Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Nitrilotriacetic acid: Difference between pages

{{chembox

| Watchedfields = changed

| verifiedrevid = 462261723

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 160

| ImageName = Skeletal formula of nitrilotriacetic acid

| PIN = 2,2′,2′′-Nitrilotriacetic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 21, 679 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4| last1 = Favre | first1 = Henri A. | last2 = Powell | first2 = Warren H. }}</ref>

| OtherNames = ''N'',''N''-Bis(carboxymethyl)glycine<br />2-[Bis(carboxymethyl)amino]acetic acid<ref name="pc1">{{cite web|title=Nitrilotriacetic Acid - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8758&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=13 July 2012|location=USA|date=26 March 2005|at=Identification}}</ref><br />Triglycine<ref>[http://www.chemspider.com/8428 Nitrilotriacetic acid]</ref> Trilon

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo_Comment = (free acid)

| CASNo2 = 5064-31-3

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2_Comment = (trisodium salt)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KA90006V9D

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = E3C8R2M0XD

| UNII1_Comment = (trisodium salt)

| PubChem = 8758

| ChemSpiderID = 8428

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 205-355-7

| UNNumber = 2811

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| KEGG = C14695

| KEGG_Ref = {{keggcite|changed|kegg}}

| MeSHName = Nitrilotriacetic+Acid

| ChEBI_Ref = {{ebicite|correct|EBI}}

| RTECS = AJ0175000

| Beilstein = 1710776

| Gmelin = 3726

| SMILES = O=C(O)CN(CC(=O)O)CC(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|Section2={{Chembox Properties

| C=6 | H=9 | N=1 | O=6

| MolarMass = 191.14 <ref name=ChemBK />

| MeltingPtC = 246 <ref name=ChemBK />

| Solubility = Insoluble. <0.01 g/100 mL at 23°C <ref name=ChemBK />

| Appearance = White crystals

}}

|Section3={{Chembox Thermochemistry

| DeltaHf = −1.3130–−1.3108 MJ mol⁻¹

}}

|Section4={{Chembox Hazards

| GHSPictograms = {{gHS exclamation mark}} {{gHS health hazard}}

| GHSSignalWord = '''WARNING'''

| HPhrases = {{h-phrases|302|319|351}}

| PPhrases = {{p-phrases|281|305+351+338}}

| FlashPtC = 100

| LD50 = 1.1 g kg⁻¹ <small>(oral, rat)</small>

}}

|Section5={{Chembox Related

| OtherFunction_label = alkanoic acids

| OtherFunction = {{unbulleted list|[[EDTA]]|[[Iminodiacetic acid]]|[[EDDS]]}}

| OtherCompounds = {{unbulleted list|[[Triethanolamine]]|[[Tris(2-aminoethyl)amine]]}}

}}

}}

'''Nitrilotriacetic acid''' (NTA) is the [[aminopolycarboxylic acid]] with the formula N(CH₂CO₂H)₃. It is a colourless solid. Its conjugate base '''nitrilotriacetate''' is used as a [[chelating agent]] for Ca²⁺, Co²⁺, Cu²⁺, and Fe³⁺.<ref>[http://www.inchem.org/documents/iarc/vol48/48-12.html Nitrilotriacetic Acid and Its Salts], International Agency for Research on Cancer</ref>

==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.<ref name = Ullmann>{{Ullmann | year=2022|doi = 10.1002/14356007.a17_377.pub3 | title = Nitrilotriacetic Acid | author = Thomas Schmidt, Charalampos Gousetis, Hans-Joachim Opgenorth}}</ref> NTA is also cogenerated as an impurity in the synthesis of [[EDTA]], arising from reactions of the ammonia coproduct.<ref name="Ullmann/Roger">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}}</ref> Older routes to NTA included alkylation of ammonia with chloroacetic acid and oxidation of [[triethanolamine]].

==Coordination chemistry and applications==

The conjugate base of NTA is a [[Tripodal ligand|tripodal]] [[Tetradentate ligand|tetradentate]] trianionic ligand, forming [[coordination compound]]s with a variety of metal ions.<ref>{{cite journal|author=B. L. Barnett, V. A. Uchtman|title=Structural Investigations of Calcium-Binding Molecules. 4. Calcium Binding to Aminocarboxylates. Crystal Structures of Ca(CaEDTA)^.7H₂O and Na(CaNTA)|journal=Inorg. Chem.|year=1979|volume=18|issue=10 |pages=2674–2678|doi=10.1021/ic50200a007}}</ref>

Like [[EDTA]], its sodium salt is used for [[water softening]] to remove Ca²⁺. For this purpose, NTA is a replacement for [[triphosphate]], which once was widely used in detergents, and cleansers, but can cause [[eutrophication]] of lakes.

In one application, sodium NTA removes Cr, Cu, and As from wood that had been treated with [[chromated copper arsenate]].<ref>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.</ref>

===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 [[Polyhistidine-tag|His-tag]] method.<ref>{{cite journal|last1=Liu|first1=Weijing|title=Layer-by-Layer Deposition with Polymers Containing Nitrilotriacetate, A Convenient Route to Fabricate Metal- and Protein-Binding Films|journal=ACS Applied Materials & Interfaces|date=2016|volume=8|issue=16|pages=10164–73|doi=10.1021/acsami.6b00896|pmid=27042860}}</ref> The modified NTA is used to immobilize [[nickel]] on a solid support. This allows purification of proteins containing a tag consisting of six histidine residues at either terminus.<ref>[http://www1.qiagen.com/literature/handbooks/PDF/Protein/Expression/QXP_QIAexpressionist/1024473_QXPHB_0603.pdf qiaexpressionist]</ref>

The His-tag binds the metal of metal [[Chelation|chelator]] complexes. Previously, [[iminodiacetic acid]] was used for that purpose. Now, nitrilotriacetic acid is more commonly used.<ref>{{Cite journal|last1=Lauer|first1=Sabine A.|last2=Nolan|first2=John P.|date=2002|title=Development and characterization of Ni-NTA-bearing microspheres|journal=Cytometry|volume=48|issue=3|pages=136–145|doi=10.1002/cyto.10124|pmid=12116359|issn=1097-0320|doi-access=free}}</ref>

For laboratory uses, Ernst Hochuli et al. (1987) coupled the NTA ligand and nickel ions to [[agarose]] beads.<ref>{{Cite journal|last1=Hochuli|first1=E.|last2=Döbeli|first2=H.|last3=Schacher|first3=A.|date=January 1987|title=New metal chelate adsorbent selective for proteins and peptides containing neighbouring histidine residues|journal=Journal of Chromatography A|volume=411|pages=177–184|doi=10.1016/s0021-9673(00)93969-4|pmid=3443622|issn=0021-9673}}</ref> This [https://cube-biotech.com/products/purification-resins/his-affinity-resins/ni-nta-agarose/ Ni-NTA Agarose] is the most used tool to purify His-tagged proteins via affinity chromatography.

<gallery mode="packed" caption="NTA complexes" widths="500px" heights="100px" perrow="2">

Ni(NTA)(aq)23views.png|Three views of the structure of [Ni(NTA)(H₂O)₂]⁻.

File:Calcium complex of NTA trianion.svg|Structure of the nitrilotriacetate anion [Ca(NTA)(H₂O)₃]⁻.

</gallery>

==Toxicity and environment==

In contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment.<ref name=Ullmann/> 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.<ref>Brouwer, N.; Terpstra, P. Ecological and Toxicological Properties of Nitrilotriacetic Acid (NTA) as a Detergent Builder. Tenside Surfactants Detergents 1995, 32, 225-228.</ref>

==Related compounds==

* [[N-Methyliminodiacetic acid]] (MIDA), the N-methyl derivative of IDA

* [[Imidodiacetic acid]], the amino diacetic acid

* [[N-(2-Carboxyethyl)iminodiacetic acid]], a more biodegradable analogue of NTA

* N-hydroxyiminodiacetic acid (HIDA), {{chem2|HON(CH2CO2H)2}} ([[registry number]] = 87339-38-6)<ref>{{cite journal |doi=10.1002/ejoc.200601053 |title=Stabilizing Factors for Vanadium(IV) in Amavadin |date=2007 |last1=Hubregtse |first1=Ton |last2=Hanefeld |first2=Ulf |last3=Arends |first3=Isabel W. C. E. |journal=European Journal of Organic Chemistry |volume=2007 |issue=15 |pages=2413–2422 }}</ref> See [[HIDA scan]].

==References==

{{reflist|refs=<ref name=ChemBK>ChemBK Chemical Database http://www.chembk.com/en/chem/Nitrilotriacetic%20acid</ref>}}

{{Authority control}}

[[Category:Amines]]

[[Category:Acetic acids]]

[[Category:Chelating agents]]

[[Category:IARC Group 2B carcinogens]]

[[Category:Tripodal ligands]]