Acetic Acid → N-acetyliminodiacetic acid

HRID 1859257Notes

Reaction equation

HRID 1859257 reaction equation
C(N)(=O)C.C=O.O.[C:8]([OH:11])(=[O:10])[CH3:9].N(CC(O)=O)CC(O)=O.[C:21]([NH:24][CH2:25][C:26]([OH:28])=[O:27])(=[O:23])[CH3:22]>COCCOC>[C:21]([N:24]([CH2:25][C:26]([OH:28])=[O:27])[CH2:9][C:8]([OH:11])=[O:10])(=[O:23])[CH3:22]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 178AcetamideHCID 712FormaldehydeHCID 962WaterHCID 8897Iminodiacetic acidHCID 10972Acetylglycine

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
125 °C

Procedure

A 300 mL autoclave was charged with acetamide (VII)(11.8 g, 0.2 mole), 95% paraformaldehyde (13.6 g, 0.43 mole), water (10.8 g, 0.60 mole), acetic acid (16.8 g, 0.28 mole, 0.19 g/mL of DME), DME (90 mL) and C2 (CO)8 (4.1 g, 0.012 mole) and pressurized to 1500 psi (10,345 kPa) CO:H2 (95:5) at 25° C. This mixture was heated to 125° C. for 30 min. HPLC analysis of this stream indicated a 91% yield of (XVI), 1% (XIV), and 3% (XVIII).

Workup

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

Sources & evidence

ORD record
ord-d2c2eaa325df40348427539c69bff99c
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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