多氯甲基芳烃及其衍生物的合成研究有机化学专业论文.docxVIP

湘潭大学 湘潭大学 2010 届硕士研究生毕业论文 II II Abstract The Blanc chloromethylation reaction of arene still plays an important role in many organic reactions, which has been widely applied in synthesizing many chloromethyl aromatic hydrocarbon monomers that widely used in medicine, pesticide, paint, organic additives, polymer materials, etc. At present, there are many methods to synthesize chloromethylarene. But the yield of traditional chloromethylation reaction is usually very low. In particular, some problems about low production are still unsolved when we synthesize some polychloromethylated compounds. In this circumstance, a novel composite catalyst prepared from lewis acid, organic acid, and inorganic acid in a certain ration had been applied to synthesize some polychloromethylarenes through the chloromethylation reaction in this paper. Under atomaspheric pressure, 4,4′-bis(chloromethyl)biphenyl, 1,5-bis(chloromethyl)naphthalene, 2,4,6-tri(chloromethyl)toluene, 2,4,6-tri(chlorome- thyl)ethylbenzene, 2,4,6-tri(chloromethyl)isopropylbenzene, 2,4,6-tri(chloromethyl)- m-xylene, 2,4,6-tri(chloromethyl)mesitylene were successfully prepared from biphenyl, naphthalene, methylbenzene, ethylbenzene, cumene, m-xylene, mesitylene, respectively via polychloromethylation by using this novel composite catalyst. The factors that affect the reactions and yields were investigated systematically. It was found that this new synthetic method has many advantages such as easy manipulations, facile raw materials, high yields, mild reaction conditions, high-quality productions, which is suitable for industrialized manufacture and has potential application prospects. Furthermore, the chloromethyl functional groups of arene can be easily converted into many other useful active groups, such as -CHO, -COOH, -CH2COOH, -CH2N(CH3)2, -CN, -CH2NH2, -CH2CN, -CH2OCH3, -CH2OH, -CH2R, and so on. In order to realize material conversion and improve the performance of productions, we have tried to synthesize vari