Nitrilotriacetic acid

Nitrilotriacetic acid
Preferred IUPAC name

2,2',2''-Nitrilotriacetic acid
Systematic name

2-[Bis(carboxymethyl)amino]acetic acid
Other names

Triglycine
Identifiers
CAS number 139-13-9 Y, 15934-02-8 (monoammoniate), 71264-32-9 (diammoniate)
PubChem 8758 Y, 61821 (monoammoniate) Y, 62259 (diammoniate) Y, 16219712 (monosodium), 23617736 (monocalcium) Y
ChemSpider 8428 Y, 55699 (monoammoniate) Y, 56063 (diammoniate) Y, 17347029 (monosodium) Y, 19954700 (monocalcium) Y
EC number 205-355-7
UN number 2811
DrugBank DB03040
KEGG C14695 N
MeSH Nitrilotriacetic+acid
ChEBI CHEBI:44557 Y
RTECS number AJ0175000
Beilstein Reference 1710776
Gmelin Reference 3726
Jmol-3D images Image 1
Properties
Molecular formula C6H9NO6
Molar mass 191.14 g mol−1
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nitrilotriacetic acid (NTA), C6H9NO6, is a polyamino carboxylic acid and is used as a chelating agent which forms coordination compounds with metal ions (chelates) such as Ca2+, Cu2+ or Fe3+.[1]

The uses of NTA are similar to that of EDTA. However, in contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment.

Contents

Production

This compound is commercially available as the free acid and the sodium salt. It is produced from ammonia, formaldehyde, and sodium cyanide or hydrogen cyanide. Worldwide capacity is estimated at 100 thousand tonnes per year.[2]

Uses

Nitrilotriacetic acid is a chelating agent. It is used for water softening and as a replacement to sodium triphosphate in detergents, and potassium triphosphate in cleansers.[2]

In the laboratory, this compound may be used in complexometric titrations. A variant of NTA is used for protein isolation and purification in the His-tag method. The modified NTA is used to immobilize nickel to a solid support. This allows separation of proteins containing "tag" containing six histidine residues at the C-terminus.[3]

Biodegradation

Nitrilotriacetic acid is easily biodegraded; 98 % is removed in biological wastewater treatment plants.[2]

References

  1. ^ NITRILOTRIACETIC ACID AND ITS SALTS, International Agency for Research on Cancer (IARC)
  2. ^ a b c Charalampos Gousetis, Hans-Joachim Opgenorth (2005), "Nitrilotriacetic Acid", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a17_377 
  3. ^ qiaexpressionist