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

• Main Authors: Randall Wood, Claude Piantadosi, Fred Snyder
• Format: Article
• Language: English
• Published: Elsevier 1969-07-01
• Series: Journal of Lipid Research
• Subjects: glycerol 1-ethers; 1-thioethers; isopropylidene derivatives; gas-liquid chromatography with sulfur filter; thin-layer chromatography; IR spectroscopy
• Online Access: http://www.sciencedirect.com/science/article/pii/S0022227520430627
• ISSN: 0022-2275

A homologous series (C10, C12, C14, C16, C18) 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.