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
| Autor: | Jordi Escabrós, Angel Messeguer, Ramon Crehuet |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Imidic acid
Reaction mechanism Intramolecular reaction Chemistry Computational studies Organic Chemistry medicine.disease Biochemistry Deodorisation Propanediol chemistry.chemical_compound Aniline Drug Discovery medicine Organic chemistry Anilides 3-N-Phenylamino-1 2-propanediol esters Amine gas treating Toxic Oil Syndrome Toxic oil syndrome Derivative (chemistry) |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2008.09.102 |
| Popis: | 9 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. A 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. This workwas supported by FISAT-WHO Grants. R.C. would like to thank the Ramón y Cajal program of the Spanish government and MEC for financial support (Grant CTQ2006-01345/BQU). This research has been partly performed using the CESCA resources. |
| Databáze: | OpenAIRE |
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