Acetic Acid → N-acetyliminodiacetic acid

HRID 1883251Notes

Reaction equation

HRID 1883251 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].C=O.O.[C:12]([OH:15])(=[O:14])[CH3:13].N(CC(O)=O)CC(O)=O>COCCOC>[C:1]([N:4]([CH2:13][C:12]([OH:15])=[O:14])[CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 962WaterHCID 8897Iminodiacetic acidHCID 10972Acetylglycine2×

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A 300 mL autoclave was charged with N-acetylglycine (XVIII)(23.4 g, 0.20 mole), 95% paraformaldehyde (6.8 g, 0.22 mole), water (6.5 g, 0.36 mole), acetic acid (16.8 g, 0.28 mole), DME (90 mL), and Co2(CO)8 (2.01 g, 0.006 mole) and pressurized to 1500 psi (10,345 kPa) CO:H2 (95:5) at 25° C. This mixture was heated to 110° C. for 30 min. HPLC analysis of this stream gave an 87% yield of (XVI), 1.0% (XIV), and 10% unreacted (XVIII).

Workup

  1. custompressurized to 1500 psi (10,345 kPa) CO:H2 (95:5) at 25° C

Sources & evidence

ORD record
ord-674f85b2bc7d47b5bddf566265f913c2
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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