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

HRID 260571

Reaction equation

HRID 260571 reaction equation
[P:1]([OH:4])([OH:3])[OH:2].[NH:5]([CH2:10][C:11]([OH:13])=[O:12])[CH2:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH2:19]=O>>[P:1]([CH2:19][N:5]([CH2:10][C:11]([OH:13])=[O:12])[CH2:6][C:7]([OH:9])=[O:8])([OH:4])([OH:3])=[O:2]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric Acid3×HCID 8897Iminodiacetic acidHCID 107909Phosphorous acid

Product 1

HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineYield 95.9%

Conditions

Temperature
120 °C

Procedure

Concentrated filtrates from Cycle 1 were charged to a 500 ml three neck flask fitted with thermometer, condenser, dropping funnel and stirrer. Phosphorous acid (40.8 g, 0.493 moles), iminodiacetic acid (63.6 g, 0.469 moles) and sulphuric acid (5.0 g, 0.050 moles) were added, with stirrring, to the flask (sulphuric acid was charged on the assumption that 10% of the sulphuric acid was lost in the wash and filter cake). The reaction mixture was then heated to 120° C. and formaldehyde (46.1 g at 36.1% strength, 0.555 moles) was then added over one hour. The temperature was maintained between 110° and 120° C. during addition. On complete addition the reaction mixture was allowed to cool to 25° C. over 90 minutes. The reaction mixture was filtered and the filter cake washed with water (57 ml). The product was dried in a vacuum oven to yield 102.2 g of N-phosphonomethyliminodiacetic acid at 95.4% strength equivalent to a cumulative isolated yield of 75.3%. The filtrates (99.3 g) and the water wash (76.8 g) were analysed at 7.5% and 3.7% N-phosphonomethyliminodiacetic acid respectively. This was equivalent to a total cumulative conversion yield of 81.7% N-phosphonomethyliminodiacetic acid.

Workup

  1. customfitted with thermometer, condenser
  2. washwash
  3. filtrationfilter cake)
  4. temperatureThe temperature was maintained between 110° and 120° C. during addition
  5. additionOn complete addition the reaction mixture
  6. temperatureto cool to 25° C. over 90 minutes
  7. filtrationThe reaction mixture was filtered
  8. washthe filter cake washed with water (57 ml)
  9. customThe product was dried in a vacuum oven

Sources & evidence

ORD record
ord-10b21984e73a43a1a748890a86a19b27
Source dataset
uspto-grants-1996_06
Patent number
US05527953

Linked notes

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