Optimization of 2-chloroethylphosphonic acid synthesis by acid hydrolysis of dialkyl-2-chloroethylphosphonate compounds. Influence of the nature of alkyl phosphonate functions
2-Chloroethylphosphonic acid (ethephon) 1 is very much used in agriculture as a plant regulator.It is an especially good stimulant used to increase the latex production of Hevea brasiliensis.Ethephon is generally obtained by HCl hydrolysis of bis(2-chloroethyl)-2-chloroethylphosphonate, previously prepared by Arbuzov rearrangement of tri(2-chloroethyl)phosphite.However, because of the low reactivity of 2-chloroethylphosphonate functions towards acid hydrolysis, this synthetic way is not convenient to prepare pure 2-chloroethylphosphonic acid with high yields.The present purpose was to study the hydrolysis of various dialkyl-2-chloroethylphosphonates in view to define an efficient synthetic protocol, leading to very pure crystallized ethephon with high yields. - Keywords: 2-chloroethylphosphonic acid; ethephon; dialkyl-2-chloroethylphosphonate; Arbuzov reaction; trialkyl phosphite; acid hydrolysis
Cauret, Laurent,Brosse, Jean-Claude,Derouet, Daniel,Livonniere, Hugues De
p. 463 - 470
(2007/10/03)
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