Glyoxylic Acid → Glyphosate
Reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[NH2:6][CH2:7][P:8]([OH:11])(=[O:10])[OH:9]>O>[P:8]([CH2:7][NH:6][CH2:2][C:1]([OH:5])=[O:4])([OH:11])([OH:10])=[O:9]Participants
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
29.6 g (0.2 mol) of 50% strength aqueous glyoxylic acid solution were warmed to 40° C. with stirring. 11.1 g (0.1 mol) of aminomethanephosphonic acid were then added in portions at 40°-45° C., whereupon a vigorous evolution of gas commenced. After completion of the addition, the temperature was increased to an internal temperature of 85° C. After about 1 h, the evolution of gas was complete. The mixture was stirred for a further 15 min at 85° C., a little water was added, and the mixture was cooled. 10 g of N-phosphonomethylglycine, m.p.: 321°-323° C. [decomp.], were obtained. After concentration of the mother liquor and digestion of the precipitated crystal slurry using methanol/water, a further 2.5 g were obtained. The total yield was thus 74% of theory.
Workup
- additionAfter completion of the addition
- stirringThe mixture was stirred for a further 15 min at 85° C.
- temperaturethe mixture was cooled
Sources & evidence
- ORD record
- ord-3b0b2654289941da92f84835390ce89d
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04670191
Reaction notes
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