Glycerol carbonate structuring in aqueous solutions as inferred from mutual diffusion coefficient, density and viscosity measurements in the temperature range 283.15-313.15 K

Glycerol Carbonate (4-hydroxymethyl-2-oxo-1,3-dioxolane, GC) is an emerging green reactant for many organic chemistry applications. GC popularity stems from its high reactivity, which makes it attractive for many chemical transformations and for its easy synthesis from glycerol, a byproduct of biodiesel produc-tion. While extensive literature covers the synthesis and chemical reactivity of GC, its transport proper-ties are poorly studied, especially in water. Here, we measured for the first time the diffusion coefficient of GC in water in the temperature range 283.15-313.15 K and for concentrations up to 0.1 M. By taking advantage of the Taylor Dispersion Analysis (TDA) we found D-0 = 9.53 +/- 0.06 x 10(-10) m(2)/s at 298.15 K and an activation energy for the diffusion process E-a = 3.74 +/- 0.09 kcal/mol. Density and dynamic viscosity were also measured in the same temperature interval to calculate the hydrodynamic radius of GC. Experimental data helped in assessing the structure of GC aggregates formed in aqueous solutions and provided an estimation of the equilibrium constant for the dimer formation. Our findings can be useful for studying the fate of GC in the environment and to improve its use for applications in aqueous media. (C) 2022 Elsevier B.V. All rights reserved.

Automated summary

Glycerol Carbonate (GC) is an emerging green reactant with high reactivity and easy synthesis from glycerol, making it attractive for many organic chemistry applications. However, the transport properties of GC, especially the diffusion coefficient in water, have been poorly studied. In this study, the diffusion coefficient of GC in water was measured for the first time, and its hydrodynamic radius and aggregate structure in aqueous solutions were investigated. The findings contribute to the understanding of GC's fate in the environment and its potential applications in aqueous media.