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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis and Characterization of Long-Chain 1,2-Dioxo Compounds

Author
item Knothe, Gerhard

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 28, 2002
Publication Date: N/A

Interpretive Summary: The properties of industrial products such as biodiesel or lubricants, which can be derived from vegetable oils or animal fats can often be improved by adding other materials in small amounts. Such materials (termed additives) are designed to have a specific effect on one or more properties of the industrial products. It is especially desirable to derive these additives from the same material as the industrial products whose properties they should improve. The only difference is that the additives would need to be subjected to different processes, usually chemical reactions, to make them. This work describes the synthesis of chemical compounds which have the potential to be additives or which could be processed further into other compounds which may be suitable as additives. Methods to analyze the compounds synthesized here are discussed.

Technical Abstract: A series of long-chain methyl esters with vicinal oxo groups (1,2-diones; 1,2-diketones) were synthesized by potassium permanganate-based oxidation. The presence of two additional carbonyl groups may facilitate the synthesis of other derivatives. The starting materials were selected in such a fashion to give the 1,2-dioxo moiety in consecutive positions from the methyl ester group. The compounds were characterized by mass spectrometry and nuclear magnetic resonance spectroscopy. In mass spectrometry, both electron and chemical ionization (methane as reagent gas) were investigated. The position of the dioxo moiety can be defined in both ionization modes, however, in electron ionization mode the corresponding peaks are considerably stronger. In electron ionization mode, a fragmentation mechanism depending on the position of the 1,2-dioxo moiety occurs while the spectra derived from chemical ionization mode are mainly characterized by peaks around the molecular ion with both ionization modes appearing suitable.

Last Modified: 11/28/2014
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