Acetic Acid → N-acetyliminodiacetic acid

HRID 1386861Notes

Reaction equation

HRID 1386861 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-0f4c9a912a7748068cc0ade26ae4c461
Source dataset
uspto-grants-2001_07
Patent number
US06265605B1

Reaction notes

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