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Phase equilibria and thermodynamics of hydroxybenzoic acid isomers and salicylamide
KTH, School of Chemical Science and Engineering (CHE), Chemical Engineering and Technology, Transport Phenomena.
2005 (English)Licentiate thesis, comprehensive summary (Other scientific)
Place, publisher, year, edition, pages
Stockholm: KTH , 2005. , xii, 52 p.
Series
Trita-KET, ISSN 1104-3466 ; 217
Keyword [en]
Chemical engineering, salicylic acid, p-hydrozybenzoic acid, m-hydrozybenzoic acid
Keyword [sv]
Kemiteknik
National Category
Chemical Engineering
Identifiers
URN: urn:nbn:se:kth:diva-348ISBN: 91-7178-077-7 (print)OAI: oai:DiVA.org:kth-348DiVA: diva2:9283
Presentation
2005-06-16, E2, Lindstedtsvägn 3, Stockholm, 10:00
Supervisors
Note
QC 20101217Available from: 2005-08-01 Created: 2005-08-01 Last updated: 2010-12-17Bibliographically approved
List of papers
1. Phase Equilibria and Thermodynamics of p-Hydroxybenzoic acid
Open this publication in new window or tab >>Phase Equilibria and Thermodynamics of p-Hydroxybenzoic acid
2006 (English)In: Journal of Pharmaceutical Sciences, ISSN 0022-3549, E-ISSN 1520-6017, Vol. 95, no 4, 748-760 p.Article in journal (Refereed) Published
Abstract [en]

The prevalence of phases and associated solubilities of p-hydroxybenzoic acid have been investigated in methanol, acetonitrile, acetic acid, acetone, water, and ethyl acetate at temperatures from 10 to 50 degrees C. Thermodynamic data was acquired through determination of van't Hoff enthalpy of solution, enthalpy of fusion, and melting temperature. Indications of polymorphic enantiotropy were found primarily through solubility analysis and FTIR-ATR. A comprehensive thermodynamic investigation disclosed correlation between the van't Hoff enthalpy of solution and the solubility in different solvents. A higher solubility is linked to a lower van't Hoff enthalpy of solution. A thermodynamic analysis to discriminate between different solid phases is presented.

Keyword
p-hydroxybenzoic acid, 4-hydroxybenzoic acid, polymorphism, pseudopolymorphism, solvate, complexation, solubility, desolvation, solid state stability, van't Hoff
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-8414 (URN)10.1002/jps.20569 (DOI)000236485300004 ()2-s2.0-33645991201 (Scopus ID)
Note
QC 20100831Available from: 2008-05-12 Created: 2008-05-12 Last updated: 2010-12-17Bibliographically approved
2. Solubility and thermodynamics of salicylic acid
Open this publication in new window or tab >>Solubility and thermodynamics of salicylic acid
(English)Article in journal (Other academic) Submitted
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-27633 (URN)
Note
QS 20120328Available from: 2010-12-17 Created: 2010-12-17 Last updated: 2012-03-28Bibliographically approved
3. Polymorphism and Thermodynamics of m-Hydroxybenzoic acid
Open this publication in new window or tab >>Polymorphism and Thermodynamics of m-Hydroxybenzoic acid
2006 (English)In: European Journal of Pharmaceutical Sciences, ISSN 0928-0987, E-ISSN 1879-0720, Vol. 28, no 5, 377-384 p.Article in journal (Refereed) Published
Abstract [en]

Solution and solid-state properties of m-hydroxybenzoic acid have been investigated. Two polymorphs were found where the monoclinic modification exhibits a higher stability than the orthorhombic form. The solubility of the monoclinic polymorph was determined between 10 and 50 degrees C in methanol, acetonitrile, acetic acid, acetone, water and ethyl acetate. The solubility of the orthorhombic polymorph was determined between 10 and 50 degrees C in acetonitrile, acetic acid, acetone and ethyl acetate. A thermodynamic analysis revealed a marked correlation between the molar solubility and the van't Hoff enthalpy of solution at constant temperature. In addition, in each solvent increased temperature resulted in increased van't Hoff enthalpy of solution. It is shown that the solubility data can be used to estimate melting properties for both polymorphs. The solubility ratio of the two forms and the DSC thermogram of the orthorhombic form strongly suggest that the system is monotropic. However, according to the polymorph rules of Burger and Ramberger, the estimated higher melting enthalpy and lower melting temperature of the orthorhombic form points towards an enantiotropic system. Hence, this system appears to be an exception to the Burger and Ramberger melting enthalpy rule, and the probable reason for this is found in the difference in the heat capacity of the two solid forms.

Keyword
m-hydroxybenzoic acid, 3-hydroxybenzoic acid, polymorphism, monotropy, enantiotropy, solubility, van't Hoff enthalpy of solution, thermodynamics
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-8415 (URN)10.1016/j.ejps.2006.04.008 (DOI)000239682800003 ()2-s2.0-33745841320 (Scopus ID)
Note
QC 20100831Available from: 2008-05-12 Created: 2008-05-12 Last updated: 2010-12-17Bibliographically approved
4. Solubility and thermodynamics of salicylamide
Open this publication in new window or tab >>Solubility and thermodynamics of salicylamide
(English)Manuscript (preprint) (Other academic)
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-27634 (URN)
Note
QC 20101217Available from: 2010-12-17 Created: 2010-12-17 Last updated: 2010-12-17Bibliographically approved

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