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摘要：随着人们对环境保护意识的日益增强，发展环境友好型的绿色化学已成为化学工业研究中的前沿课题。芳香族卤代物是重要的有机物中间体，应用十分广泛。芳香族化合物氯代产物的合成通常污染大，生产工艺复杂，危险性较高，所以发展廉价易得污染小，工艺简单安全的合成方法非常必要。36585
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论文首先以正己烷作溶剂，在一定量的甲苯中，加入三氯异氰尿酸（TCCA），调整各种反应物的比例，提高氯代物产率。优化反应时间，保持加热搅拌回流反应，尝试在此基础上发展绿色、高效、快速的氯代方法，提高氯代物产率。优化过的反应条件为：甲苯与TCCA摩尔比为3:1，溶剂正己烷的含量为10 mL，经简单后处理，产率为93.4 %。然后针对这些条件在芳香族其他化合物的普适性做了一定的研究。实验表明，当苯环上的取代基为供电子基团时取代反应较容易发生，一氯代产物产率较高，如甲基、乙基、甲氧基等，产率最高可达到95.7%。而当取代基为吸电子基团时取代反应就相对难以进行，且取代基吸电子能力越强，取代反应越难进行，产率越低。
毕业论文关键词：甲苯；三聚异氰尿酸；绿色化学；快速卤代反应.
Fast halogenated reaction about aromatic compounds
Abstract: With the growing awareness of environmental protection, developing environmentally friendly green chemistry has become a frontier topic in the study of the chemical industry. Aromatic halogen content is an important organic intermediates, application is very extensive. The synthesis of chlorinated aromatic compounds product usually leads to large pollution, and the production process is complex. Besides, the risk is high. So to develop a synthesis method which cause low pollution, and is easy operating and safe is very necessary.
Firstly, Hexane is used as solvent. And a certain amount of toluene and TCCA was put into three-necked flask. Then the ratio of reactants was adjusted to increase the yield of chlorinated products. Besides, the reaction time was also adjusted. Try to base on these conditions developing a green, efficient and fast method. The yield could be improved then. Conditions which has been adjusted are as follows: The molar amount of toluene is three times bigger than TCCA; the volume of hexane was set as 10 mL. Under these conditions, the yield reached 93.4%.Then substrate was changed to other aromatic derivatives. Experimental results showed a phenomenon. If the substituent on the benzene ring is electron-donor groups such as methyl, ethyl, methoxy, the substitution reaction will be likely to happen, and you can get a high yield. What’s more the highest yield can reach 95.7%. But if the substituent is electron-withdrawing group substitution reaction is relatively difficult, and the stronger ability electron-withdrawing substituent has, the harder the reaction is, which caused lower the yield.
Key words: toluene; trichloroisocyanuric acid; green chemistry; fast halogenated reaction
目 录
1 芳香族氯代物性质及用途1
1.1芳香族卤代物的合成方法1
1.1.1 芳香族化合物卤代反应主要卤代试剂1
1.1.2卤代反应合成方法举例1
1.2芳香族氯代物的性质及用途2
1.2.1芳香族氯代物的性质2
1.2.2芳香族氯代物的用途2
1.3芳香族化合物氯代反应的催化剂3
1.3.1以路易斯酸为催化剂3
1.3.2以沸石分子筛为催化剂4
1.3.3以金属氯化物为催化剂5
1.3.4以三氯化铁为催化剂6
1.4 TCCA的性质及用途6
1.4.1 TCCA的性质6
1.4.2 TCCA的用途7
1.5 本论文的研究意义8
2 芳香族化合物快速氯代反应的研究 9
2.1简单有机酸催化下的绿色一氯代反应最佳条件探索9
2.1.1 结果与讨论9
2.1.2 实验部分16
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