Ethylenediaminetetraacetic Acid → Ethylenediaminetetraacetic dianhydride

HRID 2295798Notes

Reaction equation

HRID 2295798 reaction equation
[Cl-].[Ca+2].[Cl-].[CH2:4]([N:15]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][C:17]([OH:19])=O)[CH2:5][N:6]([CH2:11][C:12]([OH:14])=[O:13])[CH2:7][C:8]([OH:10])=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[O:22]=[C:21]1[O:23][C:17](=[O:19])[CH2:16][N:15]([CH2:4][CH2:5][N:6]2[CH2:7][C:8](=[O:10])[O:14][C:12](=[O:13])[CH2:11]2)[CH2:20]1

Participants

5

Reactant 3

HCID 6049Ethylenediaminetetraacetic AcidHCID 7918Acetic AnhydrideHCID 5284359Calcium Chloride

Product 1

HCID 513917Ethylenediaminetetraacetic dianhydride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 250 ml round bottomed flask fitted with a magnetic stirrer, condenser, and a drying tube (calcium chloride), was added pyridine (dried by distillation from potassium hydroxide) (80 ml). Ethylenediaminetetraacetic acid (29.12 g) was added followed by acetic anhydride (37.6 ml). The suspension was stirred and heated at 65°-80° C. for 7 hr. The mixture was cooled overnight and the white solid filtered off. The solid was washed once with pyridine (dry 20 ml) and four times with ether (dry 4×40 ml). The white solid was dried on a manifold and stored in a desiccator.

Workup

  1. temperatureheated at 65°-80° C. for 7 hr
  2. temperatureThe mixture was cooled overnight
  3. filtrationthe white solid filtered off
  4. washThe solid was washed once with pyridine (dry 20 ml) and four times with ether (dry 4×40 ml)
  5. customThe white solid was dried on a manifold
  6. customstored in a desiccator

Sources & evidence

ORD record
ord-34115d81e5e8485da3ec6658cfbf14f2
Source dataset
uspto-grants-1984_01
Patent number
US04426453

Reaction notes

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