Acetic Acid → N-acetyliminodiacetic acid

HRID 1859258Notes

Reaction equation

HRID 1859258 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]>CC(C)=O>[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 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-d195abf519d1403cb215e600a8ab3708
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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