Formaldehyde → N-acetyliminodiacetic acid

HRID 1883253Notes

Reaction equation

HRID 1883253 reaction equation
[N:1]([C:12]([CH3:14])=[O:13])([CH2:7]NC(C)=O)[CH2:2]NC(C)=O.C1[CH2:19][O:18]CC1.C=[O:21].NC[C:24]([OH:26])=[O:25]>C(O)(=O)C>[C:12]([N:1]([CH2:2][C:19]([OH:18])=[O:21])[CH2:7][C:24]([OH:26])=[O:25])(=[O:13])[CH3:14]

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 750GlycineHCID 8028TetrahydrofuranHCID 23599706HCID 23599706, compound

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A 2 L autoclave was charged with acetamide (VII) (129.8 g, 2.2 mole), THF (1 L), and acetic acid (45 g) and was purged with argon for 10 min. Under the argon purge, Co2(CO)8 (20.9 g, 0.06 mole) was added. After sealing the autoclave, 150 psi (1034 kPa) of CO:H2 (95:5) was established at 25° C. and was slowly vented. Then 2200 psi (15,172 kPa) of CO:H2 (95:5) was established at 25° C. with stirring at 2000 rpm. The contents of the autoclave were heated to 100° C. and 3200 psi (22,069 kPa) CO:H2 (95:5) was established. Under a constant 3200 psi (22,069 kPa), 47 Wt. % formalin (320 mL, 5.28 mole) was delivered at 40 mL/min. The reaction was stirred at 100° C. for 52 min. after the formalin addition was complete. Then the reaction was cooled to 25° C., removed from the autoclave, and assayed for N-acetyliminodiacetic acid. This resulted in a 95% yield of (XVI) and 1% glycine.

Workup

  1. customwas purged with argon for 10 min
  2. customUnder the argon purge
  3. customwas established at 25° C.
  4. customwas established at 25° C.
  5. stirringThe reaction was stirred at 100° C. for 52 min.
  6. temperatureThen the reaction was cooled to 25° C.
  7. customremoved from the autoclave

Sources & evidence

ORD record
ord-1258aec694bc4dda85ac6cb9dc981920
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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