Ethylenediaminetetraacetic Acid → Bismuth EDTA

HRID 1085047Notes

Reaction equation

HRID 1085047 reaction equation
[N+]([O-])([O-])=O.[O-2].[Bi+3:6].[CH2:7]([N:18]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][C:20]([OH:22])=[O:21])[CH2:8][N:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12]>O>[Bi:6].[CH2:8]([N:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][N:18]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 6049Ethylenediaminetetraacetic AcidHCID 9947828Bismuth;oxygen(2-);nitrate

Product 1

HCID 86618269Bismuth EDTAYield 61.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bismuth oxynitrate (20.09 g) and N,N'-1,2-ethanediylbis[N-(carboxymethyl)glycine] (EDTA; 17.57 g) in water (100 ml) was heated at 90°-95° for 2 h. The hot suspension was filtered and the residue re-heated at 90°-95° with water (4×70 ml) until almost all the solid had dissolved. On each extraction, the suspension was filtered and the strongly acidic filtrates evaporated in vacuo to approximately 70 ml. The mixture from the extractions was cooled to 18° and the precipitated solid filtered off and washed free of nitric acid with cold water, then ethanol and ether, and dried to give the title compound (18.52 g).

Workup

  1. temperaturewas heated at 90°-95° for 2 h
  2. filtrationThe hot suspension was filtered
  3. temperaturethe residue re-heated at 90°-95° with water (4×70 ml) until almost all the solid
  4. dissolutionhad dissolved
  5. extractionOn each extraction
  6. filtrationthe suspension was filtered
  7. customthe strongly acidic filtrates evaporated in vacuo to approximately 70 ml
  8. extractionThe mixture from the extractions
  9. temperaturewas cooled to 18°
  10. filtrationthe precipitated solid filtered off
  11. washwashed free of nitric acid with cold water
  12. dry with materialethanol and ether, and dried

Sources & evidence

ORD record
ord-1a0e8b25e17a4c0a8a2b69893fcf98d7
Source dataset
uspto-grants-1991_04
Patent number
US05008256

Reaction notes

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