Antisolvent effect on the crystallization of fosfomycin phenylethylamine by acetone: Solubility measurement and thermodynamic mechanism analysis |
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| Authors: | Bingwen Long Shijie Zhu Yigang Ding |
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| Affiliation: | Key Laboratory for Green Chemical Process of Ministry of Education, Hubei Key Laboratory for Novel Reactor and Green Chemical Technology, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, China |
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| Abstract: | Antisolvent crystallization of fosfomycin phenylethylamin (FPEA) by acetone is demonstrated by measuring its solubility in binary solvents of (ethanol + acetone) and (water + acetone) at 293.15 K. The solubility (g/g) of FPEA always decreased with the increase of acetone composition and correlations were proposed to sufficiently represent the data. Excess solubilities (mole fraction) of FPEA were always positive with maximum and well correlated by the simplified-modified-Wilson equation. Effects of various solvent properties on the solubility were analyzed by the solvatochromic KAT linear solvation energy relationship, which revealed the decrease of solvent's hydrogen bond donation ability should be the most essential characteristics of the antisolvent. Finally, by analyzing its surrounding solvent composition using the inverse Kirkwood–Buff integrals method, we found FPEA was preferentially solvated by water in acetone–water due to the strong acidic behavior of water, while, because of different competing interactions in acetone–ethanol, FPEA was preferentially solvated by acetone in ethanol-rich region while by ethanol in acetone-rich region. |
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| Keywords: | acetone antisolvent fosfomycin phenylethylamine preferential solvation solubility solvent property |
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