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) 2.4H2O (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 25° 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 25° 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-91475178166c4142a8245f1a48b79648
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265605B1
Reaction notes
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