Extending the SAFT-γ Mie approach to model benzoic acid, diphenylamine, and mefenamic acid : solubility prediction and experimental measurement

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Febra, Sara A. and Bernet, Thomas and Mack, Corin and McGinty, John and Onyemelukwe, Iyke I. and Urwin, Stephanie J. and Sefcik, Jan and ter Horst, Joop H. and Adjiman, Claire S. and Jackson, George and Galindo, Amparo (2021) Extending the SAFT-γ Mie approach to model benzoic acid, diphenylamine, and mefenamic acid : solubility prediction and experimental measurement. Fluid Phase Equilibria, 540. 113002. ISSN 0378-3812 (https://doi.org/10.1016/j.fluid.2021.113002)

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Abstract

The prediction of the solubility of active pharmaceutical ingredients (APIs) is a significant challenge which is of importance in pharmaceutical applications and solvent selection. Here, we extend the table of group interactions (3 like interactions, 47 unlike interactions) of the SAFT-γ Mie group-contribution equation of state to model the phase behaviour and solubility of mefenamic acid, a nonsteroidal anti-inflammatory drug, in a range of solvents. In addition to mefenamic acid, we also consider its molecular synthons: benzoic acid and diphenylamine. New experimental solubility data are presented for the three molecules in a range of solvents, and three new SAFT-γ Mie functional groups are defined (aCCOOH, aCNHaC and CH 3CO) and characterised, together with their interactions with solvent groups. Literature data for the vapour pressure, single-phase density, saturation density, vapourisation enthalpy, bubble temperature, dew temperature, and bubble pressure are used to characterise the new group interactions. Solubility data are used to characterise the new group-group interactions only if there are no other experimental data available. The transferability and predictive accuracy of the new models are assessed by comparing the theoretical predictions with the experimental solubility data. Our comparison includes alcohols, ketones, and esters as families of solvents and mixed-solvent solubility predictions.

ORCID iDs

Febra, Sara A., Bernet, Thomas, Mack, Corin, McGinty, John ORCID logoORCID: https://orcid.org/0000-0002-8166-7266, Onyemelukwe, Iyke I., Urwin, Stephanie J. ORCID logoORCID: https://orcid.org/0000-0002-9092-0200, Sefcik, Jan ORCID logoORCID: https://orcid.org/0000-0002-7181-5122, ter Horst, Joop H. ORCID logoORCID: https://orcid.org/0000-0003-0118-2160, Adjiman, Claire S., Jackson, George and Galindo, Amparo;
CORE (COnnecting REpositories)