Issue 22, 2014

Structure–function study of tertiary amines as switchable polarity solvents

Abstract

A series of tertiary amines have been screened for their function as switchable polarity solvents (SPS). The relative ratios of tertiary amine and carbonate species as well as maximum possible concentration were determined through quantitative 1H and 13C NMR spectroscopy. The viscosities of the polar SPS solutions were measured and ranged from near water in dilute systems through to gel formation at high concentrations. The van't Hoff indices for SPS solutions were measured through freezing point depression studies as a proxy for osmotic pressures. A new form of SPS with an amine : carbonate ratio significantly greater than unity has been identified. Tertiary amines that function as SPS at ambient pressures appear to be limited to molecules with fewer than 12 carbons. The N,N-dimethyl-n-alkylamine structure has been identified as important to the function of an SPS.

Graphical abstract: Structure–function study of tertiary amines as switchable polarity solvents

Article information

Article type
Paper
Submitted
17 Dec 2013
Accepted
31 Jan 2014
First published
03 Feb 2014

RSC Adv., 2014,4, 11039-11049

Author version available

Structure–function study of tertiary amines as switchable polarity solvents

A. D. Wilson and F. F. Stewart, RSC Adv., 2014, 4, 11039 DOI: 10.1039/C3RA47724J

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