Issue 7, 2010

Fate of monoterpenes in near-critical water and supercritical alcohols assisted by microwave irradiation

Abstract

The rearrangement of α- and β-pinene was studied under microwave irradiation in near-critical water and supercritical lower aliphatic alcohols, with the aim of identifying the pathway of α- and β-pinene isomerization. Generally, two pathways occur, pyrolysis on the one and acidolysis on the other hand, whereby acidolysis is predominant in the case of near-critical water and the second pathway is favored for experiments employing supercritical alcohols. The different behavior of these two structurally related solvents is attributed to the increased availability of protons if water is heated to 270 °C and 80 bar, thus enhancing the autoprotolysis of water. The application of alcohols instead furnished rearrangement products clearly attributed to thermal pyrolysis route by the formation of radical reaction intermediates.

Graphical abstract: Fate of monoterpenes in near-critical water and supercritical alcohols assisted by microwave irradiation

Supplementary files

Article information

Article type
Paper
Submitted
05 Nov 2009
Accepted
09 Jan 2010
First published
01 Feb 2010

Org. Biomol. Chem., 2010,8, 1560-1567

Fate of monoterpenes in near-critical water and supercritical alcohols assisted by microwave irradiation

T. Szuppa, A. Stolle and B. Ondruschka, Org. Biomol. Chem., 2010, 8, 1560 DOI: 10.1039/B924748C

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