固定化手性咪唑鎓盐离子液体的合成及表征
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摘要
离子液体越来越广泛地应用于有机合成、分子催化、电化学以及分离等领域,手性离子液体的手性识别能力、固定化离子液体良好的工业化应用前景已受到人们的广泛关注。咪唑鎓盐离子液体是目前最重要的离子液体之一,我们以L-丙氨酸为起始原料,通过与甲醛、乙二醛及氨水缩合制得了L-2-(1-咪唑基)丙酸,再与甲醇进行酯化反应制得了L-2-(1-咪唑基)丙酸甲酯--一种制备手性咪唑鎓盐离子液体的前体,用两种方法制得了以MCM-41分子筛为载体的固定化手性咪唑鎓盐离子液体,优化了制备L-2-(1-咪唑基)丙酸甲酯的工艺条件,用元素分析、IR、NMR、MS、DSC-TG等手段对各阶段反应产物的结构进行了表征。
建立了一种切实可行的离子液体的固定化方法,充分利用了烷氧基硅烷的结构特点,巧妙地将离子液体的制备与固定化结合起来,且离子液体手性中心的构型不会因固定化过程而改变。
首次制得了以MCM-41分子筛为载体的固定化手性咪唑鎓盐离子液体,所制备的固定化离子液体具有良好的稳定性。
Room-temperature Ionic Liquids (RTILs) are widely used in organosynthesis, catalysis, electrochemistry, separation and so on. Chiral Ionic Liquids (CILs) which have good chiral recognition ability and Supported Ionic Liquids (SILs) which have potential application have caused public concern over the recent years. Imidazolium salts ILs are one of the most ILs. N-subsitituted imidazate is synthesized by L-lactamine with formaldehyde, glyoxal and ammonia. Then, it is esterified with methanol. The MCM-41 supported imidazolium ILs are synthesized by two methods. The preparation conditions of L-1-(imidazoleyl) propanote are selected or confirmed through repetitious experiments. The structure of productions is characterized by elementary analysis, IR, NMR, MS and DSC-TG.
The achievable immobilizated method in which the structural feature of alkoxylsilane is taken advantage and the synthesis of ILs is integrated with immobilisation process has been developed. Moreover, the configuration of CILs will not be changed in immobilization process.
The MCM-41 supported immodazolium ILs has been synthesized for the first time. The result shows that the SILs have better thermal stability.
建立了一种切实可行的离子液体的固定化方法,充分利用了烷氧基硅烷的结构特点,巧妙地将离子液体的制备与固定化结合起来,且离子液体手性中心的构型不会因固定化过程而改变。
首次制得了以MCM-41分子筛为载体的固定化手性咪唑鎓盐离子液体,所制备的固定化离子液体具有良好的稳定性。
Room-temperature Ionic Liquids (RTILs) are widely used in organosynthesis, catalysis, electrochemistry, separation and so on. Chiral Ionic Liquids (CILs) which have good chiral recognition ability and Supported Ionic Liquids (SILs) which have potential application have caused public concern over the recent years. Imidazolium salts ILs are one of the most ILs. N-subsitituted imidazate is synthesized by L-lactamine with formaldehyde, glyoxal and ammonia. Then, it is esterified with methanol. The MCM-41 supported imidazolium ILs are synthesized by two methods. The preparation conditions of L-1-(imidazoleyl) propanote are selected or confirmed through repetitious experiments. The structure of productions is characterized by elementary analysis, IR, NMR, MS and DSC-TG.
The achievable immobilizated method in which the structural feature of alkoxylsilane is taken advantage and the synthesis of ILs is integrated with immobilisation process has been developed. Moreover, the configuration of CILs will not be changed in immobilization process.
The MCM-41 supported immodazolium ILs has been synthesized for the first time. The result shows that the SILs have better thermal stability.
引文
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[25]黄德英,管国锋,万辉等.疏水性咪唑类离子液体的水浴微波合成.南京工业大学学报,2007,29(3):47-50
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[32]K.Fukumoto,M.Yoshizawa,H.Ohno.Room Temperature Ionic Liquids from 20Natural Amino Acids.J.Am.Chem.Soc,2005,127:2398-2399
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