Glycine → Glyphosate

HRID 1995517Notes

Reaction equation

HRID 1995517 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].Cl[CH2:7][P:8](=[O:11])([OH:10])[OH:9].[OH-].[Na+]>O>[P:8]([CH2:7][NH:1][CH2:2][C:3]([OH:5])=[O:4])([OH:11])([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 750GlycineHCID 14798Sodium Hydroxide3×HCID 75723P-(Chloromethyl)phosphonic acid

Product 1

HCID 3496Glyphosate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of about 50 parts of glycine, 92 parts of chloromethylphosphonic acid, 150 parts of 50% aqueous sodium hydroxide and 100 parts water was introduced into a suitable reaction vessel and maintained at a reflux temperature while an additional 50 parts of 50% aqueous sodium hydroxide was added. The pH of the reaction mixture was maintained between 10 and 12 by the rate of addition of the sodium hydroxide. After all of the caustic solution had been added, the reaction mixture was refluxed for an additional 20 hours, cooled to room temperature and filtered. About 160 ml. of concentrated hydrochloric acid were then added and the mixture filtered to provide a clear solution which slowly deposited N-phosphonomethylglycine. This material had a melting point of 230° C. with decomposition.

Workup

  1. additionwas introduced into a suitable reaction vessel
  2. additionwas added
  3. additionAfter all of the caustic solution had been added
  4. temperaturethe reaction mixture was refluxed for an additional 20 hours
  5. filtrationfiltered
  6. additionof concentrated hydrochloric acid were then added
  7. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-df48e84d789c4ada856ee6032fd11649
Source dataset
uspto-grants-1983_09
Patent number
US04405531

Reaction notes

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