摘要：近年来，随着人类社会越来越重视环境保护，人们开始从绿色化学的理念出发来研究有机物的取代反应，对许多酮类化合物开始采用绿色卤化试剂和绿色卤化方法，尤其是对改进工业生产方面的研究方法被人们越来越提倡。α位一氯代化合物是有机化学中的一类非常重要的羰基化合物，它是一种反应活性较高的合成中间体。虽然现在有许多合成此类化合物的方法，但是这些方法都有缺点，比如说反应试剂具有毒性，会对设备造成腐蚀等，因此不利于生产、运输等，不符合绿色化学理念。由此可见，研究温和条件下苯乙酮类化合物α位一氯代反应是很有必要的。

本论文以一定量的苯乙酮类化合物为底物，用醇类化合物作为反应溶剂，加入价格低廉，低毒的强氧化剂三氯异氰尿酸（TCCA，trichloroisocyanuric acid）进行氯代反应，调整苯乙酮类化合物与TCCA之间的比例，溶剂的种类和用量,优化反应时间和反应温度，尝试研究出高效、快速、绿色的α位一氯代化合物的合成路线，且能够较多的获得具有高选择性的α位一氯代化合物。通过实验发现：当苯乙酮与TCCA的摩尔比为1:2/3，使用20 mL甲醇作为溶剂，在室温下反应两小时，所获得的实际产量最大，为1.34 g，产率高达86.7%。

关键词： α位一氯代物；甲醇溶剂；温和条件；绿色化学

α -Monochlorination of acetophenone compounds under mild conditions

Abstract: In recent years, with the attention of the human society to environmental protection, the substitution reaction of organic compounds from the idea of green chemistry was studied. The green halogenation reagents of various ketones and their green halogenation methods, especially the industrial extension methods, have also been paid attention to. α-monochlorinated compounds are one of the most important carbonyl compounds in organic chemistry. And it is a synthetic intermediate with high reaction activity. Although there were many methods to synthesize these compounds, these methods had shortcomings. For example, some reaction reagents were toxic, and the equipments may be corroded. So they were not good for production, transportation and they didn’t conform to the idea of green chemistry. In this situation, it is necessary to study α-mono-chlorination of acetophenones under mild conditions.

In this paper, a certain amount of acetophenones was used as the substrate, alcohol compound was used as the reaction solvent. And trichloroisocyanuric acid (TCCA) which was low cost and low toxic oxidant was added to the chlorination reaction. Through adjusting the ratio of acetophenones to TCCA and the kind and the amount of the solvent and optimizing the reaction time and the reaction temperature, the synthesis route of high efficient, rapid and green α-monochlorinated compounds could be studied, and highly selective α-monochlorinated compounds could be obtained as much as possible. According to experiments, it was found that when the molar ratio of acetophenones to TCCA was 1:2/3, 20 mL of methanol was used as solvent, and the reaction was carried out at room temperature for two hours, the actual yield was the largest, which was 1.34 g and the productivity was up to 86.7%.

Key words: α-monochlorinated compounds; methanol solvent; mild conditions; green chemistry

目  录

1 绪论 1

1.1 温和条件下反应的相关研究 1

1.1.1含氧化合物在温和条件下的反应 1

1.1.1.1 含氧化合物在温和条件下的加成反应 1

1.1.1.2 含氧化合物在温和条件下的取代反应 1

1.1.2 含氮化合物在温和条件下的反应 3

1.1.3 卤代烷烃在温和条件下的反应 3

1.2 醇类化合物作为反应溶剂的相关研究 4

1.2.1 醇类化合物作为反应溶剂的取代反应 4

1.2.2 醇类化合物作为反应溶剂的加成反应 5

1.2.3 醇类化合物作为反应溶剂的其他反应 6