Quantitative analysis and comparison of the physical properties of O-alkyl and S-alkyl monoethers of glycerol

A homologous series (C(10), C(12), C(14), C(16), C(18)) of synthetic O-alkyl and S-alkyl ethers of glycerol was analyzed by gas-liquid chromatography (GLC) and thin-layer chromatography (TLC), and examined by IR and n.m.r. spectroscopy; the physical properties of the O-alkyl and S-alkyl ethers were compared. Isopropylidene derivatives of the glycerol ethers and thioethers were quantitatively analyzed by GLC on polar and nonpolar liquid phases. On a medium polar liquid phase (ethylene glycol succinate), mixtures of the O-alkyl and S-alkyl ethers were completely resolved. Isopropylidene derivatives of glycerol ethers and of thioethers could be separated as classes (though not into individual homologues) by TLC. O-hexadecyl and S-hexadecyl ethers of glycerol are easily distinguished by IR and n.m.r. spectroscopy.