Efficient 16O-18O isotope exchange reactions of carbonyl compounds in aqueous organic solvents catalyzed by acidic resin
Efficient 16O-18O isotope exchange reactions of carbonyl compounds in aqueous organic solvents catalyzed by acidic resin
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DOI：
10.1016/j.cej.2010.10.052
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发表时间：
2011-03-01
影响因子：
15.1
通讯作者：
Miyazawa, Akira
中科院分区：
文献类型：
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作者：
Kawanishi, Yuji;Suzuki, Yasuzo;Miyazawa, Akira
稳定同位素标记分子的简便制备方法在分析标准化学品、生物化学和医学应用中有着广泛的需求。以Dowex 50 WX 4树脂为固体酸催化剂，在毛细管柱反应器中进行了羰基O-16-O-18同位素交换反应，得到了高纯度的同位素。因此，羰基-O-18化合物如苯甲醛-O-18、3-/4-硝基苯甲醛-O-18、1-萘甲醛-O-18和苯乙酮-O-18以大于95 at.%在中等温度下，在51 s的停留时间内，在稳定流动操作下的纯度。当将羰基-O-16化合物的乙腈溶液注入反应器中时，加入100 eq. mol的（H2O）-O-18。最大产物同位素比z（max）已被公式化为z（max）=（x（0 y）+ z（0））/（y + 1），其中x（0）和z（0）分别是作为反应物的H2O和羰基的同位素比，y是[[H2O]/[羰基]的摩尔比。实际同位素比（z）与理论z（max）的实现比达到0.98或更高。(C)2010 Elsevier B. V.保留所有权利。
A facile preparative method for stable isotope labeled molecules is widely demanded in analytical standard chemicals, biochemical science and medical applications. A rapid O-16-O-18 isotope exchange reaction of carbonyl group to attain a high isotopic purity has been demonstrated using a capillary column reactor packed with Dowex 50WX4 resin as a solid acid catalyst. Thus, carbonyl-O-18 compounds such as benzaldehyde-O-18, 3-/4-nitrobenzaldehydes-O-18, 1-naphthaldehyde-O-18 and acetophenone-O-18 were produced with more than 95 at.% purity under the stable flow operation at a moderate temperature within a residence time of 51 s. when the acetonitrile solutions of carbonyl-O-16 compounds were injected to the reactor with 100 eq. mol of (H2O)-O-18. The maximal product isotopic ratio, z(max), has been formularized as z(max) = (x(0y) + z(0))/(y + 1), where x(0) and z(0) are isotopic ratio of H2O and carbonyl group as reactants, respectively, and y is the molar ratio [[H2O]/[carbonyl group]. The achievement ratio of the actual isotopic ratio (z) to theoretical z(max) has reached 0.98 or higher. (C) 2010 Elsevier B.V. All rights reserved.