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

Haines, Alan H., Steytler, David C. and Rivett, Carl (2008) Solubility dependence of peracylated d-glucopyranoses in supercritical carbon dioxide on the structure of their acyl moieties. Journal of Supercritical Fluids, 44 (1). pp. 21-24. ISSN 0896-8446

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Abstract

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.

Item Type: Article
Additional Information: Funding Information: Financial support for a CASE studentship for Carl Rivett from EPSRC and Infineum UK is gratefully acknowledged.
Uncontrolled Keywords: carbon dioxide,molecular interactions,nir spectroscopy,solubility,supercritical fluids,chemical engineering(all),condensed matter physics,physical and theoretical chemistry ,/dk/atira/pure/subjectarea/asjc/1500
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 14 Jul 2022 12:30
Last Modified: 12 Aug 2022 05:34
URI: https://ueaeprints.uea.ac.uk/id/eprint/86107
DOI: 10.1016/j.supflu.2007.08.007

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