Acetic Acid → N-acetyliminodiacetic acid

HRID 1859253Notes

Reaction equation

HRID 1859253 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[CH2:5]1[CH2:9][O:8]CC1.C=[O:11].[C:12]([OH:15])(=[O:14])[CH3:13]>>[C:1]([N:4]([CH2:5][C:9]([OH:8])=[O:11])[CH2:13][C:12]([OH:15])=[O:14])(=[O:3])[CH3:2].[C:1]([NH:4][CH2:13][C:12]([OH:15])=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 178AcetamideHCID 712Formaldehyde2×HCID 8028Tetrahydrofuran

Product 2

HCID 10972AcetylglycineYield 3%HCID 10130190N-acetyliminodiacetic acidYield 85%

Conditions

Temperature
130 °C

Procedure

A 2 L autoclave was charged with acetamide (VII) (128.5 g, 2.2 mole), Co(OAc)2 4H2O (33 g, 0.13 mole), THF (960 mL), and acetic acid (40 mL). After sealing the autoclave, 2200 psi (15,172 kPa) of CO:H2 (70:30) was established at 25° C. with stirring at 2000 rpm. The contents of the autoclave were heated to 130° C. and 3200 psi (22,069 kPa) CO:H2 (70:30) was established. After approximately 75 min., rapid gas uptake was observed. The contents of the autoclave were cooled to 85° C. and 3200 psi (22,069 kPa) was established with a CO:H2 (90:10) feed. Under a constant 3200 psi (22,069 kPa) (90:10/CO:H2 feed), 47 Wt. % formalin (320 mL, 5.28 mole) was delivered at 9 mL/min. The reaction was stirred at 85° C. for 60 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 85% yield of (XVI) and 3% yield of (XVIII).

Workup

  1. customwas established at 25° C.
  2. temperatureThe contents of the autoclave were cooled to 85° C.
  3. stirringThe reaction was stirred at 85° C. for 60 min.
  4. temperatureThen the reaction was cooled to 25° C.
  5. customremoved from the autoclave

Sources & evidence

ORD record
ord-de3993ad77a74323a11cc211b5cb9037
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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