Synthesis and Properties of 2-Halo-1,3-diether-propanes: Diversifying the Range of Functionality in Glycerol-Derived Compounds

Abstract

Synthesis of value-added chemicals from glycerol derivatives has been of real interest due to the excess volumes of glycerol resulting from biofuel production. Previously, we have demonstrated the controlled synthesis of symmetric and asymmetric 1,3-diether-2-propanol compounds bearing glycerol skeletons, which, in addition to potential applications as CO2 capture solvents, are also versatile intermediates for a number of further chemical transformations. Here, we demonstrate the conversion of these compounds to corresponding 2-halo-1,3-diethers as a means of further diversifying the range and properties of glycerol-derived compounds. Thermophysical properties of these compounds (density, molar volume, and viscosity) were measured over a temperature range of 20–80 °C. The experimental work was augmented by theoretical calculations of density, viscosity, vapor pressure, and dipole moment for each of the synthsized compounds as well as additional species with similar structures that have not yet been synthesized. The data obtained in this work provide a useful guide for valorization of glycerol in the form of new solvents and building blocks for value-added chemicals.