Acetic Acid → N-acetyliminodiacetic acid

HRID 1883254Notes

Reaction equation

HRID 1883254 reaction equation
[N:1]([C:12]([CH3:14])=[O:13])([CH2:7]NC(C)=O)[CH2:2]NC(C)=O.C=[O:16].[C:17]([OH:20])(=[O:19])C.COCC[O:25][CH3:26]>>[C:12]([N:1]([CH2:2][C:26]([OH:25])=[O:16])[CH2:7][C:17]([OH:20])=[O:19])(=[O:13])[CH3:14]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 80711,2-DimethoxyethaneHCID 23599706HCID 23599706, compound

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) and 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-dc5a300b7d2f4af98d323cf3358d3ca8
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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