Hydrogen Peroxide → Glyphosate

HRID 1605530Notes

Reaction equation

HRID 1605530 reaction equation
S(=O)(=O)(O)O.[P:6]([CH2:10][N:11](CC(O)=O)[CH2:12][C:13]([OH:15])=[O:14])([OH:9])([OH:8])=[O:7].OO>O>[P:6]([CH2:10][NH:11][CH2:12][C:13]([OH:15])=[O:14])([OH:9])([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 1118Sulfuric AcidHCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycine2×

Product 1

HCID 3496Glyphosate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Thirty-nine parts of water and 39 parts of concentrated sulfuric acid were charged into a suitable reaction vessel and then 20 parts of N-(phosphonomethyl) iminodiacetic acid added. The mixture was heated to 80°C. and then 277 parts of a 35% hydrogen peroxide solution was added over a period of from 61/2 to 7 hours while maintaining the temperature at 77°-81°C. During the addition of the hydrogen peroxide, 8 additional 20 part increments of N-(phosphonomethyl) iminodiacetic acid were added over a 4 hour period. The reaction was then heated at 80°C. with stirring until nuclear magnetic resonance spectral analysis showed that the reaction was essentially complete. The mixture was then cooled at 0°C. overnight, centrifuged, washed with a small amount of water and dried under vacuum to yield approximately 100 parts of N-phosphonomethyl glycine.

Workup

  1. temperaturewhile maintaining the temperature at 77°-81°C
  2. additionwere added over a 4 hour period
  3. temperatureThe reaction was then heated at 80°C.
  4. temperatureThe mixture was then cooled at 0°C. overnight
  5. washcentrifuged, washed with a small amount of water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c7402059f4c64bb79e2af33f335c5193
Source dataset
uspto-grants-1976_04
Patent number
US03950402

Reaction notes

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