Armstrong D W, Reid G L, Hilton M L, Chang C D
Department of Chemistry, University of Missouri-Rolla, Rolla, MO 65401, USA.
Environ Pollut. 1993;79(1):51-8. doi: 10.1016/0269-7491(93)90177-p.
A significant number of all organic chemicals that are released into the environment are racemic mixtures. Most environmental regulations and scientific environmental studies treat racemic mixtures as though they were single, pure compounds. This can lead to incorrect toxicological, distribution, degradation and other data. A series of new enantioselective chromatographic techniques have been developed that allow the facile separation and quantitation of chiral compounds of environmental importance. Nineteen racemic compounds that have been or currently are being released to the environment are resolved. These include: rodenticides--Warfarin, Coumachlor and Coumafuryl; insecticides--Crufomate, Bulan, Fonofos, Mitotane; insect repellent--Ethohexadiol; herbicides and fungicides--Ancymidol, Silvex, Napropamide, phenyl mercuric lactate, 2-[3-chlorophenoxy]propionamide, and 2-chloropropionic acid; and halocarbons-1,2-dichloropropane, 2-bromo-1-chloropropane, 1,2-dibromo-3-chloropropane, 2,3-dichlorobutane and alpha-1,2,3,4,5,6-hexachlorocyclohexane. Several examples are given to illustrate the importance of enantioselective measurements of these and other compounds. Choosing the proper chromatographic technique and chiral stationary phase based on analyte structure is also discussed.
释放到环境中的所有有机化学品中有相当一部分是外消旋混合物。大多数环境法规和环境科学研究将外消旋混合物视为单一的纯化合物。这可能导致毒理学、分布、降解及其他数据出现错误。现已开发出一系列新的对映体选择性色谱技术,可轻松分离和定量具有环境重要性的手性化合物。已拆分出19种已释放或正在释放到环境中的外消旋化合物。这些包括:杀鼠剂——华法林、氯灭鼠灵和克灭鼠;杀虫剂——育畜磷、丙溴磷、地虫硫磷、米托坦;驱虫剂——2-乙基己二醇;除草剂和杀菌剂——嘧啶醇、2,4,5-涕丙酸、敌草胺、苯基汞乳酸盐、2-[3-氯苯氧基]丙酰胺和2-氯丙酸;以及卤代烃——1,2-二氯丙烷、2-溴-1-氯丙烷、1,2-二溴-3-氯丙烷、2,3-二氯丁烷和α-1,2,3,4,5,6-六氯环己烷。给出了几个例子来说明对这些化合物及其他化合物进行对映体选择性测量的重要性。还讨论了根据分析物结构选择合适的色谱技术和手性固定相的问题。