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Issue 21, 2015

Investigation into solid and solution properties of quinizarin

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Abstract

Polymorphism, crystal shape and solubility of 1,4-dihydroxyanthraquinone (quinizarin) have been investigated in acetic acid, acetone, acetonitrile, n-butanol and toluene. The solubility of FI and FII from 20 °C to 45 °C has been determined by a gravimetric method. By slow evaporation, pure FI was obtained from n-butanol and toluene, pure FII was obtained from acetone, while either a mixture of the two forms or pure FI was obtained from acetic acid and acetonitrile. Slurry conversion experiments have established an enantiotropic relationship between the two polymorphs and that the commercially available FI is actually a metastable polymorph of quinizarin under ambient conditions. However, in the absence of FII, FI is kinetically stable for many days over the temperature range and in the solvents investigated. FI and FII have been characterized by infrared spectroscopy (IR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), scanning electron microscopy (SEM), transmission and ordinary powder X-ray diffraction (PXRD) at different temperatures. The crystal structure of FII has been determined by single-crystal XRD. DSC and high-temperature PXRD have shown that both FI and FII will transform into a not previously reported high-temperature form (FIII) around 185 °C before this form melts at 200–202 °C. By indexing FIII PXRD data, a triclinic P[1 with combining macron] cell was assigned to FIII. The solubility of quinizarin FI and FII in the pure organic solvents used in the present work is below 2.5% by weight and decreases in the order: toluene, acetone, acetic acid, acetonitrile and n-butanol. The crystal shapes obtained in different solvents range from thin rods to flat plates or very flat leaves, with no clear principal difference observed between FI and FII.

Graphical abstract: Investigation into solid and solution properties of quinizarin

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Article information


Submitted
22 Jan 2015
Accepted
21 Apr 2015
First published
21 Apr 2015

This article is Open Access

CrystEngComm, 2015,17, 3985-3997
Article type
Paper
Author version available

Investigation into solid and solution properties of quinizarin

D. Cheuk, M. Svärd, C. Seaton, P. McArdle and Å. C. Rasmuson, CrystEngComm, 2015, 17, 3985 DOI: 10.1039/C5CE00147A

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