Acetic Acid → N-acetyliminodiacetic acid

HRID 1883252Notes

Reaction equation

HRID 1883252 reaction equation
[N:1]([C:12]([CH3:14])=[O:13])([CH2:7]NC(C)=O)[CH2:2][NH:3][C:4]([CH3:6])=[O:5].C1[CH2:19][O:18]CC1.C=[O:21].[C:22]([OH:25])(=[O:24])[CH3:23]>>[C:12]([N:1]([CH2:2][C:19]([OH:18])=[O:21])[CH2:7][C:22]([OH:25])=[O:24])(=[O:13])[CH3:14].[C:4]([NH:3][CH2:23][C:22]([OH:25])=[O:24])(=[O:5])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712Formaldehyde2×HCID 8028TetrahydrofuranHCID 23599706HCID 23599706, compound

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-2c7f37558ed048029667ce2111df473f
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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