Glycine → Glyphosate

HRID 1589107Notes

Reaction equation

HRID 1589107 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH:6]([P:8](=[O:11])([OH:10])[OH:9])=O.[H][H]>>[CH2:2]([NH:1][CH2:6][P:8]([OH:11])([OH:10])=[O:9])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 750Glycine2×HCID 10154022Formylphosphonic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 3496GlyphosateYield 93.9%

Procedure

Reaction of glycine and formylphosphonic acid was carried out in the manner described in Example 2 except that the amount of glycine used was increased slightly (1.9 g; 0.025 mole), a smaller amount of catalyst was supplied (0.1 g), and the pH was adjusted to 8.0. The system was maintained at the reaction temperature and pressure for 20 hours although hydrogen uptake ceased after 0.5 hour. The analysis indicated a 93.9% yield of glyphosate salt.

Workup

  1. temperatureused was increased slightly (1.9 g; 0.025 mole)

Sources & evidence

ORD record
ord-de03e4543eb54df3be2bf0e12c332796
Source dataset
uspto-grants-1986_02
Patent number
US04568432

Reaction notes

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