Mechanisms of Degradation of Paraoxon in Different Ionic Liquids

Herein, the reactivity and selectivity of the reaction of O,O-diethyl 4-nitrophenyl phosphate triester (Paraxon, 1) with piperidine in ionic liquids (ILs), three conventional organic solvents (COS), and water is studied by 31P NMR, UV–vis, and GC/MS. Three phosphorylated products are identified as f...

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Published inJournal of organic chemistry Vol. 78; no. 19; pp. 9670 - 9676
Main Authors Pavez, Paulina, Millán, Daniela, Morales, Javiera I, Castro, Enrique A, López A, Claudio, Santos, José G
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.10.2013
Subjects
Ionic Liquids - chemistry
Magnetic Resonance Spectroscopy
Nitrobenzenes - chemistry
Paraoxon - chemistry
Piperidines - chemistry
Solvents - chemistry
Water
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Summary:Herein, the reactivity and selectivity of the reaction of O,O-diethyl 4-nitrophenyl phosphate triester (Paraxon, 1) with piperidine in ionic liquids (ILs), three conventional organic solvents (COS), and water is studied by 31P NMR, UV–vis, and GC/MS. Three phosphorylated products are identified as follows: O,O-diethyl piperidinophosphate diester (2), O,O-diethyl phosphate (3), and O-ethyl 4-nitrophenyl phosphate diester (4). Compound 4 also reacts with piperidine to yield O-ethyl piperidinophosphate monoester (5). The results show that both the rate and products distribution of this reaction depend on peculiar features of ILs as reaction media and the polarity of COS.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo401351v