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EDTA

Ethylenediaminetetraacetic acid
Skeletal formula of ethylenediaminetetraacetic acid
EDTA di-sodium salt
Disodium EDTA
Names
Systematic IUPAC name
2,2',2'',2'''-(Ethane-1,2-diyldinitrilo)tetraacetic acid
Other names
  • N,N'-Ethane-1,2-diylbis[N-( carboxymethyl)glycine]
  • Fiaminoethane-tetraacetic acid
  • Edetic acid (conjugate base edetate) (INN, USAN)
  • Ethylenedinitrilo-tetraacetic acid
  • Versene
Identifiers
60-00-4 YesY
3D model (Jmol) Interactive image
Abbreviations EDTA, H4EDTA
1716295
ChEBI CHEBI:42191 YesY
ChEMBL ChEMBL858 YesY
ChemSpider 5826 YesY
DrugBank DB00974 YesY
ECHA InfoCard 100.000.482
EC Number 200-449-4
144943
KEGG D00052 YesY
MeSH Edetic+Acid
PubChem 6049
RTECS number AH4025000
UNII 9G34HU7RV0 YesY
UN number 3077
Properties
C10H16N2O8
Molar mass 292.24 g·mol−1
Appearance Colourless crystals
Density 860 mg mL−1 (at 20 °C)
log P −0.836
Acidity (pKa) 1.782
Basicity (pKb) 12.215
Thermochemistry
−1.7654 to −1.7580 MJ mol−1
−4.4617 to −4.4545 MJ mol−1
Pharmacology
S01XA05 (WHO) V03AB03 (WHO) (salt)
  • Intramuscular
  • Intravenous
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H319
P305+351+338
Irritant Xi
R-phrases R36
S-phrases (S2), S26
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1000 mg/kg (oral, rat)
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Ethylenediaminetetraacetic acid (EDTA), also known by several other names, is a chemical used for both industrial and medical purposes.

It is an aminopolycarboxylic acid and a colourless, water-soluble solid. Its conjugate base is ethylenediaminetetraacetate. It is widely used to dissolve limescale. Its usefulness arises because of its role as a hexadentate ("six-toothed") ligand and chelating agent, i.e., its ability to "sequester" metal ions such as Ca2+ and Fe3+. After being bound by EDTA into a metal complex, metal ions remain in solution but exhibit diminished reactivity. EDTA is produced as several salts, notably disodium EDTA and calcium disodium EDTA.

In industry, EDTA is mainly used to sequester metal ions in aqueous solution. In the textile industry, it prevents metal ion impurities from modifying colors of dyed products. In the pulp and paper industry, EDTA inhibits the ability of metal ions, especially Mn2+, from catalyzing the disproportionation of hydrogen peroxide, which is used in "chlorine-free bleaching". In a similar manner, EDTA is added to some food as a preservative or stabilizer to prevent catalytic oxidative decoloration, which is catalyzed by metal ions. In soft drinks containing ascorbic acid and sodium benzoate, EDTA mitigates formation of benzene (a carcinogen).

The reduction of water hardness in laundry applications and the dissolution of scale in boilers both rely on EDTA and related complexants to bind Ca2+, Mg2+, as well as other metal ions. Once bound to EDTA, these metal centers tend not to form precipitates or to interfere with the action of the soaps and detergents. For similar reasons, cleaning solutions often contain EDTA.


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