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de Souza, B;Keshavarz, L;Steendam, RRE;Dennehy, OC;Lynch, D;Collins, SG;Moynihan, HA;Maguire, AR;Frawley, PJ
Journal Of Chemical And Engineering Data
Solubility Measurement and Thermodynamic Modeling of N-(4-Methylphenyl-Z-3-chloro-2-(phenylthio)propenamide in 12 Pure Solvents at Temperatures Ranging from 278.15 to 318.15 K
WOS: 7 ()
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alpha-Thio-beta-chloroacrylamides are of considerable synthetic utility due to their versatile reactivity profile enabling a diverse range of useful transformations. Availability of accurate and extensive solubility data and models is a prerequisite for advanced process optimization of such valuable pure synthetic intermediate compounds, in particular facilitating their isolation with a high degree of efficiency and control. As an illustrative example the solubility of one such derivative, N-(4-methylphenyl-Z-3-chloro-2-(phenylthio)propenamide (Z-1), is described in the present work. Solubility data is reported in 12 pure solvents specifically selected for their potential utility in synthesis and isolation at scale. Solubility data are determined using the gravimetric method across a range of temperatures T=(278.15 to 318.15) K under pressure of 0.1 MPa. On a molar basis, the solubility of Z-1 at temperature T = 298.1S K was observed to follow the order: tetrahydrofuran > 1,2-dichloroethane > 2-methyltetrahydrofuran > butanone > acetone > ethyl acetate > methyl acetate > toluene > tert-butyl methyl ether > acetonitrile > 2-propanol > 2-methyl-2-butanol. The experimental solubility data were correlated by the modified Apelblat, Margules, Van-Laar, Wilson, and nonrandom two-liquid (NRTL) models. The NRTL model was found to result in the lowest error for 8 of the 12 solvents tested. In the case of acetonitrile, the Wilson model had a slightly lower mean square error of 3.52 x 10(-4) while for methyl acetate and 1,2-dichloroethane the Van-Laar model had the smallest mean square error of 1.47 x 10(-3) and 3.54 x 10(-4), respectively. The provision of solubility data and models for such a prized and versatile compound will assist with further development of continuous isolation strategies.
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