Nitrilotriacetic acid

Nitrilotriacetic acid

Names
Preferred IUPAC name 2,2',2''-Nitrilotriacetic acid
Other names N,N-Bis(carboxymethyl)glycine 2-[Bis(carboxymethyl)amino]acetic acid[1] Triglycine[2]
Identifiers
CAS Number	139-13-9
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	1710776
ChEBI	CHEBI:44557
ChemSpider	8428
DrugBank	DB03040
ECHA InfoCard	100.004.869
EC Number	205-355-7
Gmelin Reference	3726
KEGG	C14695
MeSH	Nitrilotriacetic+Acid
PubChem	8758
RTECS number	AJ0175000
UN number	2811
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) Key: MGFYIUFZLHCRTH-UHFFFAOYSA-N
SMILES [o]:c(:[oH])CN(Cc(:[o]):[oH])Cc(:[o]):[oH] OC(=O)CN(CC(O)=O)CC(O)=O
Properties
Chemical formula	C6H9NO6
Molar mass	191.14 [3]
Appearance	White crystals
Melting point	246[3] °C (475 °F; 519 K)
Solubility in water	Insoluble. <0.01 g/100 mL at 23℃ [3]
Thermochemistry
Std enthalpy of formation (ΔfH^o298)	−1.3130–−1.3108 MJ mol^−1
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302, H319, H351
GHS precautionary statements	P281, P305+351+338
EU classification (DSD)	Xn
R-phrases	R22, R36, R40[3]
S-phrases	S26, S36/37/39, S45[3]
Flash point	100 °C (212 °F; 373 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.1 g kg^−1 (oral, rat)
Related compounds
Related alkanoic acids	EDTA Iminodiacetic acid EDDS
Related compounds	Triethanolamine Tris(2-aminoethyl)amine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH₂CO₂H)₃. It is a colourless solid that is used as a chelating agent, which forms coordination compounds with metal ions (chelates) such as Ca²⁺, Cu²⁺, and Fe³⁺.^[4]

Production and use

Nitrilotriacetic acid is commercially available as the free acid and as 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.^[5] NTA is also cogenerated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia coproduct.^[6]

Coordination chemistry and applications

NTA is a tripodal tetradentate trianionic ligand.^[7]

The uses of NTA are similar to those of EDTA, both being chelating agents. It is used for water softening and as a replacement to sodium and potassium triphosphate in detergents, and cleansers.

In one application, NTA as a chelating agent removes Cr, Cu, and As from wood that had been treated with chromated-copper arsenate (CCA). .^[8]

Laboratory uses

In the laboratory, this compound is 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 purification of proteins containing a tag consisting of six histidine residues at either terminus.^[9]

• NTA complexes
• 
  Three views of the structure of [Ni(NTA)(H₂O)₂]⁻.
• 
  Structure of the anion [Ca(NTA)(H₂O)₃]⁻.

Environment

In contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment. ^[5] The environmental impacts of NTA are minimal. Despite widespread use in cleaning products, the concentration in the water supply is too low to have a sizeable impact on human health or environmental quality. ^[10]

References

1. "Nitrilotriacetic Acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 13 July 2012.
2. Nitrilotriacetic acid
3. ChemBK Chemical Database http://www.chembk.com/en/chem/Nitrilotriacetic%20acid
4. NITRILOTRIACETIC ACID AND ITS SALTS, International Agency for Research on Cancer (IARC)
5. Charalampos Gousetis, Hans-Joachim Opgenorth (2005), "Nitrilotriacetic Acid", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a17_377
6. Hart, J. Roger (2005) "Ethylenediaminetetraacetic Acid and Related Chelating Agents" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_095
7. B. L. Barnett, V. A. Uchtman "Structural investigations of calcium-binding molecules. 4. Calcium binding to aminocarboxylates. Crystal structures of Ca(CaEDTA).7H2O and Na(CaNTA)" Inorg. Chem., 1979, volume 18, pp 2674–2678. doi:10.1021/ic50200a007
8. Fang-Chih, C.; Ya-Nang, W.; Pin-Jui, C.; Chun-Han, K. Factors affecting chelating extraction of Cr, Cu, and As from CCA-treated wood. J. Environ. Manag. 2013, 122.
9. qiaexpressionist
10. Brouwer, N.; Terpstra, P. Ecological and Toxicological Properties of Nitrilotriacetic Acid (NTA) as a Detergent Builder. Tenside Surfactants Detergents 1995, 32, 225-228.