Understanding the solubility behavior of 2,2′-bifuran-5,5′-dicarboxylic acid in different pure solvents

IF 2.8 3区工程技术 Q3 CHEMISTRY, PHYSICAL Fluid Phase Equilibria Pub Date : 2025-01-22 DOI:10.1016/j.fluid.2025.114355

Samir F. Castilla-Acevedo , Alvaro Pallais-Leclair , Diego T. Melfi , Pooja Bhalode , Berlyn Mellein , Aaron M. Scurto , Dionisios G. Vlachos , Alan M. Allgeier

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Abstract

The molecule 2,2′-bifuran-5,5′-dicarboxylic acid (BFDCA) has attracted significant attention due to its potential as a building block to form biorenewable polymers. However, there is no information available on the solubility of BFDCA in pure solvents, hindering the effective design for reaction, separation, and crystallization processes. The present work evaluated the solubility of BFDCA in eight different solvents at temperatures from 298.15 K to 363.15 K. On a mole fraction basis, the BFDCA solubility from high to low at 298.15 K followed the order: DMAc > DMSO > MeOH > 1-pentanol > 2-propanol > acetic acid > acetonitrile > H₂O. Additional solubility tests were performed in cyclohexane, acetone, and dichloromethane, but the equilibrium solute concentration was below the detection limit of the instrument in the range of temperatures studied. The sigma (σ) profile of BFDCA shows that this molecule is strongly polar and can behave as a donor and acceptor of hydrogen bonds. A higher screening charge density was found in the hydrogen bonding (HB) donor regions in BFDCA, which would favor the interaction with the solvents’ HB acceptor regions. Correlations between BFDCA solubility and solvent property parameters show that solvents’ HB acceptor propensity and total basicity play an important role in the solute solubility, which agrees with the findings from the σ profile of BFDCA and solvents and linear energy solvation relationships (LSER). However, the dipole moment, dielectric constant, cohesive energy density, and surface tension also influence the BFDCA solubility since the evaluated molecular descriptors are insufficient to explain the solubility behavior in some cases. The Apelblat equation and the NRTL activity coefficient model aptly described the experimentally observed solubility with model fitting, whereas the COnductor-like Screening MOdel for Real Solvents (COSMO-RS) method predicted qualitative trends.

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来源期刊

Fluid Phase Equilibria 工程技术-工程：化工

CiteScore

5.30

自引率

15.40%

发文量

223

审稿时长

53 days

期刊介绍： Fluid Phase Equilibria publishes high-quality papers dealing with experimental, theoretical, and applied research related to equilibrium and transport properties of fluids, solids, and interfaces. Subjects of interest include physical/phase and chemical equilibria; equilibrium and nonequilibrium thermophysical properties; fundamental thermodynamic relations; and stability. The systems central to the journal include pure substances and mixtures of organic and inorganic materials, including polymers, biochemicals, and surfactants with sufficient characterization of composition and purity for the results to be reproduced. Alloys are of interest only when thermodynamic studies are included, purely material studies will not be considered. In all cases, authors are expected to provide physical or chemical interpretations of the results. Experimental research can include measurements under all conditions of temperature, pressure, and composition, including critical and supercritical. Measurements are to be associated with systems and conditions of fundamental or applied interest, and may not be only a collection of routine data, such as physical property or solubility measurements at limited pressures and temperatures close to ambient, or surfactant studies focussed strictly on micellisation or micelle structure. Papers reporting common data must be accompanied by new physical insights and/or contemporary or new theory or techniques.