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Solid Forms, Crystal Habits, and Solubility of Danthron
Univ Limerick, Dept Chem & Environm Sci, Mat & Surface Sci Inst, Synth & Solid State Pharmaceut Ctr,.ORCID iD: 0000-0003-1790-2310
2015 (English)In: Journal of Chemical and Engineering Data, Vol. 60, no 7, p. 2110-2118Article in journal (Refereed) Published
Abstract [en]

The polymorphism, crystal habits, and solubility of 1,8-dihydroxyanthraquinone (danthron) were investigated in acetic acid, acetone, acetonitrile, n-butanol, and toluene. The solubility was determined for the commercially available form (FI) from 293.15 K to 318.15 K. by the gravimetric method. The influence of solvents on crystal habit and polymorphic form has been investigated. Three different crystal habits of danthron were obtained from slow evaporation and cooling experiments. By evaporation, thin squares of FI were obtained from n-butanol and toluene solutions while both FT and fine needles of FIT were obtained from acetone and acetonitrile solutions. In addition, needle-shaped solvate crystals were obtained from acetic acid solutions and the structure of the solvate was solved by single crystal X-ray diffraction. From cooling crystallization experiments, mixtures of FI and FIT were often obtained from various solvents, but FT and FIT possess distinct habits which can be easily distinguished by visual comparison. Slurry conversion experiments have established that FT is the thermodynamically stable polymorph of danthron at ambient conditions. Differntial scanning calorimetry (DSC) and high-temperature powder X-ray diffraction (PXRD) have shown that both FI and FII will transform into a high-temperature form (FIV) around 435 K to 439 K before this form melts at 468.5 K. FI, FIT, and FIV have been characterized by transmission and high-temperature PXRD, scanning electron microscopy, infrared spectrometry, Raman spectrometry, thermogravimetric analysis, and DSC. The solubility of danthron FI in the pure organic solvents of the present work and in the temperature range investigated is below 4.3 % by weight and decreases in the order toluene, acetone, acetonitrile, and n-butanol.

Place, publisher, year, edition, pages
2015. Vol. 60, no 7, p. 2110-2118
Keywords [en]
ANTHRAQUINONES; 1, 8-DIHYDROXYANTHRAQUINONE; MUTAGENICITY; QUINIZARIN; SPECTRA
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-260111DOI: 10.1021/acs.jced.5b00192ISI: 000357964000020Scopus ID: 2-s2.0-84937501252OAI: oai:DiVA.org:kth-260111DiVA, id: diva2:1355961
Note

Cited By :7; Export Date: 25 September 2019; Article

QC 20191011

Available from: 2019-09-30 Created: 2019-09-30 Last updated: 2019-10-11Bibliographically approved

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Rasmuson, Åke Christoffer
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