Glycine → Glyphosate

HRID 1589106Notes

Reaction equation

HRID 1589106 reaction equation
[CH:1]([P:3](=[O:6])([OH:5])[OH:4])=O.[NH2:7][CH2:8][C:9]([OH:11])=[O:10].[OH-].[Na+].[H][H]>O.[Pd]>[P:3]([CH2:1][NH:7][CH2:8][C:9]([OH:11])=[O:10])([OH:5])([OH:4])=[O:6]

Participants

7

Reactant 4

HCID 750GlycineHCID 14798Sodium HydroxideHCID 10154022Formylphosphonic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 3496GlyphosateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a 59% aqueous formylphosphonic acid solution (5.0 g; 0.23 mol) in deionized water (25 ml) was added glycine (1.56 g; 0.021 mol). The pH of the resultant mixture was adjusted to 7.0 by addition of 2.5N sodium hydroxide. The reaction mixture was then transferred to a 300 ml autoclave, a 10% palladium on carbon catalyst (1.0 g) added, and the reactor sealed and pressurized with hydrogen to 6.89×106N/m2 gauge. After 60 minutes of reaction at room temperature, 3.2 g of N-phosphonomethylglycine was obtained representing a 91% yield on glycine.

Workup

  1. customthe reactor sealed
  2. customAfter 60 minutes of reaction at room temperature

Sources & evidence

ORD record
ord-26b0cbb3066f462bbfef4320f4e4263e
Source dataset
uspto-grants-1986_02
Patent number
US04568432

Reaction notes

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