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Thermodynamics of the enantiotropic pharmaceutical compound benzocaine and solubility in pure organic solvents

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Show simple item record Cheuk, Dominic Svärd, Michael Rasmuson, Åke C. 2020-11-05T11:30:09Z 2020-11-05T11:30:09Z 2020
dc.description peer-reviewed en_US
dc.description.abstract The thermodynamic relationship between FI and FII of ethyl 4-aminobenzoate (benzocaine) has been investigated. Slurry conversion experiments show that the transition temperature below which FI is stable is located between 302 K–303 K (29 °C–30 °C). The polymorphs FI and FII have been characterised by infrared spectroscopy (IR), Raman spectroscopy, transmission powder X-ray diffraction (XRPD) and differential scanning calorimetry (DSC). The isobaric solid state heat capacities have been measured by DSC. The quantitative thermodynamic stability relationship has been determined in a comprehensive thermodynamic analysis of the calorimetric data. The solubility of both polymorphs has been determined in eight pure organic solvents over the temperature range 278 K–323 K by a gravimetric method. The mole fraction solubility of benzocaine decreases in the order: 1,4-dioxane, acetone, ethyl acetate, chloroform, acetonitrile, methanol, n-butanol and toluene. Comparison with the determined activity of solid benzocaine forms shows that negative deviation from Raoult's law ideality is found in dioxane, acetone and ethyl acetate solutions, and positive deviation in solutions of the other investigated solvents. en_US
dc.language.iso eng en_US
dc.publisher Elsevier en_US
dc.relation.ispartofseries Journal of Pharmaceutical Sciences;109,pp. 3370-3377
dc.subject Solubility en_US
dc.subject Polymorphism en_US
dc.subject Crystallization en_US
dc.subject Thermodynamics en_US
dc.title Thermodynamics of the enantiotropic pharmaceutical compound benzocaine and solubility in pure organic solvents en_US
dc.type info:eu-repo/semantics/article en_US
dc.type.supercollection all_ul_research en_US
dc.type.supercollection ul_published_reviewed en_US
dc.identifier.doi 10.1016/j.xphs.2020.07.022
dc.contributor.sponsor Swedish Research Council en_US
dc.contributor.sponsor SFI en_US
dc.contributor.sponsor European Union (EU) en_US
dc.relation.projectid 2019-5059 en_US
dc.relation.projectid 12/RC/2275 en_US
dc.rights.accessrights info:eu-repo/semantics/openAccess en_US

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