EDTA
Chemical name	EDTA
Other names	EDTA H4EDTA Diaminoethanetetraacetic acid Edetic acid Edetate Ethylenedinitrilotetraacetic acid Versene Ethylene diamine tetracetic acid
Chemical formula	C10H16N2O8
Molecular mass	292.25 g/mol
CAS number	[60-00-4]
Density	0.86 g/cm³
Melting point	237-245 °C (dec.)
SMILES	OC(CN(CC(O)=O)C- CN(CC(O)=O)CC(O)=O)=O Image File history File links Ethylenediaminetetraacetic. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article does not cite its references or sources. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ...
Hazards
MSDS	External MSDS
Main hazards	irritant
NFPA 704	0 1 0
R/S statement	R: 36 S: 26
RTECS number	AH4025000
Disclaimer and references

EDTA is a widely-used acronym for the chemical compound ethylenediamine tetraacetic 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. EDTA binds to metals via four carboxylate and two amine groups. EDTA forms specially strong complexes with Mn(II), Cu(II), Fe(III), and Co(III).^[1] An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to 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. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Chelation (from Greek, claw like) describes the reversible binding of an organic ligand, the chelator or chelating agent, to a metal ion, forming a metal complex, the chelate. ... This article does not cite its references or sources. ... Phenylalanine is one of the standard amino acids. ... Hot metal work from a blacksmith In chemistry, a metal (Greek: Metallon) is an element that readily loses electrons to form positive ions (cations) and has metallic bonds between metal atoms. ... An electrostatic potential map of the nitrate ion (NO3−). Areas coloured red are lower in energy than areas colored yellow An ion is an atom or group of atoms which have lost or gained one or more electrons, making them negatively or positively charged. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ...

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, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a...

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. complex In chemistry, a complex is a structure composed of a central metal atom or ion, generally a cation, surrounded by a number of negatively charged ions or neutral molecules possessing lone pairs. ... NTA is the chemical compound nitrilotriacetic acid. ... Phenylalanine is one of the standard amino acids. ... For the plant, see Glycine (plant). ...

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.^[2] Synthesis of copper(II)-tetraphenylporphine, a metal complex, from tetraphenylporphine and copper(II) acetate monohydrate. ... The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...

Metal-EDTA chelate

Image File history File links Metal-EDTA.png Summary Description: Chemical structure of EDTA chelate Author, date of creation: selfmade by Shaddack, 20 October 2005 Source: self-made Copyright: Public Domain (PD) Comments: b/w PNG; ChemWindow Licensing File links The following pages link to this file: Chelation EDTA ... Image File history File links Metal-EDTA.png Summary Description: Chemical structure of EDTA chelate Author, date of creation: selfmade by Shaddack, 20 October 2005 Source: self-made Copyright: Public Domain (PD) Comments: b/w PNG; ChemWindow Licensing File links The following pages link to this file: Chelation EDTA ... Chelation (from Greek, claw like) describes the reversible binding of an organic ligand, the chelator or chelating agent, to a metal ion, forming a metal complex, the chelate. ...

Uses

In 1999, the annual consumption of EDTA was equivalent to about 35,000 tons in Europe and 50,000 tons in the US.^{[citation needed]} 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 of EDTA are: A heavy metal is any of a number of higher atomic weight elements, which has the properties of a metallic substance at room temperature. ... Laundry detergents are just one of many possible uses for detergents Detergent is a compound, or a mixture of compounds, intended to assist cleaning. ... Photography [fәtɑgrәfi:],[foʊtɑgrәfi:] is the process of recording pictures by means of capturing light on a light-sensitive medium, such as a film or sensor. ... Pulp and Paper is the name of the largest United States-based trade magazine for the pulp and paper industry. ... Sunday textile market on the sidewalks of Karachi, Pakistan. ... Agrichemical (or agrochemical) is a generic term for the various synthetic chemical products manufactured and sold for use in agriculture. ... NASA researcher checking hydroponic onions with Bibb lettuce to his left and radishes to the right Hydroponics or hydroculture is crop production with mineral nutrient solutions instead of soil containing silt and clay. ...

• Food: added as preservative to prevent catalytic oxidation by metal ions or stabilizer and for iron fortification.^{[citation needed]}
• Personal care: added to cosmetics to improve product stability.^{[citation needed]}
• Oil production: added into the borehole to inhibit mineral precipitation.^{[citation needed]}
• Dairy and beverage industry: cleaning of bottles from milk stains.^{[citation needed]}
• Flue gas cleaning: removal of NO_x.
• Dentistry as a root canal irrigant to remove organic and inorganic debris (smear layer).^{[citation needed]}
• Soft drinks containing ascorbic acid and sodium benzoate, to mitigate formation of benzene (a carcinogen).^{[citation needed]}
• Recycling: recovery of used lead acid batteries.

Medicine: A preservative is a natural or synthetic chemical that is added to products such as foods, pharmaceuticals, paints, biological samples, etc. ... For other uses, see Cosmetic. ... Natural olive oil Synthetic motor oil An oil is any substance that is in a viscous liquid state (oily) at ambient temperatures or slightly warmer, and is both hydrophobic (immiscible with water, literally water fearing) and lipophilic (miscible with other oils, literally fat loving). This general definition includes compound classes... The 3 letter word/formula nox can mean: Nyx, a goddess of Night (nox is Latin for night). ... A Dentist and Dental Assistant perform surgery on a patient. ... This article or section does not cite any references or sources. ... A soft drink is a drink that contains no alcohol. ... This article deals with the molecular aspects of ascorbic acid. ... Sodium benzoate (E211), also called benzoate of soda, has chemical formula C6H5COONa. ... Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... This article needs additional references or sources to facilitate its verification. ... To meet Wikipedias quality standards, this article or section may require cleanup. ...

• EDTA is used in chelation therapy (brand name Endrate®, marketed by Hospira;generic product is also on the market) for acute hypercalcemia and mercury poisoning and has been used for lead poisoning.^{[citation needed]}.
• Combined whith chromium, EDTA is used to evuate kidney function. It is administered intravenously and it's filtration into the urine is montored. This method is considered the gold standard for evaluating glomerular filtration rate as Cr-EDTA's sole way out of the body is via glomerular filtration as it is not secreted or metaloized in any other way.
• Used as anticoagulant for blood samples

In laboratory science, EDTA is also used for: Chelation therapy is a process involving the use of chelating agents to remove heavy metals from the body. ... Hospira, Inc. ... A generic drug (pl. ... Hypercalcaemia is an elevated calcium level in the blood. ... It has been suggested that this article or section be merged with Mercury_toxicity. ... Lead poisoning is a medical condition, also known as saturnism, plumbism or painters colic, caused by increased blood lead levels. ... General Name, Symbol, Number chromium, Cr, 24 Chemical series transition metals Group, Period, Block 6, 4, d Appearance silvery metallic Standard atomic weight 51. ... Renal physiology is the study of the physiology of the kidneys. ... In medicine, a gold standard test is the diagnostic test that is regarded as definitive in determining whether an individual has a disease process. ... Glomerular filtration rate (GFR) is the volume of fluid filtered from the renal glomerular capillaries into Bowmans capsule per unit time. ... An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ...

• 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 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 a electroless nickel plating bath.

Biochemistry is the study of the chemical processes and transformations in living organisms. ... Molecular biology is the study of biology at a molecular level. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... Acids and bases: Acid-base reaction theories pH Self-ionization of water Buffer solutions Systematic naming Electrochemistry Acid-base extraction Acids: Strong acids Weak acids Superacids Lewis acids Mineral acids Organic acids Bases: Strong bases Weak bases Superbases Lewis bases Organic bases edit Buffer solutions are solutions which resist change... Hard water is water that has a high mineral content. ... The introduction to this article provides insufficient context for those unfamiliar with the subject matter. ... An anticoagulant is a substance that prevents coagulation; that is, it stops blood from clotting. ...

Environmental behavior

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. 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. Image File history File links Download high-resolution version (1100x1000, 273 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): EDTA ... Image File history File links Download high-resolution version (1100x1000, 273 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): EDTA ... Look up anthropogenic in Wiktionary, the free dictionary. ...

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. Sewage treatment is the process that removes the majority of the contaminants from waste-water or sewage and produces both a liquid effluent suitable for disposal to the natural environment and a sludge. ... The correct title of this article is . ... A cluster of Escherichia coli bacteria magnified 10,000 times. ...

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. Elevated concentrations of chelating agents enhance the transport of metals (e.g. Zn, Cd, Ni, Cr, Cu, Pb, and Fe) in soils, and enhance the undesired transport of radioactive metals away from disposal sites. 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. Photomontage of plankton organisms Plankton are any drifting organism that inhabits the water column of oceans, seas, and bodies of fresh water. ... A seaweed (Laurencia) up close: the branches are multicellular and only about 1 mm thick. ... Look up acute in Wiktionary, the free dictionary. ... Mitochondria structure : 1) Inner membrane 2) Outer membrane 3) Crista 4) Matrix The outer membrane refers to the outside membranes of Gram-negative bacteria, the chloroplast, or the mitochondria. ... // The cell membrane (also called the plasma membrane or plasmalemma) is a semipermeable lipid bilayer common to all living cells. ...

Trivia

• 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).
• "Ethylenediaminetetraacetates" is the longest hypothetically legal Scrabble word (hypothetical because it exceeds 15 letters, the width of a Scrabble board) in North American play.
• EDTA was used in the movie Blade as a weapon against vampires. In the movie, when mixed with vampire blood, it causes an unstable reaction to occur, the result of which is an explosion. When it is used on vampires, they explode.

The O.J. Simpson murder case was a highly publicized U.S. criminal trial in which former football star and actor O.J. Simpson was charged with the murder of one of his ex-wives and her friend. ... McDonalds Corporation (NYSE: MCD) is the worlds largest chain of fast-food restaurants, primarily selling hamburgers, chicken, french fries, milkshakes and soft drinks. ... The verb to scrabble also means to scratch, scramble or scrape about: see Wiktionary:scrabble. ... Blade is a 1998 film starring Wesley Snipes and Stephen Dorff, loosely based on the the Blade comics series. ...

See also

• EGTA
• NTA
• Phosphonate
• DTPA

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 affinity for calcium than for magnesium ions. ... NTA is the chemical compound nitrilotriacetic acid. ... Phosphonates or Phosphonic acids are organic compounds containing one or more C-PO(OH)2 groups. ... Diethylene triamine pentaacetic acid is an elongated version of EDTA. Categories: | | ...

References

1. ^ Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
2. ^ Kirchner, S. Barium (Ethylenediaminetetracetato) Cobalt(III) 4-Hydrate" Inorganic Syntheses, McGraw-Hill: New York, 1957; Vol. 5, pages 186-188.

External links

• pH-Spectrum of EDTA complexes
• EDTA: Molecule of the Month
• http://www.chem.utk.edu/~chem319/Experiments/Exp6.pdf
• Links to external chemical sources