摘要：芳香族化合物（aromatic compounds ），我们一般会把一些具有芳香气的天然物质称为芳香族化合物。[1]由于其结构比较特别，所以它也被广泛地作为有机合成中间体。本次研究我主要针对使用三氯异氰脲酸来对芳香族化合物进行芳环上的一氯代反应的研究。并且将反应在不同的催化剂下进行，分别选择了对甲苯磺酸、硝酸铵和氯化铁，从而分析得到此反应的最佳配比以及衍生拓展与应用。9816
在研究当中，我们可以发现三氯异氰脲酸对于氯代反应有与生俱来的自然高选择性。通过研究我们了解到对于带有强供电子基的芳香族化合物，水相中的氯代反应可以在室温下发生，在对甲苯磺酸的催化下，一氯代物产率约为80.4~95.5%对于带有弱供电子基的芳香族化合物，在其中加入催化剂硝酸铵，反应速度较快，氯代物产率为90~96%。对于活性相对较低的芳香族化合物，使用氯化铁为催化剂，也可得到氯代产物，产率为80~86%。
本次研究的上述反应实验，都有一个共同的优点，那就是反应溶剂和试剂毒性低、条件温和、选择性高，是一种相当符合现代社会对可持续发展战略要求的氯代方法，为绿色化学的发展又增添了新气象。
关键词： 芳香族化合物；选择性；氯代反应；三氯异氰脲酸
Study on the reaction of aromatic compounds with a high selectivity of chlorine
Abstract: A kind of plant gum made from the material with aromatic smell were known as the aromatic compounds .[1] Because of its special structure, it is widely used as intermediate in organic synthesis.
This study focused on the chlorination of the aromatic compound with the use of TCCA.And the reaction is carried out in different catalysts.We chose the toluene-p-sulfuric acid,ammonium nitrate and ferric chloride.Then we analysed the proportion of this reaction and the derivative expansion and application.
In the study,we can find TCCA with high selectivity of natural birthright for chlorination reaction.Through the research we know that for the aromatic compounds with strong electro-donating groups,the aqueous chlorination reaction can occur at room temperature.Under the toluene-p-sulfuric acid as the catalysis,a chloride yield is about 80.4~95.5%.For the aromatic compounds with weakly electron-donating groups,these reaction rate is very fast under the catalysis of ammonium nitrate. The chloride yield is 90~96%.When the activity of aromatic compounds were relatively low,this reaction can also gain chlorinated product.The chloride yield is 80~86%.
The experiment of this study have a common advantage.That is the solvent and reagent in these reactions are with low toxicity,mild condition and have high selectivity,which is a great chlorinated method fits the modern social requirements of sustainable development strategy.It can create a new world in the field of green chemistry.
Key words: Aromatic compounds; Selective; Chlorinated reaction; TCCA
目 录
1 绪论 1
1.1芳香族化合物的性质与用途 1
1.1.1.1 芳香族化合物的定义 1
1.1.1.2 芳香族化合物的性质 1
1.1.2 芳香族化合物的用途 1
1.2 有机化合反应中的选择性 1
1.2.1 区域选择性 2
1.2.2 化学选择性 2
1.2.3 立体选择性 2
1.3芳香族化合物参与的绿色有机反应 3
1.4 绿色有机氧化反应 4
2 芳香族化合物高选择性一氯代反应 8
2.1对甲苯磺酸催化下苯环上的氯代反应最佳条件探索 8 芳香族化合物高选择性一氯代反应研究:http://www.751com.cn/huaxue/lunwen_8646.html