Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

ABSTRACT

-Thio--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 pre-requisite 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-3chloro-2-(phenylthio)propenamide (Z-1), is described in the present work. Solubility data is reported in twelve pure solvents specifically selected for their potential utility in synthesis and isolation at scale. Solubility data is 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=298.15 K was observed to follow the order: tetrahydrofuran greater than 1,2-dichloroethane greater than 2-methyltetrahydrofuran greater than butanone greater than acetone greater than ethyl acetate greater than methyl acetate greater than toluene greater than tert-butyl methyl ether greater than acetonitrile greater than 2-propanol greater than 2-methyl-2-butanol. The experimental solubility data were correlated by the modified Apelblat, Margules, Van-Laar, Wilson and NRTL models. The NRTL model was found to result in the lowest error for eight of the twelve solvents tested. In the case of acetonitrile, the Wilson model had a slightly lower mean square error of 3.52x10-4 while for methyl acetate and 1,2-dichloroethane the Van-Laar model had the smallest mean square error of 1.47x10-3 and 3.54x10-4 respectively. The provision of solubility data and models for such a prized and versatile compound will assist with further development of continuous isolation strategies.