Nitrilotriacetic acid

Last updated
Nitrilotriacetic acid
Nitrilotriacetic-acid-2D-skeletal.png
Names
Preferred IUPAC name
2,2′,2′′-Nitrilotriacetic acid [1]
Other names
N,N-Bis(carboxymethyl)glycine
2-[Bis(carboxymethyl)amino]acetic acid [2]
Triglycine [3] Trilon
Identifiers
3D model (JSmol)
1710776
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.004.869 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-355-7
3726
KEGG
MeSH Nitrilotriacetic+Acid
PubChem CID
RTECS number
  • AJ0175000
UNII
UN number 2811
  • 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) Yes check.svgY
    Key: MGFYIUFZLHCRTH-UHFFFAOYSA-N Yes check.svgY
  • O=C(O)CN(CC(=O)O)CC(=O)O
Properties
C6H9NO6
Molar mass 191.14 [4]
AppearanceWhite crystals
Melting point 246 [4]  °C (475 °F; 519 K)
Insoluble. <0.01 g/100 mL at 23°C [4]
Thermochemistry
−1.3130–−1.3108 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H302, H319, H351
P281, P305+P351+P338
Flash point 100 °C (212 °F; 373 K)
Lethal dose or concentration (LD, LC):
1.1 g kg−1(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).
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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+. [5]

Contents

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. [6] NTA is also cogenerated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia coproduct. [7] 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 tetradentate trianionic ligand, forming coordination compounds with a variety of metal ions. [8]

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. [9]

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. [10] 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. [11]

The his-tag binds the metal of metal chelator complexes. Previously, iminodiacetic acid was used for that purpose. Now, nitrilotriacetic acid is more commonly used. [12]

For laboratory uses Ernst Hochuli et al. 1987 coupled the NTA ligand and Nickel-ions to agarose beads. [13] This Ni-NTA Agarose is the most used tool to purify his tagged proteins via affinity chromatography.

Toxicity and environment

In contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment. [6] 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. [14]

Related Research Articles

<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

Chelation is a type of bonding of ions and the molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds, but this is not a necessity.

<span class="mw-page-title-main">Ethylenediaminetetraacetic acid</span> Chemical compound

Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid after its own abbreviation, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. This white, water-insoluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH. It is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble. EDTA is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.

<span class="mw-page-title-main">His-tag</span> Molecular biology technique

A polyhistidine-tag, best known by the trademarked name His-tag, is an amino acid motif in proteins that typically consists of at least six histidine (His) residues, often at the N- or C-terminus of the protein. It is also known as a hexa histidine-tag, 6xHis-tag, or His6 tag. The tag was invented by Roche, although the use of histidines and its vectors are distributed by Qiagen. Various purification kits for histidine-tagged proteins are commercially available from multiple companies.

<span class="mw-page-title-main">Imidazole</span> Chemical compound

Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.

Affinity chromatography is a method of separating a biomolecule from a mixture, based on a highly specific macromolecular binding interaction between the biomolecule and another substance. The specific type of binding interaction depends on the biomolecule of interest; antigen and antibody, enzyme and substrate, receptor and ligand, or protein and nucleic acid binding interactions are frequently exploited for isolation of various biomolecules. Affinity chromatography is useful for its high selectivity and resolution of separation, compared to other chromatographic methods.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">EDDS</span> Chemical compound

Ethylenediamine-N,N'-disuccinic acid (EDDS) is an aminopolycarboxylic acid. It is a colourless solid that is used as chelating agent that may offer a biodegradable alternative to EDTA, which is currently used on a large scale in numerous applications.

<span class="mw-page-title-main">Cleaning agent</span> Substance used to remove dirt or other contaminants

Cleaning agents or hard-surface cleaners are substances used to remove dirt, including dust, stains, foul odors, and clutter on surfaces. Purposes of cleaning agents include health, beauty, removing offensive odor, and avoiding the spread of dirt and contaminants to oneself and others. Some cleaning agents can kill bacteria and clean at the same time. Others, called degreasers, contain organic solvents to help dissolve oils and fats.

<span class="mw-page-title-main">Iminodiacetic acid</span> Chemical compound

Iminodiacetic acid is the organic compound with the formula HN(CH2CO2H)2, often abbreviated to IDA. A white solid, the compound is a dicarboxylic acid amine (the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). The iminodiacetate dianion is a tridentate ligand, forming metal complexes by forming two, fused, five membered chelate rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100. Complexes of IDA and EDTA were introduced in the early 1950's by Schwarzenbach.

<span class="mw-page-title-main">Aminopolycarboxylic acid</span>

An aminopolycarboxylic acid is a chemical compound containing one or more nitrogen atoms connected through carbon atoms to two or more carboxyl groups. Aminopolycarboxylates that have lost acidic protons form strong complexes with metal ions. This property makes aminopolycarboxylic acids useful complexone in a wide variety of chemical, medical, and environmental applications.

<span class="mw-page-title-main">DOTA (chelator)</span> Chemical compound

DOTA (also known as tetraxetan) is an organic compound with the formula (CH2CH2NCH2CO2H)4. The molecule consists of a central 12-membered tetraaza (i.e., containing four nitrogen atoms) ring. DOTA is used as a complexing agent, especially for lanthanide ions. Its complexes have medical applications as contrast agents and cancer treatments.

Wastewater comes out of the laundry process with additional energy (heat), lint, soil, dyes, finishing agents, and other chemicals from detergents. Some laundry wastewater goes directly into the environment, due to the flaws of water infrastructure. The majority goes to sewage treatment plants before flowing into the environment. Some chemicals remain in the water after treatment, which may contaminate the water system. Some have argued they can be toxic to wildlife, or can lead to eutrophication.

<span class="mw-page-title-main">2,2',2''-Nitrilotriacetonitrile</span> Chemical compound

Nitrilotriacetonitrile (NTAN) is a precursor for nitrilotriacetic acid, for tris(2-aminoethyl)amine and for the epoxy resin crosslinker aminoethylpiperazine.

<span class="mw-page-title-main">Tetrasodium iminodisuccinate</span> Chemical compound

Tetrasodium iminodisuccinate is a sodium salt of iminodisuccinic acid, also referred to as N-(1,2-dicarboxyethyl)aspartic acid.

<i>N</i>-(2-Carboxyethyl)iminodiacetic acid Chemical compound

N-(2-Carboxyethyl)iminodiacetic acid or β-ADA(β-alanine diacetate) is an organic compound with the formula HO2CCH2CH2N(CH2CO2H)2. It is a white solid. The compound is classified as an aminocarboxylic acid, formally a derivative of glycine.

<span class="mw-page-title-main">Trisodium dicarboxymethyl alaninate</span> Chemical compound

Trisodium N-(1-carboxylatoethyl)iminodiacetate, methylglycinediacetic acid trisodium salt (MGDA-Na3) or trisodium α-DL-alanine diacetate (α-ADA), is the trisodium anion of N-(1-carboxyethyl)iminodiacetic acid and a tetradentate complexing agent. It forms stable 1:1 chelate complexes with cations having a charge number of at least +2, e.g. the "hard water forming" cations Ca2+ or Mg2+. α-ADA is distinguished from the isomeric β-alaninediacetic acid by better biodegradability and therefore improved environmental compatibility.

Transition metal amino acid complexes are a large family of coordination complexes containing the conjugate bases of the amino acids, the 2-aminocarboxylates. Amino acids are prevalent in nature, and all of them function as ligands toward the transition metals. Not included in this article are complexes of the amides and ester derivatives of amino acids. Also excluded are the polyamino acids including the chelating agents EDTA and NTA.

Chelated platinum is an ionized form of platinum that forms two or more bonds with a counter ion. Some platinum chelates are claimed to have antimicrobial activity.

N-Methyliminodiacetic acid is an organic compound with the formula CH3N(CH2CO2H)2. It is a white solid, which as its conjugate base CH3N(CH2CO−2)2 is used as a chelating agent for iron. It is a component of organoboron reagents as well.

References

  1. Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. pp. 21, 679. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. "Nitrilotriacetic Acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 13 July 2012.
  3. Nitrilotriacetic acid
  4. 1 2 3 ChemBK Chemical Database http://www.chembk.com/en/chem/Nitrilotriacetic%20acid
  5. Nitrilotriacetic Acid and Its Salts, International Agency for Research on Cancer
  6. 1 2 Thomas Schmidt, Charalampos Gousetis, Hans-Joachim Opgenorth (2022). "Nitrilotriacetic Acid". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_377.pub3. ISBN   978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  7. 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
  8. B. L. Barnett, V. A. Uchtman (1979). "Structural Investigations of Calcium-Binding Molecules. 4. Calcium Binding to Aminocarboxylates. Crystal Structures of Ca(CaEDTA).7H2O and Na(CaNTA)". Inorg. Chem. 18 (10): 2674–2678. doi:10.1021/ic50200a007.
  9. 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.
  10. Liu, Weijing (2016). "Layer-by-Layer Deposition with Polymers Containing Nitrilotriacetate, A Convenient Route to Fabricate Metal- and Protein-Binding Films". ACS Applied Materials & Interfaces. 8 (16): 10164–73. doi:10.1021/acsami.6b00896. PMID   27042860.
  11. qiaexpressionist
  12. Lauer, Sabine A.; Nolan, John P. (2002). "Development and characterization of Ni-NTA-bearing microspheres". Cytometry. 48 (3): 136–145. doi: 10.1002/cyto.10124 . ISSN   1097-0320. PMID   12116359.
  13. Hochuli, E.; Döbeli, H.; Schacher, A. (January 1987). "New metal chelate adsorbent selective for proteins and peptides containing neighbouring histidine residues". Journal of Chromatography A. 411: 177–184. doi:10.1016/s0021-9673(00)93969-4. ISSN   0021-9673. PMID   3443622.
  14. Brouwer, N.; Terpstra, P. Ecological and Toxicological Properties of Nitrilotriacetic Acid (NTA) as a Detergent Builder. Tenside Surfactants Detergents 1995, 32, 225-228.
  15. Hubregtse, Ton; Hanefeld, Ulf; Arends, Isabel W. C. E. (2007). "Stabilizing Factors for Vanadium(IV) in Amavadin". European Journal of Organic Chemistry. 2007 (15): 2413–2422. doi:10.1002/ejoc.200601053.