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摘要：α，α-二氯代羰基化合物是一类重要的有机合成中间体，可作为合成砌块。但现有文献关于α，α-二氯代反应的报道比较少，进一步发展制备二氯代物的方法，将使二氯代羰基化合物得到更好的应用。而随着绿色化学的深入人心，发展接近绿色化学要求的氯代反应更成为了重要的研究内容。34723
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此次研究主要以乙酸乙酯为溶剂，以低毒的TCCA为氯代试剂，以氯化胆碱为催化剂，研究了苯乙酮在室温下的氯代反应。通过调整苯乙酮与TCCA的摩尔比，优化反应时间，改变氯化胆碱和乙酸乙酯的用量来探索环境友好型溶剂中氯代反应最佳反应条件。研究表明，当苯乙酮与TCCA的摩尔比为4：3，氯化胆碱为2.15 mmol，乙酸乙酯为5 mL时，二氯代产物产率达到最大值，为93.1%。对于苯乙酮类化合物的氯代反应研究表明，二氯代产物产率在80～96%。
毕业论文关键词：苯乙酮类化合物；氯化胆碱；氯代反应；绿色化学；
The study of chlorination in environmental friendly solvent
Abstract: α,α-Dichloro carbonyl compounds are an important class of organic synthesis intermediates and are usually used as synthetic blocks. But there is few papers about α,α-dichlorination reactions. The further development of the method for preparing dichloro compounds will improve the application of dichloro-carbonyl compounds. With the popularity of green chemistry，the development of green chemistry to chlorination reactions have become an important research content.
Ethyl acetate as solvent，TCCA with low toxicity as chlorinated reagents and choline chloride as catalyst were used to study the chlorination reactions of acetophenone at room temperature. The conditions of chlorination reactions in green solvents were optimized by adjusting the molar ratios of acetophenone and TCCA， the reaction time and the amounts of choline chloride and ethyl acetate. The research showed that when the molar ratio of acetophenone and TCCA being 4 to 3，the amount of choline chloride being 2.15 mmol and the amount of ethyl acetate being 5 mL，the yield of α,α-dichlorides reached the maximum value and it was 93.1%. The research on the chlorination reactions of acetophenones showed that the yields of α,α-dichloro carbonyl compounds were 80 to 96 per cent.
Key words: acetophenones；choline chloride；chlorination；green chemistry
目 录
1 绪论 1
1.1 季铵盐作为催化剂的重要作用• 1
1.1.1 季铵盐的性质及用途•• 1
1.1.2 季铵盐在酸性条件下的催化•• 1
1.1.3 季铵盐在碱性条件下的催化•• 2
1.1.4 季铵盐在中性条件下的催化•• 3
1.2 TCCA的重要性 5
1.2.1 TCCA的性质及用途• 5
1.2.2 TCCA的氧化作用6
1.2.3 TCCA的除菌作用6
1.2.4 TCCA的氯化作用8
1.3 小结•• 9
2 环境友好型溶剂中的氯代反应研究••10
2.1环境友好型溶剂中氯代反应最佳反应条件的探索10
2.1.1结果与讨论 10
2.1.2 实验部分•• 14
2.1.2.1 TCCA的用量对反应收率的影响•14
2.1.2.2 反应的时间对反应收率的影响•14
2.1.2.3 氯化胆碱的用量对反应收率的影响15
2.1.2.4 乙酸乙酯的用量对反应收率的影响15
2.2 环境友好型溶剂中氯代反应普适性的探索••16
2.2.1 结果与讨论 17
2.2.2 实验部分•• 18
2.2.2.1 苯乙酮的二氯代反应 18
2.2.2.2 对氯苯乙酮的二氯代反应•• 19
2.2.2.3 对溴苯乙酮的二氯代反应•• 19
2.2.2.4 对氟苯乙酮的二氯代反应•• 20
2.2.2.5 对甲基苯乙酮的二氯代反应 20
2.2.2.6 对硝基苯乙酮的二氯代反应 21