Acetic Acid → N-acetyliminodiacetic acid

HRID 1859255Notes

Reaction equation

HRID 1859255 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].C=[O:6].[C:7]([OH:10])(=[O:9])[CH3:8].CO[CH2:13][CH2:14][O:15]C>>[C:1]([N:4]([CH2:13][C:14]([OH:15])=[O:6])[CH2:8][C:7]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 178AcetamideHCID 712FormaldehydeHCID 80711,2-Dimethoxyethane

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 30%

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), acetic acid (10.6 g, 0.18 mole, 0.12 g/mL of DME), DME (90 mL) and Co2 (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 30% yield of (XVI) a 47% yield of (XVIII).

Workup

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

Sources & evidence

ORD record
ord-49d758a9fade4105a24e5cd21867eaa4
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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