Acetic Acid → N-acetyliminodiacetic acid

HRID 1386867Notes

Reaction equation

HRID 1386867 reaction equation
N(C(C)=O)(CNC(C)=O)CNC(C)=O.C=O.O.[C:18]([OH:21])(=[O:20])[CH3:19].N(CC(O)=O)CC(O)=O.[C:31]([NH:34][CH2:35][C:36]([OH:38])=[O:37])(=[O:33])[CH3:32]>CC(C)=O>[C:31]([N:34]([CH2:35][C:36]([OH:38])=[O:37])[CH2:19][C:18]([OH:21])=[O:20])(=[O:33])[CH3:32]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 712FormaldehydeHCID 962WaterHCID 8897Iminodiacetic acidHCID 10972AcetylglycineHCID 23599706HCID 23599706, compound

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
110 °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 (12.9 g, 0.72 mole), acetic acid (2.1 g, 0.035 mole), acetone (90 mL) and Co2(CO)8 (2.1 g, 0.006 mol) and pressurized to 3200 psi (22,069 kPa) CO:H2 (95:5) at 25° C. This mixture was heated to 110° C. for 30 min. HPLC analysis of this stream indicated a 95% yield of (XVI), 0.5% (XIV), and 4.5% (XVIII).

Workup

  1. custompressurized to 3200 psi (22,069 kPa) CO:H2 (95:5) at 25° C

Sources & evidence

ORD record
ord-98147b8d49a94b62978722b6fed91fb5
Source dataset
uspto-grants-2001_07
Patent number
US06265605B1

Reaction notes

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