Acetic Acid → N-acetyliminodiacetic acid

HRID 1859252Notes

Reaction equation

HRID 1859252 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-0f497cb98fdb4c079d191efcdef0a202
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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