Hydrogen Peroxide → Glyphosate

HRID 1076052Notes

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

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, additional N-(phosphonomethyl) iminodiacetic acid was added in 20 part increments over a 4 hour period. When visual observation showed the reaction mass was clear, that is, it contained no suspended solids, a sample was taken for nuclear magnetic resonance spectra analysis. The reaction was then continued to be heated at 80°C. with stirring until nuclear magnetic resonance spectra 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

temperaturewhile maintaining the temperature at 77°-81°C
additionwas added in 20 part increments over a 4 hour period
temperatureto be heated at 80°C.
temperatureThe mixture was then cooled at 0°C. overnight
washcentrifuged, washed with a small amount of water
customdried under vacuum

Sources & evidence

ORD record: ord-b87f4b9fc419404abbd15aecefcb1b83
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03954848

Reaction notes

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