Synthesis and Properties of Novel Glycerol-Derived Liquids with Dual Functional Groups: Nonsymmetric (E/Z)-Isomeric Mixtures of 1,3-Diether-2-Alkenes.

This study introduces the synthesis and detailed characterization of six novel nonsymmetric (E/Z)-isomeric mixtures of 1,3-diether-2-alkenes derived from precursors with a glycerol skeleton: 1-((3-butoxyallyl)oxy)heptane ([H, A, B]), 1-(2-methoxyethoxy)-5-methylhex-2-ene ([ME, A, IP]), 1-((3-(2-methoxyethoxy)prop-1-en-1-yl)oxy)butane ([ME, A, B]), ((3-isopropoxyprop-1-en-1-yl)oxy)benzene ([IP, A, Ph]), ((3-(2,2,2-trifluoroethoxy)prop-1-en-1-yl)oxy)benzene ([F, A, Ph]), and 1-(allyloxy)-3-(2,2,2-trifluoroethoxy)prop-1-ene ([F, A, A]). These compounds were synthesized via a three-step reaction starting from various glycidyl ethers, purified by fractional distillation and drying, and obtained with overall isolated yields of at least 60%. The ratio of isomer configurations (E:E:Z:Z) varied based on substituents R1 and R2. Thermophysical properties, including density, refractive index (RI), and viscosity, were evaluated at temperatures of 293.15 to 333.15 and 353.15 K. CO2 absorption capacity (Henry's constants) of compound [F, A, A] was assessed at temperatures of 303.15, 318.15, 333.15, and 348.15 K under CO2 pressures from 2 to 10 atm. Density, viscosity, vapor pressure, enthalpy of vaporization, and dipole moment were also calculated for each compound. Moreover, the nonsymmetric alkenes' C ═ C double bond was shown to readily react with thiols via thiol-ene coupling. The resulting thioether linkage exhibits high stability under physiological conditions, making these compounds promising intermediates for synthesizing more complex glycerol-based molecules.