光学活性固定相を用いるガスクロマトグラフィーによるα-ハロカルボン酸光学異性体の分離

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Gas chromatographic separation of α-halocar-boxylic acid enantiomers with an optically active stationary phase. Naobumi Oi, Hajimu KITAHARA, Yoko INDA, Masao HORIBA and Tadashi Doi (Institute for Biological Science, Sumitomo Chemical Co., Ltd., 4-2-1, Takatsukasa, Takarazuka-shi, Hyogo) The gas chromatographic separation of enantiomers of a-halocarboxylic acid in the form of amide on a 40 m glass capillary column coated with N,N'-[2,4-(6-ethoxy-l,3,5-triazine)-diyl] bis (L-valyl-L-valyl-L-valine isopropyl ester) (OA-300) has been studied. The separation factor for various amides of a-bromo-β, β-dimethylbutyric acid enantiomers were 1.022〜1.034 at 180°C. Therefore, the structure of amine was not so effective for the separation of enantiomers. Eleven a-halocarboxylic acid hexyl amides were resolved into their antipodes with separation factors ranging from 1.020〜1.032 in the same chromatographic conditions. As the differences of separation factors were quite small inα-chloro-, bromo- and iodo-alkyl carboxylic acids, it was concluded that halogen atoms did not produce a notable effect on the enantiomeric separation. The peak of R-isomer of α-chloro andα-bromo-β, β-dimethylbutyric acid appeared prior to that of S-isomer in this stationary phase. Although this order is reverse to that of α-alkyl phenylacetic acid enantiomers on the same optically active stationary phase, the results are seemed to be reasonable considering the absolute configuration of these compounds. Because, the absolute configurations on the α-carbon atoms to the both carbonyl groups in the R-isomer ofα-haloalkyl carboxylic acid and the S-isomer ofα-alkyl phenylacetic acid are superimposable. (Received Nov. 15, 1980)
社団法人日本分析化学会の論文
1981-04-05

光学活性固定相を用いるガスクロマトグラフィーによるα-ハロカルボン酸光学異性体の分離

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