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摘要：α-氯代苯乙酮类化合物是一类重要的有机合成中间体，引发了越来越多的关注。目前，虽然合成此类化合物方法有很多种，但是这些方法均存在着一定的缺陷——或不易操作，或合成过程中所需的试剂毒性强，且产物需多步提纯。随着环境保护的呼声越来越高，实行绿色化学迫在眉睫。无溶剂有机合成具有收率高、选择性强、操作简便、成本低及无环境污染等优点,是绿色化学的重要内容.
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本课题响应绿色化学的号召，在无溶剂环境中，利用TCCA(三氯异氰尿酸)进行苯乙酮类化合物的氯代反应，通过对酸性催化剂的筛选，寻找优化的反应条件，尝试通过调整各种反应物的比例使其得到较高的产率，从而研发出α-氯代苯乙酮类化合物的绿色合成路线。20382
本文的研究结果将为以后苯乙酮类化合物在无溶剂条件下的氯化提供理论和实验依据，为进一步开展绿色化学提供思路。
关键词：无溶剂体系；α-氯代苯乙酮；绿色化学
The Study of Chlorine Substitution Reaction of Acetophenones under Solvent-free Conditions
Abstract: As a kind of important organic intermediates， α-chlorinated acetophenones can participate in a variety of organic chemistry reaction ,which has drawn more and more attentions. Currently there are large numbers of methods of preparing of these compounds.However, most of which have certain drawbacks. These methods are difficult to manipulate and high toxic for requisite reagent. With the high emphasis on environmental protection, green chemistry is becoming increasingly urgent. Organic synthesis under solvent-free conditions with many advantages such as the excellent yields, operational simplicity and good selectivity, meet the requirements of green chemistry.
In this paper, by selecting TCCA ,chlorine substitution reaction of acetophenones is carried out under solvent-free conditions. Selecting different acidic catalyst to find optimal reaction conditions and most proportions of reactants were adjusted to obtain an excellent yield of products . Consecquently a greener synthetic pathways of α-chlorinated acetophenones and other α-chlorinateed acetophenones analogues is developed .
In conclusion, we have developed a simple, mild, inexpensive, environmentally friendly method for chlorine substitution reaction of acetophenones. The results will build a theoretical and experimental basis for chlorine substitution reaction of acetophenones under solvent-free conditions and provide new ideas for further development of green chemisty.
Key words: solvent-free conditions ; αchlorinated acetophenones; green chemisty
目录
1绪论 1
1.1 论文的意义与目的 1
1.2 选题研究现状及发展趋势 2
1.2.1 无溶剂反应的进展 2
1.2.2苯乙酮的氯代反应 5
2 无溶剂条件下TCCA与苯乙酮化合物的氯代反应 9
2.1引言 9
2.210%的稀硫酸为催化剂的苯乙酮氯代反应条件探索 9
2.2.1 引言 9
2.2.2结果与讨论 10
2.2.3 实验部分 12
2.3以10%的稀硫酸为催化剂的α氯代反应底物拓展 13
2.3.1 引言 13
2.3.2 结果与讨论 14
2.3.3 实验部分 16
2.4以对甲苯磺酸为催化剂的氯代反应最佳条件探索 20
2.4.1 引言 20
2.4.2结果与讨论 20
2.4.3 实验部分 23
2.5 以对甲苯磺酸为催化剂的氯代反应底物拓展 25
2.5.1 引言 25
2.5.2 结果与讨论 25