Identification of a Reaction By-Product in the Synthesis of Tetradecylchloride.

In the synthesis of tetradecyl chloride from tetradecyl alcohol and phosphorus pentachloride, an undesired white precipitate was observed to form with the product. After purification of the product and isolation of the by-product these materials we characterized by infrared and NMR spectroscopy. 1 H and 31 P NMR as well as 31 P decoupled proton spectra were obtained. These data proved that some protons were spin-coupled to a phosphorus nucleus in the by-product sample. From these data we were able to deduce that the by-product is possibly an amphipathic salt containing phosphorus and a tetradecyl alkyl group. The by-product structure and supporting spectral data will be presented