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Preparation of N-phosphonomethylglycine
| Details |
Inventors: Parry, David Rees; Tomlin, Clive Dudley Spencer;
Assignee: Imperial Chemical Industries Limited (London, EN)
Primary Examiner: Evans; Joseph E.
Assistant Examiner:
Attorney, Agent or Firm: Cushman, Darby & Cushman
A process of preparing the herbicide N-phosphonomethylglycine which comprises reacting an N-substituted glycine derivative of the formula: ##EQU1## wherein R.sup.1 is a hydrogen atom or an esterifying group, Ar is an aryl radical, and R.sup.2 and R.sup.3 each stand for a hydrogen atom or an aryl radical, with formaldehyde and phosphorous acid in an acidic aqueous medium to give an N-substituted N-phosphonomethylglycine derivative of the formula: ##EQU2## and thereafter reacting the said N-substituted N-phosphonomethylglycine with hydrobromic or hydriodic acid to remove the N-substituent, and recovering N-phosphonomethylglycine. |
|
DETAILED DESCRIPTION We claim: 1.
A process of preparing N-phosphonomethyl-glycine having the formula: ##EQU17## which comprises reacting an N-substituted glycine derivative of the formula: ##EQU18## wherein R.
sup.
1 is a hydrogen atom or an esterifying group, Ar is an aryl radical, and R.
sup.
2 and R.
sup.
3 are each selected from the group consisting of hydrogen atoms and aryl radicals, with formaldehyde and phosphorous acid in a nonoxidizing acidic aqueous medium to give an N-substituted-N-phosphonomethylglycine derivative of the formula: ##EQU19## and thereafter reacting the said N-substituted-N-phosphonomethylglycine with an acid selected from the group consisting of hydrobromic and hydriodic acids, and recovering N-phosphono-methylglycine.
2.
A process according to claim 1 wherein the nonoxidizing acidic aqueous medium comprises hydrochloric, hydrobromic, or hydriodic acid.
3.
A process according to claim 1, wherein the condensation of the N-substituted glycine derivative with formaldehyde and phosphorous acid is carried out at a temperature in the range from 100.
degree.
C to 150.
degree.
C.
Description:
EXAMPLE 1 This Example illustrates the preparation of N-benzyl-N-phosphonomethylglycine, having the formula: ##EQU16## N-Benzyl ethyl glycinate (120 g.
0.
622 M) prepared as set forth in the foregoing description, was dissolved in a mixture of dionised water (400 ml.
) and concentrated hydrochloric acid (140 ml.
) A solution of phosphorous acid (51.
0 g.
0.
622 M) in deionised water (100 ml.
) was added, and the solution heated to reflux.
Formalin solution (40% w/w formaldehyde solution in water 131 ml) was aded over 30 minutes, giving a light pink solution.
After heating for 1 hour under reflux, paraformaldehyde (30.
8 g) was added in portions over 10 minutes and the solution heated under reflux for a further 4 hours, slowly turning yellow in colour.
The solution was evaporated to dryness under reduced pressure and finally dried at 0.
1 millimeters pressure over phosphorus pentoxide
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