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Micellar Aqueous Oxidation System by Using New Amphiphilic Oxidants

使用新型两亲性氧化剂的胶束水氧化系统

基本信息

批准号：
12650835
负责人：
MASUYAMA Araki
金额：
$ 2.3万
依托单位：
Osaka University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2000
资助国家：
日本
起止时间：
2000 至 2001
项目状态：
已结题

项目摘要

1. New Oxidation System in Water by Using Amphiphilic HydroperoxideA unique amphiphilic α-alkoxyalkyl hydroperoxide (α-AHP) to act both as a micellar-forming reagent to solubilize organic substrates and as an oxidizing reagent was designed and prepared. DTA/TG analysis indicated that α-AHPs were stable in neat up to 100 ℃. Effective oxidation of benzyl sulfide to the corresponding sulfoxide in water has been achieved by using micellar α-AHP in the presence of a catalytic amount of MoO_2(acac)_2 under very mild conditions. This new oxidation system in water has a bright prospect of developing the new environmentally benign process.2. Ozonolyses of Alkenes in Micellar Aqueous SolutionsOzonolyses of a series of water-insoluble cyclopent-1 -enylbenzenes were carried out both in water and in micellar aqueous solutions. Ozonolyses of these substrates yielded the corresponding water-participation products (oxoaldehydes) and the corresponding water-nonparticipation products (sec-ozonides) exclusively. In water, secozonides were formed predominantly in the ozonolyses of all substrates. The product distribution in micellar systems drastically varied with the combination of substrate and surfactant. The difference in the solubilizing mode of substrates by micelles seems to be the key in determining the product distribution. This information will contribute to the promotion of application of this environmentally benign oxidation methodology to laboratory or industrial processes.

1.利用两亲性过氧化氢的新型水中氧化体系设计并制备了一种独特的两亲性α-烷氧烷基过氧化氢（α-AHP），既作为增溶有机底物的胶团形成剂，又作为氧化剂。DTA/TG分析表明，α-AHPs在100 ℃以下保持稳定。在温和条件下，以胶束α-AHP为催化剂，在催化量MoO_2（acac）_2存在下，实现了苯甲硫醚在水中的有效氧化。这种新的水相氧化体系在开发环境友好的新工艺方面具有良好的前景.烯烃在胶束水溶液中的臭氧化反应研究了一系列水不溶性环戊二烯基苯在水和胶束水溶液中的臭氧化反应。这些底物的臭氧分解产生了相应的水参与产品（oxoaldehyde）和相应的水非参与产品（sec-ozonides）排他。在水中，secozonides主要形成在所有基板的臭氧分解。产物在胶束体系中的分布随底物和表面活性剂的组合而变化。胶束对底物增溶方式的差异似乎是决定产物分布的关键。这些信息将有助于促进这种环境友好的氧化方法在实验室或工业过程中的应用。