Formaldehyde → N-acetyliminodiacetic acid

HRID 1386863Notes

Reaction equation

HRID 1386863 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-6aa9fd0050304538b6537b2db3f1fb4c
Source dataset
uspto-grants-2001_07
Patent number
US06265605B1

Reaction notes

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