Ethylenediamine → Ethylenediaminediacetic acid

HRID 1418832Notes

Reaction equation

HRID 1418832 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].Cl[CH2:6][C:7]([O-:9])=[O:8].[Na+]>O>[C:7]([CH2:6][NH:3][CH2:2][CH2:1][NH:4][CH2:6][C:7]([OH:9])=[O:8])([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 23665759Sodium chloroacetate

Product 1

HCID 61975Ethylenediaminediacetic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a four-necked flask containing ethylenediamine (3 g, 0.05 mol) and water (50 g), an aqueous sodium chloroacetate solution (11.7 g, 0.1 mol) was added dropwise over 30 minutes. The contents were mixed at 60° C. for 2 hours, and then washed with ethanol to give 8.8 g of N,N'-bis(carboxymethyl)ethylenediamine (separation yield: 88 wt %).

Workup

  1. additionThe contents were mixed at 60° C. for 2 hours
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-caf0f8b02ed34a438956b058f41492d2
Source dataset
uspto-grants-1999_03
Patent number
US05885955

Reaction notes

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