Recovery of host crystals from inclusion crystals of p-tert-butylcalix[4]arene and p-tert-butylthiacalix[4]arene by the treatment with a solvent and/or supercritical CO2

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Abstract

Upon stirring inclusion crystals of p-tert-butylthiacalix[4]arene (2) in solvents with heating, guest compounds were efficiently desorbed to yield guest-free crystals. More specifically, upon treatment with methanol, the exchange of guest compounds with methanol in the crystals, followed by the desorption of the methanol afforded metastable host crystals 2β, whereas, upon treatment with heptane, the dissolution of the inclusion crystals and simultaneous crystallization of compound 2 afforded stable host crystals 2α. Further, a host crystal of p-tert-butylcalix[4]arene (1) was recovered by the treatment of 2:1 (host/guest) inclusion crystals of compound 1 with supercritical carbon dioxide (scCO2), and through the combination of the guest exchange of 1:1 inclusion crystals of compound 1 with hexane and scCO2 treatment of the resulting 2:1 inclusion crystals 12·hexane. Although the recovered host crystal of compound 1 contained a small amount of CO2, it could be reused for the inclusion of organic compounds.

Original languageEnglish
Pages (from-to)279-285
Number of pages7
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume90
Issue number3-4
DOIs
Publication statusPublished - 2018 Apr 1

Keywords

  • Guest desorption
  • Inclusion crystal
  • p-tert-Butylcalix[4]arene
  • p-tert-Butylthiacalix[4]arene

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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