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Molecules 2015, 20(8), 15175-15191; doi:10.3390/molecules200815175

Characterization of the Sublimation and Vapor Pressure of 2-(2-Nitrovinyl) Furan (G-0) Using Thermogravimetric Analysis: Effects of Complexation with Cyclodextrins

1
Departamento de Farmacia, Facultad de Química y Farmacia, Carretera a Camajuaní km 5½, Universidad Central de Las Villas, 54830 Villa Clara, Cuba
2
Department of Metallurgy and Material Engineering, Kasteelpark Arenberg 44, University of Leuven (KU Leuven), BE-3001 Heverlee, Belgium
3
Centro de Bioactivos Químicos, Carretera a Camajuaní km 5½, Universidad Central de Las Villas, 54830 Villa Clara, Cuba
4
Drug Delivery and Disposition, Department of Pharmaceutical and Pharmacological Sciences, O & N2 Herestraat 49-Box 921, University of Leuven (KU Leuven), BE-3000 Leuven, Belgium
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editors: Thomas Rades, Holger Grohganz and Korbinian Löbmann
Received: 3 July 2015 / Revised: 15 August 2015 / Accepted: 17 August 2015 / Published: 19 August 2015
(This article belongs to the Collection Poorly Soluble Drugs)
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Abstract

In the present work, the sublimation of crystalline solid 2-(2-nitrovinyl) furan (G-0) in the temperature range of 35 to 60 °C (below the melting point of the drug) was studied using thermogravimetric analysis (TGA). The sublimated product was characterized using Fourier-transformed-infrared spectroscopy (FT-IR) and thin layer chromatography (TLC). The sublimation rate at each temperature was obtained using the slope of the linear regression model and followed apparent zero-order kinetics. The sublimation enthalpy from 35 to 60 °C was obtained from the Eyring equation. The Gückel method was used to estimate the sublimation rate and vapor pressure at 25 °C. Physical mixtures, kneaded and freeze-dried complexes were prepared with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and sulfobutyl ether-β-cyclodextrin (SBE-β-CD) and analyzed using isothermal TGA at 50 °C. The complexation contributed to reducing the sublimation process. The best results were achieved using freeze-dried complexes with both cyclodextrins. View Full-Text
Keywords: 2-(2-nitrovinyl) furan; cyclodextrins; thermogravimetry; sublimation enthalpy; vapor pressure 2-(2-nitrovinyl) furan; cyclodextrins; thermogravimetry; sublimation enthalpy; vapor pressure
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ruz, V.; González, M.M.; Winant, D.; Rodríguez, Z.; Van den Mooter, G. Characterization of the Sublimation and Vapor Pressure of 2-(2-Nitrovinyl) Furan (G-0) Using Thermogravimetric Analysis: Effects of Complexation with Cyclodextrins. Molecules 2015, 20, 15175-15191.

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