New bis(alkythio) fatty acid methyl esters

Authors: Knothe, Gerhard

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 4/30/2017
Publication Date: 4/30/2017
Citation: Knothe, G.H. 2017. New bis(alkythio) fatty acid methyl esters [abstract]. American Oil Chemists' Society Annual Meeting. p. 65.

Interpretive Summary:

Technical Abstract: The addition reaction of dimethyl disulfide (DMDS) to mono-unsaturated fatty acid methyl esters is well-known for analytical purposes to determine the position of double bonds by mass spectrometry. In this work, the classical iodine-catalyzed reaction is expanded to other dialkyl disulfides (RSSR), including diethyl disulfide (DEDS), dipropyl disulfide (DPDS), dibutyl disulfide (DBDS), di-iso-propyl disulfide (DiPDS), and di-tert-butyl disulfide (DtBDS). Yields decrease with increasing length or branching of the alkyl moieties in the RSSR. While mass spectrometry analysis is straightforward for the new derivatives, similar to the derivatization with DMDS, 1H- and 13C-NMR spectroscopy is now also extensively applied. The compounds exhibit various interesting effects in NMR, including the possibility to distinguish erythro- and threo-diastereomers. In addition, initial investigations indicate potentially interesting properties of these compounds for a variety of applications.