ガラス毛細管カラムガスクロマトグラフィーによるケトン類ジアステレオマーの分離

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Diastereoisomeric ketals of ketones were resolved by gas chromatography on a glass capillary column. First, glass capillary(25 m long, 0.25 mm i.d.) was etched with dry hydrogen chloride at 230°C for 24 hours. After etched, chromic-sulfuric acid was passed through this capillary and washed with water and methanol. Glass capillary was coated with 0.1 ml of 15% (w/v) NPGS/methylene chloride solution containing 0.2% (w/v) benzyltriphenylphosphonium chloride by the dynamic coating method with nitrogen pressure at a linear coating velocity of 1 cm/sec. After the solution had passed through the column, nitrogen pressure was maintained for about 5 hours to dry the solvent off. The column was then conditioned for 15 hours at 210°C. This column showed 58, 000 of HETP for diastereoiscmeric 3, 3, 5-trimethylcyclohexanone(Table I, 1st peak) without significant loss of efficiency after 100 hours of use at 190210°C. Ketalic diastereoisomers were obtained by reacting each ketone with (+)-dimethyl tartrate or (+)-2, 3-butanediol in Dean-Stark apparatus. When using (+)-dimethyl tartrate as a resolving reagent, sec-butylmethylketone, 3-methylcyclohexanone and 3, 3, 5-trimethylcyclohexanone were almost completely resolved and 2-methylcyclohexanone was partially resolved. And 2, 4, 4-trimethylcyclopentanone remained unresolved. When using (+)-2, 3-butanediol, however, 3-methylcyclohexanone, 2, 4, 4-trimethylcyclopentanone and 3, 3, 5-trimethylcyclohexanone were almost resolved, sec-butylmethylketone and 2-methylcyclohexanone were not resolved at all. Diastereoisomeric ketals from (+)-dimethyl tartrate have greater-Δ(ΔG°) than from (+)-2, 3-butanediol except 2, 4, 4-trimethylcyclopentanone.
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ガラス毛細管カラムガスクロマトグラフィーによるケトン類ジアステレオマーの分離

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