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Studies on the Toxic Oil Syndrome: proposal of a mechanism for the thermal conversion of 3-N-phenylamino-1,2-propanediol esters into anilides under deodorisation conditions

AuthorsEscabrós, Jordi; Crehuet, Ramón ; Messeguer Peypoch, Ángel
KeywordsToxic Oil Syndrome
3-N-Phenylamino-1,2-propanediol esters
Computational studies
Reaction mechanism
Issue Date3-Jan-2009
CitationTetrahedron 65(1): 418-426 (2009)
AbstractA study on the reaction mechanism for the conversion of title esters, the species recognised as toxic biomarkers of the oil batches responsible for the Toxic Oil Syndrome, into the corresponding anilides under the thermal conditions of an oil deodorisation process was performed using experimental and computational techniques. The results obtained suggest a reaction course that includes two basic steps: an intramolecular process involving the reaction of the amine group of the diester derivative with the secondary ester of the same compound, followed by the attack of an aniline molecule to form the (E)-isomer of an imidic acid, which would finally tautomerise to give the final anilide.
Description9 pages, 4 figures.-- Supplementary information (Schemes S1-S2, figure S1, tables S1-S2 and suppl. data, 4 pages) available at the paper site.
Available online 10 October 2008.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2008.09.102
Appears in Collections:(IQAC) Artículos
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