Wikipedia

Ethylenediaminetetraacetic acid

(Redirected fromEDTA)
This article is about the chemical. For the medication, seeSodium calcium edetate.
"EDTA" redirects here. For other uses, seeEDTA (disambiguation).
"Versene" redirects here. Not to be confused withVersine.

Ethylenediaminetetraacetic acid(EDTA), also calledEDTA acidafter its own abbreviation, is anaminopolycarboxylic acidwith 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-solublecomplexeseven 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, notablydisodium EDTA,sodium calcium edetate,andtetrasodium EDTA,but these all function similarly.[4]

Ethylenediaminetetraacetic acid
3-dimensional formula of ethylenediaminetetraacetic acid
Names
IUPAC name
N,N′-(Ethane-1,2-diyl)bis[N-(carboxymethyl)glycine][1]
Systematic IUPAC name
2,2′,2′′,2′′′-(Ethane-1,2-diyldinitrilo)tetraacetic acid[1]
Other names
  • EthyleneDiamineTetraAcetic acid
  • Diaminoethane-tetraacetic acid
  • Edetic acid (conjugate baseedetate) (INN,USAN)
  • Versene
Identifiers
3D model (JSmol)
Abbreviations EDTA, H4EDTA
1716295
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.409Edit this at Wikidata
EC Number
  • 200-449-4
144943
KEGG
MeSH Edetic+Acid
RTECS number
  • AH4025000
UNII
UN number 3077
  • InChI=1S/C10H16N2O8/c13-7(14)3-11(4-8(15)16)1-2-12(5-9(17)18)6-10(19)20/h1-6H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)checkY
    Key: KCXVZYZYPLLWCC-UHFFFAOYSA-NcheckY
  • OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O
Properties
C10H16N2O8
Molar mass 292.244g·mol−1
Appearance Colourless crystals
Density 0.860 g cm−3(at 20 °C)
logP −0.836
Acidity(pKa) 2.0, 2.7, 6.16, 10.26[2]
Thermochemistry
−1765.4 to −1758.0 kJ mol−1
−4461.7 to −4454.5 kJ mol−1
Pharmacology
S01XA05(WHO)V03AB03(WHO) (salt)
  • Intramuscular
  • Intravenous
Hazards
GHSlabelling:
GHS07: Exclamation mark
Warning
H319
P305+P351+P338
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Lethal doseor concentration (LD, LC):
1000 mg/kg (oral, rat)[3]
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Uses

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Textiles and paper

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In industry, EDTA is mainly used tosequester(bind or confine) metal ions in aqueous solution. In thetextile industry,it prevents metal ion impurities from modifying colours of dyed products. In thepulp and paper industry,EDTA inhibits the ability of metal ions, especiallyMn2+,from catalysing thedisproportionationofhydrogen peroxide,which is used inchlorine-free bleaching.

Food

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In a similar manner, EDTA is added to some food as apreservativeor stabiliser to prevent catalytic oxidative decolouration, which is catalysed by metal ions.[5]

Water softener

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The reduction of water hardness in laundry applications and the dissolution of scale in boilers both rely on EDTA and relatedcomplexantsto bindCa2+,Mg2+,as well as other metal ions. Once bound to EDTA, these metal complexes are less likely to form precipitates or to interfere with the action of thesoapsanddetergents.[citation needed]For similar reasons, cleaning solutions often contain EDTA. In a similar manner EDTA is used in the cement industry for the determination of freelimeand freemagnesiain cement andclinkers.[6][page needed]

The solubilisation ofFe3+ions at or below near neutralpHcan be accomplished using EDTA. This property is useful inagricultureincluding hydroponics. However, given the pH dependence of ligand formation, EDTA is not helpful for improving iron solubility in above neutral soils.[7]Otherwise, at near-neutral pH and above, iron(III) forms insoluble salts, which are lessbioavailableto susceptible plant species.

Scrubbing

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Aqueous [Fe(EDTA)]−is used for removing ( "scrubbing")hydrogen sulfidefrom gas streams. This conversion is achieved by oxidising the hydrogen sulfide to elemental sulfur, which is non-volatile:

2 [Fe(EDTA)]−+H2S→ 2 [Fe(EDTA)]2−+S+ 2 H+

In this application, the iron(III) centre isreducedto its iron(II) derivative, which can then be reoxidised by air. In similar manner,nitrogen oxidesare removed from gas streams using [Fe(EDTA)]2−.

The oxidising properties of [Fe(EDTA)]−are also exploited inphotography,where it is used to solubilisesilverparticles.[4]

Ion-exchange chromatography

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EDTA was used in separation of thelanthanide metalsbyion-exchange chromatography.Perfected by F. H. Speddinget al.in 1954, the method relies on the steady increase instability constantof the lanthanide EDTA complexes withatomic number.[8]Usingsulfonatedpolystyrenebeads andCu2+as a retaining ion, EDTA causes the lanthanides to migrate down the column of resin while separating into bands of pure lanthanides. The lanthanides elute in order of decreasing atomic number. Due to the expense of this method, relative tocountercurrent solvent extraction,ion exchange is now used only to obtain the highest purities of lanthanides (typically greater than 99.99%).[citation needed]

Medicine

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Sodium calcium edetate,an EDTA derivative, is used to bind metal ions in the practice ofchelation therapy,such as for treatingmercuryandlead poisoning.[9]It is used in a similar manner to remove excessironfrom the body. This therapy is used to treat the complication of repeatedblood transfusions,as would be applied to treatthalassaemia.

Dentistry

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Dentistsandendodontistsuse EDTA solutions to remove inorganic debris (smear layer) and lubricate theroot canalsin endodontics. This procedure helps prepare root canals forobturation.Furthermore, EDTA solutions with the addition of asurfactantloosen upcalcificationsinside a root canal and allow instrumentation (canal shaping) and facilitate apical advancement of a file in a tight or calcified root canal towards the apex.

Eyedrops

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It serves as apreservative(usually to enhance the action of another preservative such asbenzalkonium chlorideorthiomersal) in ocular preparations andeyedrops.

Analysis

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Inmedical diagnosisand organ function tests (here,kidney functiontest), thechromium(III)complex [Cr(EDTA)]−(as radioactivechromium-51(51Cr)) is administeredintravenouslyand its filtration into theurineis monitored. This method is useful for evaluatingglomerular filtration rate(GFR) innuclear medicine.[10]

EDTA is used extensively in the analysis of blood. It is ananticoagulantfor blood samples forCBC/FBCs,where the EDTA chelates the calcium present in the blood specimen, arresting the coagulation process and preserving blood cell morphology.[11]Tubes containing EDTA are marked withlavender(purple) or pink tops.[12]EDTA is also in tan top tubes for lead testing and can be used in royal blue top tubes for trace metal testing.[12]

EDTA is a slime dispersant, and has been found to be highly effective in reducing bacterial growth during implantation ofintraocular lenses(IOLs).[13]

Alternative medicine

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Somealternative practitionersbelieve EDTA acts as anantioxidant,preventingfree radicalsfrom injuringblood vesselwalls, therefore reducingatherosclerosis.[14]These ideas are unsupported by scientific studies, and seem to contradict some currently accepted principles.[15]TheU.S. FDAhas not approved it for the treatment of atherosclerosis.[16]

Cosmetics

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Inshampoos,cleaners, and other personal care products, EDTA salts are used as a sequestering agent to improve their stability in air.[17]

Laboratory applications

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In the laboratory, EDTA is widely used for scavenging metal ions: Inbiochemistryandmolecular biology,ion depletion is commonly used to deactivatemetal-dependent enzymes,either as an assay for their reactivity or to suppress damage toDNA,proteins,andpolysaccharides.[18]EDTA also acts as a selectiveinhibitoragainst dNTP hydrolyzing enzymes (Taq polymerase,dUTPase,MutT),[19]liverarginase[20]andhorseradish peroxidase[21]independently of metal ionchelation.These findings urge the rethinking of the utilisation of EDTA as a biochemically inactive metal ion scavenger in enzymatic experiments. In analytical chemistry, EDTA is used incomplexometric titrationsand analysis ofwater hardnessor as amasking agentto sequester metal ions that would interfere with the analyses.

EDTA finds many specialised uses in the biomedical labs, such as inveterinaryophthalmologyas ananticollagenaseto prevent the worsening ofcorneal ulcers in animals.Intissue culture,EDTA is used as a chelating agent that binds tocalciumand prevents joining ofcadherinsbetween cells, preventing clumping of cells grown in liquid suspension, or detaching adherent cells forpassaging.Inhistopathology,EDTA can be used as a decalcifying agent making it possible to cut sections using amicrotomeonce the tissue sample is demineralised.

EDTA is also known to inhibit a range ofmetallopeptidases,the method of inhibition occurs via thechelationof the metal ion required for catalytic activity.[22]EDTA can also be used to test forbioavailabilityof heavy metals insediments.However, it mayinfluencethe bioavailability of metals in solution, which may pose concerns regarding its effects in the environment, especially given its widespread uses and applications.

EDTA is also used to remove crud (corroded metals) from fuel rods in nuclear reactors.[23]

Side effects

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EDTA exhibits low acute toxicity withLD50(rat) of 2.0 g/kg to 2.2 g/kg.[4]It has been found to be bothcytotoxicand weaklygenotoxicin laboratory animals. Oral exposures have been noted to cause reproductive and developmental effects.[17]The same study[17]also found that both dermal exposure to EDTA in most cosmetic formulations and inhalation exposure to EDTA inaerosolisedcosmetic formulations would produce exposure levels below those seen to be toxic in oral dosing studies.

Synthesis

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The compound was first described in 1935 byFerdinand Münz,[24]who prepared the compound fromethylenediamineandchloroacetic acid.[25]Today, EDTA is mainly synthesised fromethylenediamine(1,2-diaminoethane),formaldehyde,andsodium cyanide.[26]This route yields the tetrasodium EDTA, which is converted in a subsequent step into the acid forms:

H2NCH2CH2NH2+ 4CH2O+ 4NaCN+ 4 H2O → (NaO2CCH2)2NCH2CH2N(CH2CO2Na)2+ 4NH3
(NaO2CCH2)2NCH2CH2N(CH2CO2Na)2+ 4HCl→ (HO2CCH2)2NCH2CH2N(CH2CO2H)2+ 4NaCl

This process is used to produce about 80,000 tonnes of EDTA each year. Impurities cogenerated by this route includeglycineandnitrilotriacetic acid;they arise from reactions of theammoniacoproduct.[4]

Nomenclature

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To describe EDTA and its variousprotonated forms,chemists distinguish between EDTA4−,theconjugate basethat is theligand,and H4EDTA, theprecursorto that ligand. At very low pH (very acidic conditions) the fully protonated H6EDTA2+form predominates, whereas at very high pH or very basic condition, the fully deprotonated EDTA4−form is prevalent. In this article, the term EDTA is used to mean H4−xEDTAx−,whereas in its complexes EDTA4−stands for the tetraanion ligand.

Coordination chemistry principles

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Metal–EDTAchelateas found in Co(III) complexes
Structure of [Fe(EDTA)(H2O)]−,showing that the EDTA4−ligand does not fully encapsulateFe(III),which is seven-coordinate[27]

Incoordination chemistry,EDTA4−is a member of theaminopolycarboxylic acidfamily of ligands. EDTA4−usually binds to a metal cation through its two amines and four carboxylates, i.e., it is ahexadentate( "six-toothed" )chelating agent.Many of the resultingcoordination compoundsadoptoctahedral geometry.Although of little consequence for its applications, these octahedral complexes arechiral.Thecobalt(III)anion [Co(EDTA)]−has been resolved intoenantiomers.[28]Many complexes of EDTA4−adopt more complex structures due to either the formation of an additional bond to water,i.e.seven-coordinate complexes, or the displacement of one carboxylate arm by water. Theiron(III)complexof EDTA is seven-coordinate.[29]Early work on the development of EDTA was undertaken byGerold Schwarzenbachin the 1940s.[30]EDTA forms especially strong complexes withMn(II),Cu(II),Fe(III),Pb(II)and Co(III).[31][page needed]

Several features of EDTA's complexes are relevant to its applications. First, because of its highdenticity,this ligand has a high affinity for metal cations:

[Fe(H2O)6]3++ H4EDTA ⇌ [Fe(EDTA)]−+ 6 H2O + 4 H+Keq= 1025.1

Written in this way, theequilibrium quotientshows that metal ions compete with protons for binding to EDTA. Because metal ions are extensively enveloped by EDTA, theircatalytic propertiesare often suppressed. Finally, since complexes of EDTA4−areanionic,they tend to be highly soluble in water. For this reason, EDTA is able to dissolve deposits ofmetal oxidesandcarbonates.

ThepKavaluesof free EDTA are 0, 1.5, 2, 2.66 (deprotonationof the fourcarboxyl groups) and 6.16, 10.24 (deprotonation of the twoamino groups).[32]

Environmental concerns

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Abiotic degradation

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EDTA is in such widespread use that questions have been raised whether it is apersistent organic pollutant.While EDTA serves many positive functions in different industrial, pharmaceutical and other avenues, the longevity of EDTA can pose serious issues in the environment. The degradation of EDTA is slow. It mainly occursabioticallyin the presence of sunlight.[33]

The most important process for the elimination of EDTA from surface waters is directphotolysisat wavelengths below 400 nm.[34]Depending on the light conditions, the photolysishalf-livesof iron(III) EDTA in surface waters can range as low as 11.3 minutes up to more than 100 hours.[35]Degradation of FeEDTA, but not EDTA itself, produces iron complexes of the triacetate (ED3A), diacetate (EDDA), and monoacetate (EDMA) – 92% of EDDA and EDMA biodegrades in 20 hours while ED3A displays significantly higher resistance. Many environmentally-abundant EDTA species (such asMg2+andCa2+) are more persistent.

Biodegradation

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In manyindustrial wastewater treatmentplants, EDTA elimination can be achieved at about 80% usingmicroorganisms.[36]Resulting byproducts are ED3A andiminodiacetic acid(IDA) – suggesting that both the backbone and acetyl groups were attacked. Some microorganisms have even been discovered to form nitrates out of EDTA, but they function optimally at moderately alkaline conditions of pH 9.0–9.5.[37]

Several bacterial strains isolated from sewage treatment plants efficiently degrade EDTA. Specific strains includeAgrobacterium radiobacterATCC 55002[38]and the sub-branches ofPseudomonadotalike BNC1, BNC2,[39]and strain DSM 9103.[40]The three strains share similar properties ofaerobic respirationand are classified asgram-negative bacteria.Unlike photolysis, the chelated species is not exclusive to iron(III) in order to be degraded. Rather, each strain uniquely consumes varying metal–EDTA complexes through several enzymatic pathways. Agrobacterium radiobacter only degrades Fe(III) EDTA[39]while BNC1 and DSM 9103 are not capable of degrading iron(III) EDTA and are more suited forcalcium,barium,magnesiumandmanganese(II)complexes.[41]EDTA complexes require dissociation before degradation.

Alternatives to EDTA

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Interest in environmental safety has raised concerns about biodegradability ofaminopolycarboxylatessuch as EDTA. These concerns incentivize the investigation of alternative aminopolycarboxylates.[33]Candidate chelating agents includenitrilotriacetic acid(NTA), iminodisuccinic acid (IDS),polyaspartic acid,S,S-ethylenediamine-N,N′-disuccinic acid (EDDS),methylglycinediacetic acid (MGDA), andL-Glutamic acidN,N-diacetic acid, tetrasodium salt (GLDA).[42]

Iminodisuccinic acid (IDS)

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Commercially used since 1998,iminodisuccinic acid(IDS) biodegrades by about 80% after only 7 days. IDS binds to calcium exceptionally well and forms stable compounds with other heavy metal ions. In addition to having a lower toxicity after chelation, IDS is degraded byAgrobacterium tumefaciens(BY6), which can be harvested on a large scale. The enzymes involved,IDS epimeraseand C−Nlyase,do not require anycofactors.[43]

Polyaspartic acid

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Polyaspartic acid,like IDS, binds to calcium and other heavy metal ions. It has many practical applications including corrosion inhibitors, wastewater additives, and agricultural polymers. A Polyaspartic acid-basedlaundry detergentwas the first laundry detergent in the world to receive theEU flower ecolabel.[44]Calcium binding ability of polyaspartic acid has been exploited for targeting of drug-loaded nanocarriers to bone.[45]Preparation ofhydrogelsbased on polyaspartic acid, in a variety of physical forms ranging fromfibertoparticle,can potentially enable facile separation of the chelated ions from a solution.[46]Therefore, despite being weaker than EDTA, polyaspartic acid can still be regarded as a viable alternative due to these features as well asbiocompatibility,andbiodegradability.[47]

S,S-Ethylenediamine-N,N′-disuccinic acid (EDDS)

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Astructural isomerof EDTA,ethylenediamine-N,N′-disuccinic acid(EDDS) is readily biodegradable at high rate in itsS,Sform.[48]

Methylglycinediacetic acid (MGDA)

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Trisodium dicarboxymethyl alaninate,also known as methylglycinediacetic acid (MGDA), has a high rate of biodegradation at over 68%, but unlike many other chelating agents can degrade without the assistance of adapted bacteria. Additionally, unlike EDDS or IDS, MGDA can withstand higher temperatures while maintaining a high stability as well as the entire pH range.[citation needed]MGDA has been shown to be an effective chelating agent, with a capacity for mobilization comparable with that ofnitrilotriacetic acid(NTA), with application to water for industrial use and for the removal ofcalcium oxalatefrom urine from patients withkidney stones.[49]

Methods of detection and analysis

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The most sensitive method of detecting and measuring EDTA in biological samples is selected reaction monitoringcapillary electrophoresismass spectrometry(SRM-CE/MS), which has adetection limitof 7.3 ng/mL in human plasma and aquantitation limitof 15 ng/mL.[50]This method works with sample volumes as small as 7–8 nL.[50]

EDTA has also been measured in non-alcoholic beverages usinghigh performance liquid chromatography(HPLC) at a level of 2.0 μg/mL.[51][52]

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In the movieBlade(1998), EDTA is used as a weapon to kill vampires, exploding when in contact with vampire blood.[53]

References

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  3. ^Substance Name: Sodium calcium edetate.NIH.gov
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