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 Y
MeSH	Nitrilotriacetic+acid
ChEBI	CHEBI:44557 Y
RTECS number	AJ0175000
Beilstein Reference	1710776
Gmelin Reference	3726
Jmol-3D images	Image 1
SMILES C(C(=O)O)N(CC(=O)O)CC(=O)O
InChI InChI=1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13) N Key: MGFYIUFZLHCRTH-UHFFFAOYSA-N N InChI=1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13) Key: MGFYIUFZLHCRTH-UHFFFAOYSA-N InChI=1/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13) Key: MGFYIUFZLHCRTH-UHFFFAOYAZ
Properties
Molecular formula	C6H9NO6
Molar mass	191.14 g mol−1
N acid (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.

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