DISODIUM ETHYLENEDIAMINETETRAACETATE

Disodium ethylenediaminetetraacetate is widely used in industry.
Disodium ethylenediaminetetraacetate is used in pharmaceutical manufacturing and as a food additive.
Disodium ethylenediaminetetraacetate is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble.

CAS Number: 139‑33‑3 (anhydrous), 6381‑92‑6 (dihydrate) 
EC Number: 205‑358‑3 
MDL Number: MFCD00070672
IUPAC Name: Disodium N,N′-(ethane-1,2-diyl)bis[N-(carboxymethyl)glycinate] (ethylenediaminetetraacetate disodium salt) 
Molecular Formula / Mass: C₁₀H₁₄N₂Na₂O₈ · xH₂O; 
Molar mass: ~336.2 g/mol (anhydrous)

SYNONYMS:
Disodium EDTA, Ethylenediamine‑tetraacetic acid disodium salt, Edetate disodium, Edetate disodium dihydrate, Disodium edetate, EDTA‑2Na, Disodium EDTA, Ethylenediamine‑tetraacetic acid disodium salt, Disodium edetate, Edetate disodium, EDTA‑2Na, Disodium edetate dihydrate, Ethylenedinitrilo tetraacetic acid disodium salt, N,N′-(Ethane-1,2-diyl)bis[N-(carboxymethyl)glycine], 2,2′,2′′,2′′′-(Ethane-1,2-diyldinitrilo)tetraacetic acid, EthyleneDiamineTetraAcetic acid, Diaminoethane-tetraacetic acid, Edetic acid (conjugate base edetate) (INN, USAN), Versene, 139-33-3, EDTA disodium salt, Edetate disodium anhydrous, Edta disodium, Ethylenediaminetetraacetic acid disodium salt, Titriplex III, Disodium EDTA, Disodium edta, anhydrous, Endrate disodium, Anhydrous disodium edetate, Disodium ethylenediaminetetraacetate, Edetate disodium, anhydrous, Edetic Acid, Disodium Salt, Glycine, N,N'-1,2-ethanediylbis[N-(carboxymethyl)-, disodium salt, Ethylenediaminetetraacetic acid, disodium salt, MFCD00070672, Disodium (ethylenedinitrilo)tetraacetate, 8NLQ36F6MM, EDTA-Na2, EDTA disodium salt (anhydrous), Ethylene diamine tetraacetic acid, disodium salt, Glycine, N,N'-1,2-ethanediylbis(N-(carboxymethyl)-, disodium salt, Endrate (TN), Disodium edathamil, disodium 2-({2-[(carboxylatomethyl)(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetate, Tetracemate disodium, Na2-EDTA, E.D.T.A. disodique [French], F 1 (VAN), ethylenediamine tetraacetic acid disodium salt, Dinatrium ethylendiamintetraacetat [Czech], Ethylenebis(iminodiacetic acid) disodium salt, (Ethylenedinitrilo)-tetraacetic acid disodium salt, Na2EDTA, 0.5M Sodium EDTA, Disodium edetate (TN), Na2.EDTA, CHEMBL1749, SCHEMBL49459, DTXSID9027073, EDETATE DISODIUM [WHO-DD], disodium ethylenediamine-tetraacetate, AKOS016370696, DB14600, SB40706, 69772-70-9, E386, EDTA DISODIUM SALT ANHYDROUS [MI], ethylenediaminetetracetic acid disodium salt, DB-042467, NS00078150, EN300-35828, ethylenediaminetetra-acetic acid disodium salt, D03945, P17519, Q4532977, Ethylenediaminetetraacetic acid disodium salt, (2% solution), disodium 2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetate, Glycine, N,N'-1,2-ethanediylbis(N-(carboxymethyl)-, sodium salt (1:2), (Ethylenedinitrilo)tetraacetic acid disodium salt, EDTA disodium salt, EDTA-Na2, 2-[2-(Carboxylatomethyl-(carboxymethyl)amino)ethyl-(carboxymethyl)amino]acetate disodium, disodium;2-[2-[carboxylatomethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate, DISODIUM 2-({2-[(CARBOXYLATOMETHYL)(CARBOXYMETHYL)AMINO]ETHYL(CARBOXYMETHYL)AMINO)ACETATE, Disodium dihydrogen ethylenediaminetetraacetate, Ethylenediaminetetraacetic acid disodium salt, Disodium ethylenediaminetetraacetate dihydrate, EDTA disodium salt, EDTA-Na2, Edathamil, Edetate disodium salt dihydrate, Sequestrene Na2, Ethylenediaminetetraacetic acid disodium salt dihydrate, Ethylenediaminetetraacetic Acid, 2Na, Disodium ethylenediaminetetraacetate dihydrate, EDTA disodium salt, EDTA-Na2, Edathamil, Edetate disodium salt dihydrate, Sequestrene Na2

Disodium ethylenediaminetetraacetate is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1982 and is indicated for eye disease and has 4 investigational indications.
Disodium ethylenediaminetetraacetate is a chelating agent that sequesters a variety of polyvalent cations such as CALCIUM.

Disodium ethylenediaminetetraacetate, also called EDTA acid, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2.
Disodium ethylenediaminetetraacetate was used in separation of the lanthanide metals by ion-exchange chromatography.
Perfected by F. H. Spedding et al. in 1954, the method relies on the steady increase in stability constant of the lanthanide Disodium ethylenediaminetetraacetate complexes with atomic number.

Using sulfonated polystyrene beads and Cu2+ as a retaining ion, Disodium ethylenediaminetetraacetate 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 to countercurrent solvent extraction, ion exchange is now used only to obtain the highest purities of lanthanides (typically greater than 99.99%).

Disodium ethylenediaminetetraacetate is a slime dispersant, and has been found to be highly effective in reducing bacterial growth during implantation of intraocular lenses (IOLs).
In coordination chemistry, Disodium ethylenediaminetetraacetate 4− is a member of the aminopolycarboxylic acid family of ligands.

Disodium ethylenediaminetetraacetate4− usually binds to a metal cation through its two amines and four carboxylates, i.e., it is a hexadentate ("six-toothed") chelating agent.
Many of the resulting coordination compounds adopt octahedral geometry.

Although of little consequence for its applications, these octahedral complexes are chiral.
The cobalt(III) anion [Co(EDTA)]− has been resolved into enantiomers.
Many complexes of Disodium ethylenediaminetetraacetate 4− 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.

The iron(III) complex of Disodium ethylenediaminetetraacetate is seven-coordinate.
Early work on the development of Disodium ethylenediaminetetraacetate was undertaken by Gerold Schwarzenbach in the 1940s.
Disodium ethylenediaminetetraacetate forms especially strong complexes with Mn(II), Cu(II), Fe(III), Pb(II) and Co(III).

Several features of Disodium ethylenediaminetetraacetate's complexes are relevant to its applications.
First, because of its high denticity, this ligand has a high affinity for metal cations:
[Fe(H2O)6]3+ + H4EDTA ⇌ [Fe(EDTA)]− + 6 H2O + 4 H+ Keq = 10^25.1

Written in this way, the equilibrium quotient shows that metal ions compete with protons for binding to Disodium ethylenediaminetetraacetate.
Because metal ions are extensively enveloped by Disodium ethylenediaminetetraacetate, their catalytic properties are often suppressed.
Finally, since complexes of Disodium ethylenediaminetetraacetate 4− are anionic, they tend to be highly soluble in water.

For this reason, Disodium ethylenediaminetetraacetate is able to dissolve deposits of metal oxides and carbonates.
The pKa values of free Disodium ethylenediaminetetraacetate are 0, 1.5, 2, 2.66 (deprotonation of the four carboxyl groups) and 6.16, 10.24 (deprotonation of the two amino groups).

Disodium ethylenediaminetetraacetate disodium salt, dihydrate is a chelating agent for metal ions in aqueous solution like Fe3+, Co2+, Fe2+, Mn2+, Ca2+, and Mg2+.
Disodium ethylenediaminetetraacetate is a chelating agent, used to sequester and decrease the reactivity of metal ions that may be present in a product.

Disodium ethylenediaminetetraacetate is a chelator of divalent cations.
Disodium ethylenediaminetetraacetate inhibits enzymes, such as metalloproteases, that require divalent cations for activity.

USES and APPLICATIONS of DISODIUM ETHYLENEDIAMINETETRAACETATE:
Food Additive & Preservative: Stabilizer in canned vegetables, dressings, beverages, soft drinks – prevents color discoloration and oxidative degradation.
Cosmetics & Personal Care: Disodium ethylenediaminetetraacetate is used in shampoos, lotions, creams to enhance foam and prevent metal-caused instability.

Pharmaceutical & Medical: Disodium ethylenediaminetetraacetate is used a chelation agent for treatment of lead or hypercalcemia, and in lab reagents; also anticoagulant in blood collection tubes.
Industrial & Laboratory Reagent: Disodium ethylenediaminetetraacetate sequesters hardness ions in detergents, textile processing, paper production, photographic solutions.

Disodium ethylenediaminetetraacetate is widely used in industry.
Disodium ethylenediaminetetraacetate also has applications in food preservation, medicine, cosmetics, water softening, in laboratories, and other fields.

This white, slightly water-soluble solid, Disodium ethylenediaminetetraacetate, is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH.
Disodium ethylenediaminetetraacetate is used in pharmaceutical manufacturing and as a food additive.

Disodium ethylenediaminetetraacetate is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble.
Disodium ethylenediaminetetraacetate is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.

Sodium calcium edetate, an Disodium ethylenediaminetetraacetate derivative, is used to bind metal ions in the practice of chelation therapy, such as for treating mercury and lead poisoning.
Disodium ethylenediaminetetraacetate is used in a similar manner to remove excess iron from the body.

This therapy is used to treat the complication of repeated blood transfusions, as would be applied to treat thalassaemia.
In medical diagnosis and organ function tests (here, kidney function test), the chromium(III) complex [Cr(EDTA)]− (as radioactive chromium-51 (51Cr)) is administered intravenously and its filtration into the urine is monitored.

This method is useful for evaluating glomerular filtration rate (GFR) in nuclear medicine.
Disodium ethylenediaminetetraacetate is used extensively in the analysis of blood.
It is an anticoagulant for blood samples for CBC/FBCs, where the Disodium ethylenediaminetetraacetate chelates the calcium present in the blood specimen, arresting the coagulation process and preserving blood cell morphology.

Tubes containing Disodium ethylenediaminetetraacetate are marked with lavender (purple) or pink tops.
Disodium ethylenediaminetetraacetate is also in tan top tubes for lead testing and can be used in royal blue top tubes for trace metal testing.
Dentists and endodontists use Disodium ethylenediaminetetraacetate solutions to remove inorganic debris (smear layer) and lubricate the root canals in endodontics.

This procedure helps prepare root canals for obturation.
Furthermore, Disodium ethylenediaminetetraacetate solutions with the addition of a surfactant loosen up calcifications inside 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.

Disodium ethylenediaminetetraacetate serves as a preservative (usually to enhance the action of another preservative such as benzalkonium chloride or thiomersal) in ocular preparations and eyedrops.
Some alternative practitioners believe Disodium ethylenediaminetetraacetate acts as an antioxidant, preventing free radicals from injuring blood vessel walls, therefore reducing atherosclerosis.

In shampoos, cleaners, and other personal care products, Disodium ethylenediaminetetraacetate salts are used as a sequestering agent to improve their stability in air.
The oxidising properties of [Fe(EDTA)]− are used in photography to solubilise silver particles.

Disodium ethylenediaminetetraacetate is also used to remove crud (corroded metals) from fuel rods in nuclear reactors.
Disodium ethylenediaminetetraacetate finds many specialised uses in the biomedical labs, such as in veterinary ophthalmology as an anticollagenase to prevent the worsening of corneal ulcers in animals.

In tissue culture, Disodium ethylenediaminetetraacetate is used as a chelating agent that binds to calcium and prevents joining of cadherins between cells, preventing clumping of cells grown in liquid suspension, or detaching adherent cells for passaging.
In histopathology, Disodium ethylenediaminetetraacetate can be used as a decalcifying agent making it possible to cut sections using a microtome once the tissue sample is demineralised.

Disodium ethylenediaminetetraacetate is also known to inhibit a range of metallopeptidases, the method of inhibition occurs via the chelation of the metal ion required for catalytic activity.
Disodium ethylenediaminetetraacetate can also be used to test for bioavailability of heavy metals in sediments.

-Industrial uses of Disodium ethylenediaminetetraacetate:
Disodium ethylenediaminetetraacetate is mainly used to sequester (bind or confine) metal ions in aqueous solution.
In the textile industry, Disodium ethylenediaminetetraacetate prevents metal ion impurities from modifying colours of dyed products.

In the pulp and paper industry, Disodium ethylenediaminetetraacetate inhibits the ability of metal ions, especially Mn2+, from catalysing the disproportionation of hydrogen peroxide, which is used in chlorine-free bleaching.

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

2 [Fe(Disodium ethylenediaminetetraacetate)]− + H2S → 2 [Fe(Disodium ethylenediaminetetraacetate)]2− + S + 2 H+
In this application, the iron(III) centre is reduced to its iron(II) derivative, which can then be reoxidised by air.
In a similar manner, nitrogen oxides are removed from gas streams using [Fe(Disodium ethylenediaminetetraacetate)]2−.

-Food uses of Disodium ethylenediaminetetraacetate:
In a similar manner, Disodium ethylenediaminetetraacetate is added to some food as a preservative or stabiliser to prevent catalytic oxidative decolouration, which is catalysed by metal ions.

-Water softener uses of Disodium ethylenediaminetetraacetate:
The reduction of water hardness in laundry applications and the dissolution of scale in boilers both rely on Disodium ethylenediaminetetraacetate and related complexants to bind Ca2+, Mg2+, as well as other metal ions.

Once bound to Disodium ethylenediaminetetraacetate, these metal complexes are less likely to form precipitates or to interfere with the action of the soaps and detergents.
For similar reasons, cleaning solutions often contain Disodium ethylenediaminetetraacetate.

In a similar manner Disodium ethylenediaminetetraacetate is used in the cement industry for the determination of free lime and free magnesia in cement and clinkers.

The solvation of Fe3+ ions at or below near neutral pH can be accomplished using Disodium ethylenediaminetetraacetate.
This property is useful in agriculture including hydroponics.

However, given the pH dependence of ligand formation, Disodium ethylenediaminetetraacetate is not helpful for improving iron solubility in above neutral soils.
Otherwise, at near-neutral pH and above, iron(III) forms insoluble salts, which are less bioavailable to susceptible plant species.

-Laboratory applications of Disodium ethylenediaminetetraacetate:
In the laboratory, Disodium ethylenediaminetetraacetate is widely used for scavenging metal ions:
In biochemistry and molecular biology, ion depletion is commonly used to deactivate metal-dependent enzymes, either as an assay for their reactivity or to suppress damage to DNA, proteins, and polysaccharides.

Disodium ethylenediaminetetraacetate also acts as a selective inhibitor against dNTP hydrolyzing enzymes (Taq polymerase, dUTPase, MutT), liver arginase and horseradish peroxidase independently of metal ion chelation.

These findings urge the rethinking of the utilisation of Disodium ethylenediaminetetraacetate as a biochemically inactive metal ion scavenger in enzymatic experiments.
In analytical chemistry, Disodium ethylenediaminetetraacetate is used in complexometric titrations and analysis of water hardness or as a masking agent to sequester metal ions that would interfere with the analyses.

RELATED COMPOUNDS OF DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Related alkanoic acids    
Daminozide
Octopine

-Related compounds    
Triethylenetetramine
Tetraacetylethylenediamine
PMDTA
Bis-tris propane

CHEMICAL CLASS AND MECHANISM OF DISODIUM ETHYLENEDIAMINETETRAACETATE:
Disodium ethylenediaminetetraacetate is a tetracarboxylate chelating agent that binds polyvalent metal ions (e.g., Ca²⁺, Mg²⁺, Fe³⁺), preventing their interaction in various systems.

✔️ FUNCTIONAL BENEFITS & CHARACTERISTICS OF DISODIUM ETHYLENEDIAMINETETRAACETATE:
Disodium ethylenediaminetetraacetate is used potent chelation of divalent/trivalent metal ions.
Disodium ethylenediaminetetraacetate enhances product stability—prevents oxidation, discoloration, precipitation.

Disodium ethylenediaminetetraacetate is used water-soluble and stable under normal conditions.
Disodium ethylenediaminetetraacetate is used low typical usage concentrations (< 2% in cosmetics; food use limited per regulations).

SYNTHESIS OF DISODIUM ETHYLENEDIAMINETETRAACETATE:
Disodium ethylenediaminetetraacetate was first described in 1935 by Ferdinand Münz, who prepared the compound from ethylenediamine and chloroacetic acid.

Today, Disodium ethylenediaminetetraacetate is mainly synthesised from ethylenediamine (1,2-diaminoethane), formaldehyde, and sodium cyanide.
This route yields the tetrasodium Disodium ethylenediaminetetraacetate, which is converted in a subsequent step into the acid forms:

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

This process is used to produce about 80,000 tonnes of Disodium ethylenediaminetetraacetate each year.
Impurities cogenerated by this route include glycine and nitrilotriacetic acid; they arise from reactions of the ammonia coproduct.

NOMENCLATURE OF DISODIUM ETHYLENEDIAMINETETRAACETATE:
To describe Disodium ethylenediaminetetraacetate and its various protonated forms, chemists distinguish between EDTA4−, the conjugate base that is the ligand, and H4EDTA, the precursor to 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 Disodium ethylenediaminetetraacetate is used to mean H4−xEDTAx−, whereas in its complexes EDTA4− stands for the tetraanion ligand.

PHYSICAL and CHEMICAL PROPERTIES of DISODIUM ETHYLENEDIAMINETETRAACETATE:
CAS Number: 139‑33‑3 (anhydrous), 6381‑92‑6 (dihydrate)
EC Number: 205‑358‑3
IUPAC Name: Disodium N,N′-(ethane-1,2-diyl)bis[N-(carboxymethyl)glycinate] (ethylenediaminetetraacetate disodium salt)
Molecular Formula / Mass: C₁₀H₁₄N₂Na₂O₈ · xH₂O; molar mass ~336.2 g/mol (anhydrous)
Appearance: White, odorless crystalline powder
Melting / Decomposition: ≥ 252–300 °C (decomposes)
Density: ~1.767 g/cm³ @ 20 °C
Water Solubility: ~100–108 g/L at 20 °C

Log P: Highly hydrophilic; log P ~–4.3 to –11.7
Vapor Pressure: ~2×10⁻¹² hPa @ 25 °C
Other: Non-flammable, non-oxidizing, stable solid
Chemical formula: C10H16N2O8
Molar mass: 292.244 g·mol−1
Appearance: Colourless crystals
Density: 0.860 g cm−3 (at 20 °C)
log P: −0.836
Acidity (pKa): 2.0, 2.7, 6.16, 10.26

Thermochemistry
Std enthalpy of formation (ΔfH⦵298): −1765.4 to −1758.0 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298): −4461.7 to −4454.5 kJ mol−
Molecular Weight: 336.21 g/mol
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 10
Rotatable Bond Count: 9
Exact Mass: 336.05455397 Da
Monoisotopic Mass: 336.05455397 Da
Topological Polar Surface Area: 161 Ų

Heavy Atom Count: 22
Formal Charge: 0
Complexity: 336
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 3
Compound Is Canonicalized: Yes

FIRST AID MEASURES of DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of DISODIUM ETHYLENEDIAMINETETRAACETATE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available