Oxygen → Glyphosate

HRID 1605531Notes

Reaction equation

HRID 1605531 reaction equation
[P:1]([CH2:5][N:6](CC(O)=O)[CH2:7][C:8]([OH:10])=[O:9])([OH:4])([OH:3])=[O:2].O=O>[Pd].O>[P:1]([CH2:5][NH:6][CH2:7][C:8]([OH:10])=[O:9])([OH:4])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 977Oxygen2×HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycine

Product 1

HCID 3496GlyphosateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 10 g. of N-(phosphonomethyl) iminodiacetic acid, 170 mls. of water and 0.6 g. of commercial 5% palladium on carbon catalyst was placed in a pressure vessel and oxygen admitted to a pressure of 30 pounds per square inch. The mixture was continuously shaken at this pressure for 3 hours while maintaining the temperature at 90°-100°C. After cooling to room temperature, excess oxygen was vented, the catalyst removed by filtration and the filtrate concentrated to dryness at reduced pressure. The yield of 97% pure N-phosphonomethyl glycine was 7.3 g. (96% yield).

Workup

  1. additionA mixture of 10 g
  2. temperaturewhile maintaining the temperature at 90°-100°C
  3. customthe catalyst removed by filtration
  4. concentrationthe filtrate concentrated to dryness at reduced pressure

Sources & evidence

ORD record
ord-9b664a09ad7740a899c853e62b0e5e45
Source dataset
uspto-grants-1976_04
Patent number
US03950402

Reaction notes

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