compound synthesis route under the most reaction conditions。 Under this reaction condition, universal study was carried out by changing the reaction substrate。 Experiments show that: in the absence of solvent reaction conditions, the use of grinding method。 With toluene as raw material, 2 mmol of ammonium chloride was used。 When TCCA was used in an amount of 6 mmol and extracted with ethyl acetate at the time of subsequent treatment, the yield was the largest, and 1。09 g of a colorless oil was actually obtained in a yield of 85。8 %。 And then under the optimized reaction conditions described above, toluene, ethylbenzene, p-xylene。 M-xylene, o-xylene and so on as the substrate, the yield of monochloride is higher, the yield is between 86。5% and 93。6%。

Key words: chlorinated aromatic compounds; monochlorotoluene; TCCA

目  录

1 绪论 1

1。1 芳香族的卤代化合物及其重要性 1

1。1。1 芳香族的氯化物及其应用 1

1。1。2芳香族的溴化物的应用