Sodium Hydroxide → Glyphosate

HRID 1089365Notes

Reaction equation

HRID 1089365 reaction equation
[Na][Na].[OH2:3].[OH:4][CH2:5][CH2:6][N:7]([CH2:11][P:12](=[O:15])([OH:14])[OH:13])[CH2:8][CH2:9][OH:10].[OH-:16].[Na+]>O>[P:12]([CH2:11][N:7]([CH2:6][C:5]([OH:16])=[O:4])[CH2:8][C:9]([OH:3])=[O:10])([OH:14])([OH:13])=[O:15].[P:12]([CH2:11][NH:7][CH2:8][C:9]([OH:3])=[O:10])([OH:13])([OH:14])=[O:15].[NH2:7][CH2:11][P:12](=[O:13])([OH:15])[OH:14]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 141233DisodiumHCID 86744316HCID 86744316, compound

Product 3

HCID 3496GlyphosateYield 51.2%HCID 14017(Aminomethyl)phosphonic acidYield 10.2%HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineYield 33.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The disodium salt of [bis(2hydroxyethyl)amino]methylphosphonic acid monohydrate (10.0 g, 0.04 mol) was reacted in a 40% solution of sodium hydroxide (6.4 g, 0.16 mol) and water (10.0 g) at 270° C. for 130 minutes. The product mixture gave N-phosphonomethyliminodiacetic acid (2.76 g, 33.2%), N-phosphonomethylglycine (2.68 g, 51.2%) and aminomethylphosphonic acid (0.56 g, 10.2%).

Sources & evidence

ORD record
ord-066698cec50f465594b69eaf72cb3144
Source dataset
uspto-grants-1990_10
Patent number
US04965403

Reaction notes

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