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Experimental and Modeling Studies on the Solubility of 2-Chloro-N-(4-methylphenyl)propanamide (S1) in Binary Ethyl Acetate + Hexane, Toluene + Hexane, Acetone + Hexane, and Butanone + Hexane Solvent Mixtures Using Polythermal Method

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Synthesis and Solid State Pharmaceutical Centre (SSPC), School of Chemical and Bioprocess Engineering, University College Dublin, Belfield, Dublin 4, Ireland
APC Ltd, Cherrywood Business Park, Loughlinstown, Co Dublin, Ireland
*Tel.: +353 1 7162815; Fax: +353 1 7161177; E-mail: [email protected]
Cite this: J. Chem. Eng. Data 2017, 62, 10, 3193–3205
Publication Date (Web):September 8, 2017
Copyright © 2017 American Chemical Society

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    The solubility of 2-chloro-N-(4-methylphenyl)propanamide (S1) in ethyl acetate + hexane mixtures between the temperatures of 273.43 to 327.67 K, in toluene + hexane mixtures from 273.24 to 331.62 K, in acetone + hexane mixtures from 269.81 to 318.8 butanone + hexane mixtures between 267.10 and 322.92 were determined using the polythermal method. In situ focused beam reflectance measurement (FBRM) was used to characterize the dissolution properties and to provide S1’s saturation temperature profile as a function of concentration. It was demonstrated that the solubility of S1 increases with increasing temperature at constant solvent composition. The experimental solubility data were correlated using Apelblat, λh, and phase equilibria with NRTL (nonrandom two liquid) model equations, and the predicted solubility data obtained agree sufficiently with the experimental data based on the relative deviation (RD%) and average relative deviation (ARD%) values. The Apelblat and λh model equation provides a convenient operational model of engineering interest to calculate the solubility of S1 quickly and easily, although it does not take the solvent composition into account, therefore needing separate parameters for each different solvent compositions. Therefore, the phase equilibria with NRTL model equation is used to provide a more comprehensive model that illustrates the effect of solvent composition on the solubility more apparently. One general set of NRTL parameters has the capability of describing all solvent compositions. Additionally, the melting temperature, Tm and the molar fusion enthalpy, ΔfusH, (394.83 K and 26.77 kJ mol–1 respectively) of S1 were determined by differential scanning calorimetry (DSC).

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.7b00288.

    • Graphs showing the solubility data of S1 in ethyl acetate + hexane, toluene + hexane, acetone + hexane, and butanone + hexane solvent mixtures, correlated using the Apelblat, λh, and phase equilibria with NRTL model equations (PDF)

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