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https://doi.org/10.37358/Rev.Chim.1949

OSIM Nr. R102355
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Revista de Chimie (Rev. Chim.), Year 2006, Volume 57, Issue 6,





Chloroalkylesters Hydrolysis of Some
Chloroalkylphosphonic Acids in Hydrofluoric Acid Water Solutions

Abstract:

The paper presents the results obtained by the hydrolysis of chloroalkylesters of some chloroalkylphosphonic acids in hydrofluoric acid water solution, at 95 oC and atmospheric pressure. In the presence of hydrofluoric acid, hydrolysis takes place selectively, at high speed and quantitative yield, in contrast with the hydrochloric and hydrobromic acids, that is dominated by acidolysis and takes place at low speed. A reaction mechanism based on the exceptional nucleophylicity of the fluoride and fluoronium ions for the phosphorus atom is proposed. Their reduced afinity for the carbon atom in water solution and the mild conditions avoids the halogen exchange and the hydrolysis within the chloroalkyl group attached to the phosphorus atom. We present the gaschromatographic retention parameters for the initial esters, the monoesters and the phosphonic acids derivatised as methylesters. The mass spectrum of the dimethylesters of the chloroalkylphosphonic acids contain the characteristic peaks (M+1)+ and (M-Cl)+. Key words: chloroalkylphosphonic acids, hydrofluoric acid, hydrolysis, nucleophilic substitution


Issue: 2006, Volume 57, Issue 6
Pages:
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