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Characterizing the thermal phase behaviour of fipronil polymorphs

升华(心理学) 再结晶(地质) 亚稳态 结晶学 化学 多态性(计算机科学) 粉末衍射 溶剂 熔点 材料科学 有机化学 基因型 基因 古生物学 生物 生物化学 心理学 心理治疗师
作者
Dennis Simbarashe Moyo,Elizabet M. van der Merwe,M. Rademeyer,Frederick P. Malan,Maria Atanasova,António Benjamim Mapossa,Walter W. Focke
出处
期刊:Journal of Thermal Analysis and Calorimetry [Springer Science+Business Media]
卷期号:148 (14): 6761-6777 被引量:1
标识
DOI:10.1007/s10973-023-12198-x
摘要

Abstract This manuscript reports the investigation of the polymorphic behaviour of fipronil using a systematic comparison of the thermochemical and structural properties of different crystal forms obtained in this study as well as those previously reported in literature. The analytical techniques employed include DSC, TGA, PXRD, SCXRD and hot stage microscopy. DSC proved particularly useful because it made it possible to differentiate between the two different crystal forms found in the as-received neat fipronil. The DSC scans revealed the presence of two polymorphs which had melting endotherms with peak maxima at ca . 196 °C and 205 °C, respectively. These polymorphs were successfully separated via sublimation and resulted in a metastable, lower melting polymorph in the sublimate and a thermodynamically stable, higher melting form in the sublimation residue. Clear evidence for the instability of the lower melting polymorph was found when the endotherms were examined under a range of heating rates. The proportion of the metastable form appeared to increase as the rate was increased, indicating that the metastable form underwent a solid–solid phase transition to the stable form at low heating rates. Recrystallization of fipronil from different solvents yielded five different forms. TGA curves revealed that all forms, except the acetone-derived one, were solvate pseudo-polymorphs that showed solvent loss between 60 and 100 °C. The acetone-derived sample was a hemihydrate that only started to show mass loss at 120 °C. SCXRD studies revealed that three of the five forms have similar structural characteristics, while the other two forms differ notably from each other and the rest of the structures. Despite these structural differences, all five forms exhibit near-identical intra- and intermolecular hydrogen bond networks.
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