EDTA

Chembox new
Name = EDTA
ImageFile1 = ethylenediaminetetraacetic.png ImageSize1 = 200px
ImageFile2 = EDTA-xtal-3D-balls.png ImageSize2 = 200px
ImageName2 = Ball and stick model of the EDTA molecule, in the zwitterionic form found in the solid state
ImageName = EDTA
IUPACName = 2- [2-(Bis(carboxymethyl)amino)ethyl-(carboxymethyl)amino] acetic acid
OtherNames = EDTA, H₄EDTA, Diaminoethanetetraacetic acid, Edetic acid, Edetate, Ethylenedinitrilotetraacetic acid, Versene, Ethylene diamine tetraacetic acid
Section1 = Chembox Identifiers
CASNo = 60-00-4
ChemSpiderID = 5826
PubChem = 6049
SMILES = OC(CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O)=O
RTECS = AH4025000
Section2 = Chembox Properties
Formula = C₁₀H₁₆N₂O₈
MolarMass = 292.24 g/mol
Density = 0.86 g/cm³
MeltingPt = 237-245 °C (dec.)
Section7 = Chembox Hazards
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/ED/EDTA.html External MSDS]
MainHazards = irritant
NFPA-H = 1
NFPA-F = 0 | Reactivity=0
NFPA-R =
RPhrases = R36
SPhrases = S26

EDTA is a widely used abbreviation for the chemical compound ethylenediaminetetraacetic acid (and many other names, see table). EDTA refers to the chelating agent with the formula (HO₂CCH₂)₂NCH₂CH₂N(CH₂CO₂H)₂. This amino acid is widely used to sequester di- and trivalent metal ions (Ca²⁺ and Mg²⁺ for example). EDTA binds to metals via four carboxylate and two amine groups. EDTA forms especially strong complexes with Mn(II), Cu(II), Fe(III), Pb (II) and Co(III). [cite book | last = Holleman | first = A. F. | coauthors = Wiberg, E. | title = Inorganic Chemistry | publisher = Academic Press | location = San Diego | year = 2001 | doi = | isbn = 0-12-352651-5]

ynthesis

EDTA is mostly synthesised from 1,2-diaminoethane (ethylenediamine), formaldehyde (methanal), water and sodium cyanide. [ [http://www.chm.bris.ac.uk/motm/edta/synthesis_of_edta.htm Synthesis of EDTA ] ] This yields the tetra sodium salt, which can be converted into the acidic forms by acidification. Pioneering work on the development of EDTA was undertaken by Gerold Schwarzenbach in the 1940s. [ [http://www.chm.bris.ac.uk/motm/edta/edtah.htm Edta - Motm ] ]

Isomer

EDTA exists in different standard forms under different conditions. At very low pH or very acidic condition (fully protonated)H6Y+2 forms exist while at very high pH or very basic condition (fully deprotonated) Y-4 forms are prevalent.

Nomenclature

Popular vs. chemical nomenclature

To describe EDTA and its various protonated forms, chemists use a more cumbersome but more precise acronym that distinguishes between EDTA⁴⁻, the conjugate base that is the ligand, and H₄EDTA, the precursor to that ligand.

ynonyms

EDTA is also known as H₄EDTA, diaminoethanetetraacetic acid, edetic acid, edetate, ethylenedinitrilotetraacetic acid, celon A, gluma cleanser, versene acid, nervanaid B acid, nullapon B acid, ethylene diamine tetracetic acid, tetrine acid, trilon BS, vinkeil 100, warkeelate acid, N,N'-1,2-ethanediylbis(N-(carboxymethyl)glycine)edetic acid, YD-30, Dissolvine Z.

Coordination chemistry principles

In coordination chemistry, H₄EDTA is a member of the aminocarboxylate family of ligands that includes imidodiacetic acid ("H₂IDA") and nitrilotriacetic acid ("H₃NTA"). More specialized relatives include N,N'-ethylenediaminediacetic acid ("H₂EDDA") and 1,2-diaminocyclohexane-N,N,N',N'-tetraacetic acid ("H₄CyDTA"). These ligands are all formally derived from the amino acid glycine.

H₄EDTA forms highly stable coordination compounds that are soluble in water. In these complexes, the ligand is usually either hexa- or pentadentate, EDTA⁴⁻ or HEDTA³⁻, respectively. Such complexes are chiral, and [Co(EDTA)] ⁻ has been resolved into enantiomers. [Kirchner, S. Barium (Ethylenediaminetetracetato) Cobalt(III) 4-Hydrate" Inorganic Syntheses, McGraw-Hill: New York, 1957; Vol. 5, pages 186-188.]

Uses

In 1999, the annual consumption of EDTA was equivalent to about 35,000 tons in Europe and 50,000 tons in the US.Fact|date=February 2007 The most important uses are:
* Industrial cleaning: complexation of Ca²⁺ and Mg²⁺ ions, binding of heavy metals.
* Detergents: complexation of Ca²⁺ and Mg²⁺ (reduction of water hardness).
* Photography: use of Fe(III)EDTA as oxidizing agent.
* Pulp and paper industry: complexation of heavy metals during chlorine-free bleaching, stabilization of hydrogen peroxide.
* Textile industry: complexation of heavy metals, bleach stabilizer.
* Agrochemicals: Fe, Zn and Cu fertilizer, especially in calcareous soils.
* Hydroponics: iron-EDTA is used to solubilize iron in nutrient solutions.

More specialised uses

* Food: added as preservative to prevent catalytic oxidation by metal ions or stabilizer and for iron fortification.cite journal | author=Furia T | title=EDTA in Foods — A technical review | journal=Food Technology | volume=18 | issue=12 | pages=1874–1882 | year=1964]
*Approved by the FDA as a preservative in packaged foods, vitamins, and baby food.Fact|date=August 2008
* Personal care: added to cosmetics to improve product stability.
* Oil production: added into the borehole to inhibit mineral precipitation.Fact|date=February 2007
* Dairy and beverage industry: cleaning milk stains from bottles.Fact|date=February 2007
* Flue gas cleaning: removal of NO_x.
* Soft drinks containing ascorbic acid and sodium benzoate, to mitigate formation of benzene (a carcinogen).Fact|date=February 2007
* Recycling: recovery of lead from used lead acid batteries.

Medicine

* EDTA is used in chelation therapy for acute hypercalcemia, mercury poisoning and lead poisoning [cite web | author = Ruth DeBusk "et al." | title = Ethylenediaminetetraacetic acid (EDTA) | year = 2002 | url=http://www.umm.edu/altmed/articles/ethylenediaminetetraacetic-acid-000302.htm | accessdate=2007-07-25] .
* Combined with chromium, EDTA is used to evaluate kidney function. It is administered intravenously and its filtration into the urine is monitored. This method is considered the gold standard for evaluating glomerular filtration rateFact|date=September 2008: Cr-EDTA's sole way out of the body is via glomerular filtration as it is not secreted or metabolised in any other way.
* Used as anticoagulant for blood samples
* In veterinary ophthalmology EDTA may be used as an anticollagenase to prevent the worsening of corneal ulcers in animals.
*Some laboratory studies also suggest that EDTA chelation may prevent collection of platelets ( [or plaque] which can otherwise lead to formation of blood clots and prevent blood flow) on the walls of blood vessels [such as arteries] . These ideas are theoretical, however a major clinical study of the effects of EDTA on coronary arteries is currently (2008) proceeding |http://www.clinicaltrials.gov/ct/show/NCT00044213?order=2] [3]
* Dentistry as a root canal irrigant to remove inorganic debris (smear layer) and prepare root canals for obturation.
* EDTA is used to remove excess iron from the body in the disease thalassemia, due to repeated blood transfusions.

Laboratory science

*Scavenging metal ions: in biochemistry and molecular biology, ion depletion is commonly used to inactivate metal-dependent enzymes which could damage DNA or proteins
*Complexometric titrations.
*Buffer solutions.
*Determination of water hardness.
*EDTA may be used as a masking agent to remove a metal ion which would interfere with the analysis of a second metal ion present
*An anticoagulant in medical and laboratory equipment.
*A preservative (usually to enhance the action of another preservative such as benzalkonium chloride or thiomersal) in ocular preparations and eyedrops. See "les conservateurs en opthalmologie" Doctors Patrice Vo Tan & Yves lachkar, Librarie Médicale Théa.
*A titrant used to determine nickel concentration in an electroless nickel plating bath.
*In metallography to remove staining due to etchants. Metal oxides are removed by gently swabbing with EDTA and rinsing in water.
*In cell cultures EDTA is used as a chelating agent which binds to calcium and prevents joining of cadherins between cells, preventing cell clumping. (often used in cell culture control).

Toxicity

EDTA has been found to be both cytotoxic and weakly genotoxic in laboratory animals. Oral exposures have been noted to cause reproductive and developmental effects.cite journal|author=Lanigan RS and Yamarik TA | title=Final report on the safety assessment of EDTA, calcium disodium EDTA, diammonium EDTA, dipotassium EDTA, disodium EDTA, TEA-EDTA, tetrasodium EDTA, tripotassium EDTA, trisodium EDTA, HEDTA, and trisodium HEDTA | journal=Int J Toxicol. | volume=21 Suppl 2 | pages=95–142 | year=2002 | url=http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=12396676&dopt=AbstractPlus | accessdate=2008-01-28] The same study by Lanigan also found that both dermal exposure to EDTA in most cosmetic formulations and inhalation exposure to EDTA in aerosolized cosmetic formulations would produce systemic effects below those seen to be toxic in oral dosing studies.

Environmental behavior

Widespread use of EDTA and its slow removal under many environmental conditions has led to its status as the most abundant anthropogenic compound in many European surface waters. River concentrations in Europe are reported as 10-100 μg/L, and lake concentrations are in the 1-10 μg/L range. EDTA concentrations in U.S. groundwater receiving wastewater effluent discharge have been reported at 1-72 μg/L, and EDTA was found to be an effective tracer for effluent, with higher concentrations of EDTA corresponding to a greater percentage of reclaimed water in drinking water production wells.

EDTA is not degraded or removed during conventional wastewater treatment. However, an adjustment of pH and sludge residence time can result in almost complete mineralization of EDTA. A variety of microorganisms have been isolated from water, soils, sediments and sludges that are able to completely mineralize EDTA as a sole source of carbon, nitrogen and energy.

Recalcitrant chelating agents such as EDTA are an environmental concern predominantly because of their persistence and strong metal chelating properties. The presence of chelating agents in high concentrations in wastewaters and surface waters has the potential to remobilize heavy metals from river sediments and treated sludges, although low and environmentally relevant concentrations seem to have only a very minor influence on metal solubility. Low concentrations of chelating agents may either stimulate or decrease plankton or algae growth, while high concentrations always inhibit activity. Chelating agents are nontoxic to many forms of life on acute exposure; the effects of longer-term low-level exposure are unknown. EDTA at elevated concentrations is toxic to bacteria due to chelation of metals in the outer membrane. EDTA ingestion at high concentrations by mammals changes excretion of metals and can affect cell membrane permeability.

Methods of detection and analysis

The most sensitive method of detecting and measuring EDTA in biological samples is selected-reaction-monitoring capillary-electrophoresis mass-spectrometry (abbreviation SRM-CE/MS) which has a detection limit of 7.3 ng/mL in human plasma and a quantitation limit of 15 ng/mL.cite journal | author = Robin L. Sheppard, and Jack Henion | title = Determining EDTA in Blood | journal = Analytical Chemistry | volume = 69 | pages = 477A–480A | year = 1997 | url=http://pubs.acs.org/hotartcl/ac/97/aug/det.html|accessdate=2007-07-25 |format= |work= ] This method works with sample volumes as small as ~7-8 nL.

EDTA has also been measured in non-alcoholic beverages using high performance liquid chromatography (HPLC) which has a detection limit of 0.6 μg/mL and a quantitation limit of 2.0 μg/mL. [cite journal | author = S. Loyaux-Lawniczak, J. Douch, and P. Behra | title = Optimisation of the analytical detection of EDTA by HPLC in natural waters | journal = Fresenius' J. Anal. Chem. | volume = 364 | issue = 8 | pages = 727–731 | issn = 0937-0633 | year = 1999 | url=http://cat.inist.fr/?aModele=afficheN&cpsidt=1898737|accessdate=2007-07-25 |format= |work=
doi = 10.1007/s002160051422] [cite journal | author = Carolina E. Cagnassoa, Laura B. López, Viviana G.Rodríguez and Mirta E. Valencia | title = Development and validation of a method for the determination of EDTA in non-alcoholic drinks by HPLC | journal = Journal of Food Composition and Analysis | volume = 20 | issue = 3-4 | month = May | year = 2006 | doi=10.1016/j.jfca.2006.05.008 | accessdate = 2007-07-25 | pages = 248]

Forensics

* EDTA played a role in the O.J. Simpson trial when one of the blood samples collected from Simpson's estate was found to contain traces of the compound. This was used by the defense to indicate that the sample had been planted from one of the vials collected during the investigation. Prosecution claimed EDTA might have appeared in the sample as a result of eating McDonald's foods (either through bloodstream or, more likely, via contamination of blood flowing over the hand used in grabbing the food)Fact|date=May 2008.

ee also

* DMPS
* DMSA
* DTPA
* EGTA
* Heavy metal poisoning
* Lead poisoning
* Mercury poisoning
* NTA
* Phosphonate

References

Endnotes

Notations

* A Textbook on EDTA Chelation Therapy, Linus Pauling, Hampton Roads Publishing, Charlottsville, VA

External links

*
* [http://www.theoprax-research.com/pool.html pH-Spectrum of EDTA complexes]
* [http://www.chm.bris.ac.uk/motm/edta/edtah.htm EDTA: Molecule of the Month]
* [http://www.chem.utk.edu/~chem319/Experiments/Exp6.pdf EDTA Determination of Total Water Hardness]
* [http://www.gordonresearch.com/articles_oral_chelation/oral_edta_references/references.html 507 references regarding oral EDTA]