THE CONVERSION OF OPTICALLY ACTIVE LACTIC ACID TO THE CORRESPONDING PROPYLENE GLYCOL
THE CONVERSION OF OPTICALLY ACTIVE LACTIC ACID TO THE CORRESPONDING PROPYLENE GLYCOL
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光学活性乳酸转化为相应的丙二醇
DOI：
10.1016/s0021-9258(18)84750-0
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发表时间：
--
影响因子：
4.8
通讯作者：
H. Haller
中科院分区：
文献类型：
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作者：
P. Levene;H. Haller
之前的通信1涉及通过左旋-l-氨基-2-羟基丙烷的中间步骤将左旋-/3-氧丁酸转化为左旋丙二醇。P. Karrer和W. Klarer独立地、同时地报告了相同的结果。2在我们发表第一篇论文时，我们遗憾地忽略了E. Abderhalden和E. Eichwald3更早的一篇论文，他们从右旋-l-氨基-2-氯丙烷开始，得出左旋-/3-羟基丁酸。根据Abderhalden的说法，右旋丙二醇会生成左旋/3-羟基丁酸。在我们的实验以及Karrer和他的同事的实验中，/3-羟基丁酸和由它得到的丙二醇沿同一方向旋转。目前正在调查造成差异的原因。本通讯载有关于左旋乳酸转化为左旋丙二醇的报告。以乳酸酯为原料，采用金属还原法制备丙二醇。用本实验室改良的布沃法提取钠。按照原来的方法将a-羟基酸酯转化为相应的乙二醇的努力没有成功。在我们实验室所遵循的程序下，确实发生了所需方向的还原，尽管乙二醇的产率非常小。对丙二醇进行了一次正确的分析；在另一种情况下，该物质所含的碳比理论上乙二醇所要求的要高。然而，乙二醇很容易以其二氨基甲酸酯的形式被识别出来
A previous communication 1 dealt with the conversion of levo-/3-oxybutyric acid into levo-propylene glycol through the intermediary step of levo-l-amino-2-hydroxypropane. Independently and simultaneously, identical results were reported by P. Karrer and W. Klarer. 2 At the time of our first publication we overlooked, to our regret, an earlier publication by E. Abderhalden and E. Eichwald3 who, starting from dextro-l-amino-2-chloropropane arrived at levo-/3-hydroxybutyric acid. According to Abderhalden, dextro-propylene glycol leads to levo-/3-hydroxybutyric acid. In our experiments as well as in those of Karrer and his coworker,/3-hydroxybutyric acid and the propylene glycol obtained from it rotated in the same direction. The causes of the discrepancy are now under investigation. The present communication contains a report on the conversion of levo-Iactic acid into levo-propylene glycol. The propylene glycol was obtained on reduction of the ester of lactic acid by means of metallic. sodium by the method of Bouveault as modified in this laboratory. Efforts at converting esters of a-hydroxy acids into the corresponding glycols according to the original method were not successful. Under the procedures followed in our laboratory the reduction in the desired direction did take place although the yield of the glycol was very small. The product analyzed correctly for propylene glycol in one instance; in another, the substance contained a higher percentage of carbon than is required by theory for the glycol. However, the glycol was readily identified in the form of its diurethane