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Thermodynamic properties of paracetamol impurities 4-nitrophenol and 4'-chloroacetanilide and the impact of such impurities on the crystallisation of paracetamol from solution

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dc.contributor.author Steendam, René R.E.
dc.contributor.author Keshavarz, Leila
dc.contributor.author de Souza, Brian P.
dc.contributor.author Frawley, Patrick J.
dc.date.accessioned 2019-03-22T09:05:02Z
dc.date.issued 2019
dc.identifier.uri http://hdl.handle.net/10344/7712
dc.description peer-reviewed en_US
dc.description The full text of this article will not be available in ULIR until the embargo expires on the 02/02/2019
dc.description.abstract The impact of structurally-related additives and impurities on active pharmaceutical ingredients is an essential yet poorly understood area. This work describes the characterisation of temperature-dependent solid-liquid properties of 4-nitrophenol and 4′chloroacetanilide in four different alcohols and their effect as impurities on the crystallisation of paracetamol. The solubility of 4-nitrophenol appeared to be significantly higher than paracetamol whereas the solubility of 4′chloroacetanilide was lower than paracetamol. The solubility difference between the impurities could be rationalised based on their molecular structure and hydrogen bonding interactions. The solubility data was modelled using empirical and thermodynamic models. Recrystallisation of paracetamol from solutions containing the highly soluble 4-nitrophenol impurity resulted in small uniformly sized high purity paracetamol crystals whereas the presence of the poorly soluble 4′chloroacetanilide impurity induced the formation of large needle shaped crystals of paracetamol. These differences in crystallisation are a consequence of the solubility difference and the different functional groups of paracetamol and its impurities. Overall this study serves as fundamental information for the development of crystallisation approaches for the purification of paracetamol from its main impurities. en_US
dc.language.iso eng en_US
dc.publisher Elsevier en_US
dc.relation 12RC2275 en_US
dc.relation.ispartofseries The Journal of Chemical Thermodynamics;133, pp. 85-92
dc.relation.uri https://doi.org/10.1016/j.jct.2019.02.004
dc.rights This is the author’s version of a work that was accepted for publication in The Journal of Chemical Thermodynamics. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in The Journal of Chemical Thermodynamics, 2019, 133, pp. 85-92, https://doi.org/10.1016/j.jct.2019.02.004 en_US
dc.subject crystallisation en_US
dc.subject solubility en_US
dc.subject impurity en_US
dc.subject additive en_US
dc.subject morphology en_US
dc.subject thermodynamic modelling en_US
dc.title Thermodynamic properties of paracetamol impurities 4-nitrophenol and 4'-chloroacetanilide and the impact of such impurities on the crystallisation of paracetamol from solution 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.jct.2019.02.004
dc.contributor.sponsor SFI en_US
dc.relation.projectid 12/RC/2275 en_US
dc.date.embargoEndDate 2021-02-02
dc.embargo.terms 2021-02-02 en_US
dc.rights.accessrights info:eu-repo/semantics/embargoedAccess en_US


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