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

HRID 260574Notes

Reaction equation

HRID 260574 reaction equation
[P:1]([OH:4])([OH:3])[OH:2].S(=O)(=O)(O)O.[NH:10]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][C:12]([OH:14])=[O:13].[CH2:19]=O>O>[P:1]([CH2:19][N:10]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][C:12]([OH:14])=[O:13])([OH:4])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 8897Iminodiacetic acidHCID 107909Phosphorous acid

Product 1

HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
115 °C

Procedure

Water (11.2 g, 0.623 moles) was charged to a 500 ml three neck flask fitted with thermometer, condenser, dropping funnel and stirrer. The stirrer was started and phosphorous acid (42.6 g, at 99%; 0.514 moles) was added whereupon the temperature dropped from 20° C. to 12° C. Sulphuric acid (49.8 g at 98%, 0.498 moles) was then added over 10 minutes whilst maintaining the temperature below 50° C. with a water bath. Iminodiacetic acid (66.5 g at 95.4% strength, 0.479 moles) was then added to the reaction flask. The reaction mixture was heated to 115° C. and formaldehyde (48.2 g at 37.0% strength, 0.594 moles) was added over two hours. The temperature was maintained between 110° and 120° C. during addition. On complete addition, the reaction mixture was held at 115° C. for a furthre hour and then allowed to cool to 90° C. A second water charge (92.0 g) was added over 1 hour maintaining the temperature at approximately 90° C. during the addition. The reaction mixture was allowed to self-cool overnight. The slurry was filtered, washed with cold water (57.0 g) and the resulting product was dried at 60° C. in a vacuum oven overnight to give 100.2 g of N-phosphonomethyliminodiacetic acid at 95.7% strength, equivalent to an isolated yield of 88.1%. The filtrates (172.8 g) and the water wash (71.7 g) contained 4.8% and 1.2% N-phosphonomethyliminodiacetic acid respectively. This gave a total conversion yield of 93.5% N-phosphonomethyliminodiacetic acid.

Workup

  1. customfitted with thermometer, condenser
  2. additiondropped from 20° C. to 12° C
  3. temperaturewhilst maintaining the temperature below 50° C. with a water bath
  4. temperatureThe temperature was maintained between 110° and 120° C. during addition
  5. additionOn complete addition
  6. waitthe reaction mixture was held at 115° C. for a furthre hour
  7. temperatureto cool to 90° C
  8. additionwas added over 1 hour
  9. temperaturemaintaining the temperature at approximately 90° C.
  10. additionduring the addition
  11. temperatureto self-cool overnight
  12. filtrationThe slurry was filtered
  13. washwashed with cold water (57.0 g)
  14. customthe resulting product was dried at 60° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-ebc277bbff49470ea51ab0d5f0185991
Source dataset
uspto-grants-1996_06
Patent number
US05527953

Reaction notes

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