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摘要：α, α-二氯代苯乙酮类化合物作为一类重要的有机合成中间体，因其结构特殊，能够发生多种有机化学反应，而受到了越来越多的关注。但目前，虽然合成此类化合物方法有很多种，但是这些方法存在着一定的缺陷——不仅不易操作，并且合成所需使用的试剂的毒性通常很强。而近年来，由于对环境保护的关注度越来越高，因而实行绿色化学日趋紧迫。所以在这个大时代的背景下，利用新配制的低共熔物的特殊酸性，从而希望可以研发出简单、高效的α, α-二氯代反应，并开发出α, α-二氯代苯乙酮类化合物的绿色合成路线。论文以苄基三乙基氯化铵与对甲苯磺酸形成低共熔物，以此作为反应介质，主要考察在此低共熔物中的α, α-二氯代反应结果，通过调整各种反应物的比例，希望发展出简单、高效的α,α-二氯代反应，并应用于α, α-二氯代苯乙酮类化合物的合成。除此之外，本文还考察了从α, α-二溴代苯乙酮类化合物进行卤素交换得到α, α-二氯代苯乙酮类化合物的方法。8599
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关键词：低共熔物；α, α-二氯代苯乙酮；三氯异氰脲酸；卤素交换。
Simple and Efficient Green Synthesis of the α,α-Dichlorinated Acetophenones
Abstract: As a kind of important organic intermediates, α,α-dichlorinated acetophenones can participate in a variety of organic chemistry reaction because of its special structure, which has drawn more and more attentions. Currently there are large numbers of methods of preparing of these compounds, nevertheless, that have certain drawbacks. These methods are difficult to manipulate and high toxic for requisite reagent. Recently, with the high emphasis on environmental protection, green chemistry is becoming increasingly urgent. According to the requires of times, therefore, recently prepared DES (Deep Eutectic Solvent), from special acidity, has been utilized to develop a simple and efficient green synthesis of the α,α-dichlorinated acetophenones. In this thesis, TEBA (Triethylbenzylammonium) and p-toluenesulfonic acid were used for DES, the medium of the reaction, with which the reaction result of this synthesis of the α,α-dichlorinated acetophenones were studied. .Most proportions of reactant were adjusted to obtain an excellent yield of α,α-dichlorinated acetophenones, as well as other α,α-dichlorinated acetophenones compounds. Furthermore, in this thesis, the method of α,α-dichlorinated acetophenones from α,α-dibrominated acetophenones through halogen-exchange reaction was also studied.
Key words: DES; α,α-dichlorinated acetophenones; TCCA ; halogen-exchange reaction.
目录
1 绪论 1
1.1低共熔物的性质与用途 1
1.1.1 低共熔物的性质 1
1.1.1.1 低共熔物的定义 1
1.1.1.2 低共熔物的性质 1
1.1.1.3 低共熔点 1
1.1.2 低共熔物的用途 2
1.1.2.1 熔铸炸药中低共熔物的应用 2
1.1.2.2 储热材料中低共熔物的应用 3
1.1.2.3 建筑围护结构中低共熔物的运用 4
1.1.2.4 低共熔物在其他方面的运用 4
1.2低共熔物参与的绿色有机反应 5
1.3 绿色有机氧化反应 6
2 α,α-二氯代苯乙酮类化合物在低共熔物中的绿色合成 7
2.1 低共熔物中的α, α-二氯代反应最佳条件探索 7
2.1.1 结果与讨论 7
2.1.2 实验部分 10
2.2 各种α, α二氯代苯乙酮类化合物的合成 12