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

HRID 629846Notes

Reaction equation

HRID 629846 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[P:10]([OH:13])([OH:12])[OH:11].P(=O)(O)(O)O.[CH2:19]=O>>[P:10]([CH2:19][N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])([OH:13])([OH:12])=[O:11]

Participants

5

Reactant 4

HCID 712Formaldehyde2×HCID 1004Phosphoric AcidHCID 8897Iminodiacetic acidHCID 107909Phosphorous acid

Product 1

HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineYield 61.2%

Conditions

Temperature
140 °C

Procedure

In a three-necked round-bottom flask equipped with a mechanical stirrer, 33.28 g (0.25 mol) of iminodiacetic acid (IDA) were mixed with 20.5 g (0.25 mol, 1 eq.) of phosphorous acid and 122.5 g (1.25 mol, 5 eq.) of phosphoric acid. The reaction mixture was heated to 140° C. 20.68 ml of 36.6 wt.-% aqueous solution of formaldehyde (1.1 eq.) were then added over 60 min. During the addition, the temperature of the reaction mixture decreased from 140° C. to 125° C. At the end of the formaldehyde addition the reaction mixture was kept at reflux for 30 min. The precipitate formed by cooling the reaction mixture was isolated by filtration and washed with fresh water. After drying the precipitate was analysed by 1H and 31P NMR and identified as 81.3% pure N-(phosphonomethyl)iminodiacetic acid (PMIDA, 28 g, 61.2% yield).

Workup

  1. customIn a three-necked round-bottom flask equipped with a mechanical stirrer
  2. additionDuring the addition
  3. customdecreased from 140° C. to 125° C
  4. temperatureat reflux for 30 min
  5. customThe precipitate formed
  6. temperatureby cooling the reaction mixture
  7. customwas isolated by filtration
  8. washwashed with fresh water
  9. customAfter drying the precipitate

Sources & evidence

ORD record
ord-763f5bd594dc449687188a8ccbe11321
Source dataset
uspto-grants-2016_04
Patent number
US09315528B2

Reaction notes

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