Method for preparation of n-phosphonomethylglycine

C - Chemistry – Metallurgy – 07 – F

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260/501.5

C07F 9/38 (2006.01) C07D 233/78 (2006.01) C07F 9/6506 (2006.01)

Patent

CA 1205817

METHOD FOR PREPARATION OF N-PHOSPHONOMETHYLGLYCINE Abstract of the Invention Disclosed is a method for the preparation of N-phosphonomethyl- glycine which comprises the steps of (a) reacting hydantoin or a 3-sub- stituted hydantoin, a compound of the formula Image wherein R is selected from the group consisting of hydrogen, alkyl having from 1 to 10 carbon atoms, aryl having from 6 to 12 carbon atoms, alkyl- carbonyl wherein the alkyl group has from 1 to 10 carbon atoms, and aryl- carbonyl wherein the aryl group has from 6 to 12 carbon atoms, with para- formaldehyde in the presence of a low molecular weight carboxylic acid at a temperature and for a sufficient period of time to produce a mixture of intermediate products, including the 1-hydroxymethyl derivative of the starting hydantion (b) converting said 1-hydroxymethyl derivative to the 1-phosphonomethyl derivative by thereafter adding to the reaction mixture either (i) a substituted phosphorus compound selected from the group con- sisting of phosphorus trichloride, and phosphorus tribromide; or (ii) adding to the reaction mixture phosphorous acid and a anhydride selected from the group consisting acetic anhydride, propionic anhydride, butyric anhydride, or mixture thereof, and continuing said reaction at a tenpera- ture and for a sufficient period of time to cause completion of the reac- tion to form the 1-phosphonomethyl derivative; and (c) hydrolyzing the 1-phosphonomethylhydantoin product thus formed with a base selected from the group consisting of alkali metal or alkaline earth hydroxide, to pro- duce a salt of N-phosphonomethylglycine; and (d) neutralizing said salt with a strong acid to produce the end product, N-phosphonomethylglycine.

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