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Thermodynamics of the Enantiotropic Pharmaceutical Compound Benzocaine and Solubility in Pure Organic Solvents
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- Cheuk, Dominic (author)
- Univ Limerick, Synth & Solid State Pharmaceut Ctr, Bernal Inst, Dept Chem & Environm Sci, Castletroy, Ireland.
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- Svärd, Michael, Docent, 1976- (author)
- KTH,Teknisk strömningslära
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- Rasmuson, Åke C. (author)
- KTH,Teknisk strömningslära,Univ Limerick, Synth & Solid State Pharmaceut Ctr, Bernal Inst, Dept Chem & Environm Sci, Castletroy, Ireland.
- Univ Limerick, Synth & Solid State Pharmaceut Ctr, Bernal Inst, Dept Chem & Environm Sci, Castletroy, Ireland Teknisk strömningslära (creator_code:org_t)
- Elsevier BV, 2020
- 2020
- English.
- In: Journal of Pharmaceutical Sciences. - : Elsevier BV. - 0022-3549 .- 1520-6017. ; 109:11, s. 3370-3377
- Journal article (peer-reviewed)
Abstract
Subject headings
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- 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 degrees C-30 degrees 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- Solubility
- Polymorphism
- Crystallization
- Thermodynamics
- Activity coefficient
- Ideality
- Heat capacity
Publication and Content Type
- ref (subject category)
- art (subject category)
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