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Molecular inclusion of butylated hydroxyanisole (BHA) into alpha and beta cyclodextrins

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Abstract

BHA (butylated hydroxyanisole) was complexed with α- and β-cyclodextrins with the objective of characterizing the thermal stability. From phase solubility diagrams, the association constants for the complexes of α-CD:BHA and β-CD:BHA were found as 49.3 and 585 L mol−1, respectively. To increase the thermal stability of BHA, its molecular encapsulation in α-CD and β-CD, was tested using molar ratios of 1:1 and 1:2 (BHA:CD) and the complex preparation techniques of kneading and physical mixture. The products of complexation were characterized by differential scanning calorimetry and thermogravimetry, indicating the formation of a BHA:β-CD complex and showing that the release of the complexed BHA occurs in the temperature range of 280–350 °C, well above the temperature at which BHA sublimates. Dissolution tests have shown that the BHA: β-CD complex produced by kneading has high efficiency of dissolution and partition coefficient experiments demonstrated that the presence of β-CD leads to higher concentration of BHA in the organic phase.

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Acknowledgments

We are grateful to the supporting institutions: CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) and UEM (Universidade Estadual de Maringá).

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Correspondence to Carlos Eduardo Barão.

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Barão, C.E., Zanin, G.M. & de Moraes, F.F. Molecular inclusion of butylated hydroxyanisole (BHA) into alpha and beta cyclodextrins. J Incl Phenom Macrocycl Chem 71, 179–187 (2011). https://doi.org/10.1007/s10847-011-9925-6

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Keywords

  • Butylated hydroxyanisole
  • Cyclodextrins
  • Complex
  • Inclusion