Formaldehyde → N-(Carboxymethyl)-N-(phosphonomethyl)glycine

HRID 366915Notes

Reaction equation

HRID 366915 reaction equation
O.[C:2]([N:5]([CH2:10][C:11]([OH:13])=[O:12])[CH2:6][C:7]([OH:9])=[O:8])(=O)C.[P:14]([OH:17])([OH:16])[OH:15].O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C=O>O>[P:14]([CH2:2][N:5]([CH2:10][C:11]([OH:13])=[O:12])[CH2:6][C:7]([OH:9])=[O:8])([OH:17])([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 107909Phosphorous acidHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 86755940HCID 86755940, compound

Product 1

HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A pressure reactor was charged with N-acetyliminodiacetic acid monohydrate (19.3 g), water (16.6 g), phosphorous acid (9.8 g) and toluenesulfonic acid monohydrate (35.2 g). The mixture was heated to 120° C. and 47% formaldehyde (5.8 mL) was added drop wise over a 3/4 hour period. After another 3/4 hour at 120° C. the mixture was cooled. The mixture was filtered and the solid was washed with water to give 16.5 g of N-(phosphonomethyl)iminodiacetic acid.

Workup

  1. temperatureAfter another 3/4 hour at 120° C. the mixture was cooled
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with water

Sources & evidence

ORD record
ord-6dc546e05c104a8cab69929a63f4fb68
Source dataset
uspto-grants-2000_10
Patent number
US06130351

Reaction notes

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