Solubility dependence of peracylated d-glucopyranoses in supercritical carbon dioxide on the structure of their acyl moieties

Alan H. Haines, David C. Steytler, Carl Rivett

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10 Citations (Scopus)


Identification of chemical groups that enhance solubility of hydrocarbon-based surfactants and polymers in CO2 is of current interest in expanding applications of this 'green solvent'. In particular, the acetyl moiety is believed to solvate effectively in CO2 through a Lewis acid-base interaction between the carbonyl oxygen and CO2 carbon and this is further enhanced by specific weak H-bonding interaction of the α-hydrogens with the CO2 oxygen. In this communication we investigate the influence of this weak secondary interaction further by measurement of CO2 solubility of a range of β-d-glucopyranose pentaalkanoates containing as the acyl functionality acetyl, propionyl, butyryl, isobutyryl and trimethylacetyl (pivaloyl) groups. The results show that progressive replacement of the α-hydrogens of the acetyl by methyl results initially in a remarkable drop in solubility but surprisingly this is regained in the trimethylacetyl derivative that demonstrates a similarly high solubility to that of the acetyl compound.

Original languageEnglish
Pages (from-to)21-24
Number of pages4
JournalJournal of Supercritical Fluids
Issue number1
Publication statusPublished - Feb 2008


  • Carbon dioxide
  • Molecular interactions
  • NIR spectroscopy
  • Solubility
  • Supercritical fluids

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