Solubility of Biocompounds 2,5-Furandicarboxylic Acid and 5-Formylfuran-2-Carboxylic Acid in Binary Solvent Mixtures of Water and 1,4-Dioxane

Abstract

The solubility of 2,5-furandicarboxylic acid (FDCA) and its synthetic intermediates (e.g., 5-formylfuran-2-carboxylic acid, FFCA) provides fundamental information for the preparation and purification of the value-added biocompound FDCA. We measured the solubility of FDCA and FFCA in binary water + 1,4-dioxane mixtures with different mixing ratios at 303.15 K–342.15 K. The obtained solubility values were correlated with the Jouyban-Acree-van’t Hoff model, and the preferential solvation theory was used to study the microscopic dissolution mechanism. The solubility of FDCA/FFCA increases with increasing temperature, and pure 1,4-dioxane dissolves more solutes than pure water. FFCA shows higher solubility than FDCA. In the binary solvent mixtures, the phenomenon of co-solvency exists for both FDCA and FFCA, i.e., at a 1,4-dioxane mole fraction of about 0.60, FDCA and FFCA dissolve the most. Acceptable mean percentage deviations (MPD) (5.5% and 6.9%) are obtained for FDCA and FFCA (Jouyban-Acree-van’t Hoff model). The calculated preferential solvation parameters show different dissolution mechanisms at different solvent compositions. When the 1,4-dioxane mole fraction is 0.17~0.62/0.63, FDCA/FFCA are preferentially solvated by 1,4-dioxane. Otherwise, they are preferentially solvated by water. A trend similar to the “co-solvency phenomenon” is observed in the differences in solubility of FFCA and FDCA. This study gives important guidance for the use of binary water and 1,4-dioxane solvents in practical FDCA purification.