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For other uses, see EDTA (disambiguation).
EDTA
Ball and stick model of the EDTA molecule, in the zwitterionic form found in the solid state
IUPAC name2-[2-(Bis(carboxymethyl)amino)ethyl-(carboxymethyl)amino]acetic acid
Other namesEDTA, H4EDTA, Diaminoethanetetraacetic acid, Edetic acid, Edetate, Ethylenedinitrilotetraacetic acid, Versene, Ethylene diamine tetraacetic acid
Identifiers
CAS number[60-00-4]
RTECS numberAH4025000
SMILESOC(CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O)=O
Properties
Molecular formulaC10H16N2O8
Density0. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 86 g/cm³
Melting point

237-245 °C (dec. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. )

Hazards
MSDSExternal MSDS
Main hazardsirritant
NFPA 704
0
1
0
 
R-phrasesR36
S-phrasesS26
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

EDTA is a widely-used abbreviation for the chemical compound ethylene diamine tetraacetic acid (and many other names, see table). A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. EDTA refers to the chelating agent with the formula (HO2CCH2)2NCH2CH2N(CH2CO2H)2. Chelation is the binding or complexation of a bi- or multidentate Ligand. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes This amino acid is widely used to sequester di- and trivalent metal ions. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this The M acro E xpansion T emplate A ttribute L anguage complements TAL, providing macros which allow the reuse of code across An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge EDTA binds to metals via four carboxylate and two amine groups. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. EDTA forms especially strong complexes with Mn(II), Cu(II), Fe(III), Pb (II) and Co(III). [1]

Contents

Synthesis

EDTA is mostly synthesised from 1,2-diaminoethane (ethylenediamine), formaldehyde (methanal), water and sodium cyanide. Ethylenediamine (abbreviated as en when a Ligand) is the Organic compound with the formula C2H4(NH22 [2] 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 1940's. Gerold Karl Schwarzenbach ( March 15, 1904 - May 20, 1978) was a Swiss Chemist. [3] DOSE WORK WELL

Isomer

EDTA exists in different standard form 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. In chemistry protonation is the addition of a proton ( H[[Cation +]] to an Atom, Molecule, or Ion. In Chemistry, a ligand is either an Atom, Ion, or Molecule (see also Functional group) that bonds to a central metal generally

Synonyms

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.

Coordination chemistry principles

Metal-EDTA chelate
Metal-EDTA chelate

In coordination chemistry, H4EDTA is a member of the aminocarboxylate family of ligands that includes imidodiacetic acid ("H2IDA") and nitrilotriacetic acid ("H3NTA"). Chelation is the binding or complexation of a bi- or multidentate Ligand. The term complex in Chemistry is usually used to describe molecules or ensembles formed by the combination of Ligands and metal Ions. Nitrilotriacetic acid (NTA C6H9NO6 is a chemical compound used as a Chelating agent which forms Coordination compounds with metal 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. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Glycine (abbreviated as Gly or G) is the Organic compound with the formula NH2CH2COOH

H4EDTA forms highly stable coordination compounds that are soluble in water. The term complex in Chemistry is usually used to describe molecules or ensembles formed by the combination of Ligands and metal Ions. 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. The term chiral (pronounced /ˈkaɪɹ(əl̩/ is used to describe an object that is non- superimposable on its mirror image In Chemistry, an enantiomer ( from the Greek ἐνάντιος opposite and μέρος part or portion is one of two Stereoisomers that are nonsuperimposable [4]

Uses

In 1999, the annual consumption of EDTA was equivalent to about 35,000 tons in Europe and 50,000 tons in the US. The most important uses are:

More specialised uses of EDTA are:

Medicine:

In laboratory science, EDTA is also used for:

Toxicity

EDTA has been found to be both cytotoxic and weakly genotoxic in laboratory animals. Cytotoxicity is the quality of being toxic to cells Examples of toxic agents are a Chemical substance, an Immune cell or some types of Venom Genotoxicity describes a deleterious action on a cell genetic material affecting its integrity Oral exposures have been noted to cause reproductive and developmental effects. [6] The same study by Lanigan[6] 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

EDTA coordinating a Cu2+ ion
EDTA coordinating a Cu2+ ion

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. Anthropogenic effects processes objects or materials are those that are derived from Human activities as opposed to those occurring in Natural environments without River concentrations in Europe are reported as 10-100 μg/L, and lake concentrations are in the 1-10 μg/L range. In the Metric system, a microgram is 1/1000000 of a Gram (1 × 10-6 or 1/1000 of a milligram is one of the smallest units of weight/mass commonly used The litre or liter (see spelling differences) is a unit of Volume. 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. Sewage treatment, or domestic wastewater treatment, is the process of removing Contaminants from Wastewater, both Runoff ( Effluents However, an adjustment of pH and sludge residence time can result in almost complete mineralization of EDTA. pH is the measure of the acidity or alkalinity of a Solution. 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. A microorganism (also spelled micro organism or micro-organism and also called a microbe) is an Organism that is Microscopic (usually

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. Plankton consist of any drifting Organisms ( Animals Plants Archaea, or Bacteria) that inhabit the Pelagic zone of Algae ( sing. alga are a large and diverse group of simple typically Autotrophic organisms ranging from Unicellular to Multicellular forms Chelating agents are nontoxic to many forms of life on acute exposure; the effects of longer-term low-level exposure are unknown. In Medicine, an acute disease is a disease with either or both of a rapid onset a short course (as opposed to a chronic course EDTA at elevated concentrations is toxic to bacteria due to chelation of metals in the outer membrane. The outer membrane refers to the outside membranes of Gram-negative bacteria, the Chloroplast, or the Mitochondria. EDTA ingestion at high concentrations by mammals changes excretion of metals and can affect cell membrane permeability. The cell membrane (also called the plasma membrane, plasmalemma, or "phospholipid bilayer" is a Selectively permeable Lipid bilayer

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. Capillary electrophoresis ( CE) also known as capillary zone electrophoresis (CZE can be used to separate ionic species by their charge and frictional forces Liquid chromatography-mass spectrometry ( LC-MS) is an Analytical chemistry technique that combines the physical separation capabilities of liquid chromatography In Analytical chemistry, the detection limit, lower limit of detection, or LOD (limit of detection is the lowest quantity of a substance that can be distinguished 3 ng/mL in human plasma and a quantitation limit of 15 ng/mL. In Analytical chemistry, the detection limit, lower limit of detection, or LOD (limit of detection is the lowest quantity of a substance that can be distinguished [9] This method works with sample volumes as small as ~7-8 nL. [9]

EDTA has also been measured in non-alcoholic beverages using high performance liquid chromatography (HPLC) which has a detection limit of 0. High-performance liquid chromatography (or High pressure liquid chromatography, HPLC) is a form of Column chromatography used frequently in Biochemistry In Analytical chemistry, the detection limit, lower limit of detection, or LOD (limit of detection is the lowest quantity of a substance that can be distinguished 6 μg/mL and a quantitation limit of 2. In Analytical chemistry, the detection limit, lower limit of detection, or LOD (limit of detection is the lowest quantity of a substance that can be distinguished 0 μg/mL. [10][11]

Forensics

See also

References

  1. ^ Holleman, A. 23-Dimercapto-1-propanesulfonic acid (abbreviated DMPS) and its sodium salt (known as Unithiol) are Chelating agents that form complexes with various Dimercaptosuccinic acid, or DMSA is the Chemical compound with the formula HO2CCH(SHCH(SHCO2H Diethylene triamine pentaacetic acid (DTPA is an Organic compound consisting of a Diethylenetriamine backbone modified with five carboxymethyl groups EGTA is the Chemical compound ethylene glycol tetraacetic acid, a Chelating agent that is related to the better known EDTA, but with a much higher Lead poisoning (also known as saturnism, plumbism, or painter's colic) is a medical condition caused by increased levels of the metal Lead in Mercury poisoning (also known as mercurialism, hydrargyria, Hunter-Russell syndrome, or acrodynia when affecting children is a Disease Nitrilotriacetic acid (NTA C6H9NO6 is a chemical compound used as a Chelating agent which forms Coordination compounds with metal Phosphonates or Phosphonic acids are organic compounds containing one or more C-PO(OH2 or C-PO(OR2 (with R= Alkyl, Aryl) groups F. ; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. ISBN 0-12-352651-5.  
  2. ^ Synthesis of EDTA
  3. ^ Edta - Motm
  4. ^ Kirchner, S. Barium (Ethylenediaminetetracetato) Cobalt(III) 4-Hydrate" Inorganic Syntheses, McGraw-Hill: New York, 1957; Vol. 5, pages 186-188.
  5. ^ Furia T (1964). "EDTA in Foods — A technical review". Food Technology 18 (12): 1874-1882.  
  6. ^ a b c Lanigan RS and Yamarik TA (2002). "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". Int J Toxicol. 21 Suppl 2: 95-142.  
  7. ^ Ruth DeBusk et al. (2002). Ethylenediaminetetraacetic acid (EDTA). Retrieved on 2007-07-25. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 285 - Diocletian appoints Maximian as Caesar, co-ruler
  8. ^ |http://www.clinicaltrials.gov/ct/show/NCT00044213?order=2
  9. ^ a b Robin L. Sheppard, and Jack Henion (1997). "Determining EDTA in Blood". Analytical Chemistry 69: 477A-480A.  
  10. ^ S. Loyaux-Lawniczak, J. Douch, and P. Behra (1999). "Optimisation of the analytical detection of EDTA by HPLC in natural waters". Fresenius' J. Anal. Chem. 364 (8): 727-731. doi:10.1007/s002160051422. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. ISSN 0937-0633. An International Standard Serial Number ( ISSN) is a unique eight-digit number used to identify a print or electronic Periodical publication.  
  11. ^ Carolina E. Cagnassoa, Laura B. López, Viviana G. Rodríguez and Mirta E. Valencia (May 2006). "Development and validation of a method for the determination of EDTA in non-alcoholic drinks by HPLC". Journal of Food Composition and Analysis 20 (3-4): 248. doi:10.1016/j.jfca.2006.05.008. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  

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