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

Molecules. 2015 Aug 19;20(8):15175-91. doi: 10.3390/molecules200815175.

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.

Keywords: 2-(2-nitrovinyl) furan; cyclodextrins; sublimation enthalpy; thermogravimetry; vapor pressure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Calorimetry, Differential Scanning
  • Cyclodextrins / chemistry*
  • Freeze Drying
  • Furans / chemistry*
  • Regression Analysis
  • Spectroscopy, Fourier Transform Infrared
  • Temperature
  • Thermogravimetry
  • Time Factors
  • Vapor Pressure*
  • Vinyl Compounds / chemistry*
  • beta-Cyclodextrins / chemistry

Substances

  • Cyclodextrins
  • Furans
  • Vinyl Compounds
  • beta-Cyclodextrins
  • trans-2-(2-nitrovinyl)furan
  • 2-Hydroxypropyl-beta-cyclodextrin
  • SBE4-beta-cyclodextrin