Acetic Acid → Iminodiacetic acid
Reaction equation
NC(N)=O.C=O.[NH2:7][CH2:8][C:9]([OH:11])=[O:10].[C:12]([OH:15])(=[O:14])[CH3:13]>>[NH:7]([CH2:13][C:12]([OH:15])=[O:14])[CH2:8][C:9]([OH:11])=[O:10]Participants
Conditions
- Temperature
- 130 °C
Procedure
A 2 L autoclave was charged with urea (V)(60 g, 1.0 mole), Co(OAc)2 ·4H2 (66 g, 0.26 mole), and acetic acid (1 L). 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 one hour, rapid gas uptake was observed. The reaction mass was cooled to 85° C. and the feed gas was changed to a CO:H2 (90:10) composition. Under a constant 3200 psi (22,069 kPa), 47 Wt. % formalin (320 mL, 5.28 mole) was delivered at 16 mL/min. The reaction was stirred at 85° C. for 90 min. after the formalin addition was complete. Then the reaction was cooled to 250° C., removed from the autoclave, and concentrated to an oil under reduced pressure. The oil was treated with 2 L of 10% HCl at 100° C. for two hours. This resulted in a 13% yield of (XIV) and 5% glycine.
Workup
- customwas established at 25° C.
- temperatureThe reaction mass was cooled to 85° C.
- stirringThe reaction was stirred at 85° C. for 90 min.
- temperatureThen the reaction was cooled to 250° C.
- customremoved from the autoclave
- concentrationconcentrated to an oil under reduced pressure
- additionThe oil was treated with 2 L of 10% HCl at 100° C. for two hours
Sources & evidence
- ORD record
- ord-a54454cb2e02419c9e03685b64ee30f2
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06153753
Reaction notes
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