Glycine → Glyphosate

HRID 650718Notes

Reaction equation

HRID 650718 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 2.5 N 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 was sealed and pressurized with hydrogen to 6.89×106 N/m2 gauge. After 60 minutes of reaction at room temperature, 3.2 g of N-(phosphonomethyl)glycine was obtained representing a 91% yield based on glycine.

Workup

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

Sources & evidence

ORD record
ord-3336889f14b54607a222d5ba40490a7e
Source dataset
uspto-grants-2001_08
Patent number
US06274760B1

Reaction notes

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