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Ethylenediaminetetraacetic acid(CAS No. 60-00-4)

Ethylenediaminetetraacetic acid C10H16N2O8 (cas 60-00-4) Molecular Structure

60-00-4 Structure

Identification and Related Records

【Name】
Ethylenediaminetetraacetic acid
【CAS Registry number】
60-00-4
【Synonyms】
Glycine,N,N'-1,2-ethanediylbis[N-(carboxymethyl)-
Aceticacid, (ethylenedinitrilo)tetra- (8CI)
3,6-Diazaoctanedioic acid,3,6-bis(carboxymethyl)-
Cheelox
Complexon II
EDTA (chelating agent)
Edathamil
Ethylene-N,N'-biscarboxymethyl-N,N'-diglycine
Ethylenediamine-N,N,N',N'-tetraacetic acid
Gluma Cleanser
Havidote
N,N'-1,2-Ethanediyl-bis-N-(carboxymethyl)glycine
Nervanaid B acid
Sequestric acid
Sequestrol
EDTA Acid
【EINECS(EC#)】
200-449-4
【Molecular Formula】
C10H16N2O8 (Products with the same molecular formula)
【Molecular Weight】
292.24
【Inchi】
InChI=1/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)
【Canonical SMILES】
C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O
【MOL File】
60-00-4.mol

Chemical and Physical Properties

【Appearance】
white crystals or powder
【Density】
1.566 g/cm3
【Melting Point】
237-245℃ (dec.)
【Boiling Point】
614.2 °C at 760 mmHg
【Refractive Index】
1.603
【Flash Point】
325.2 °C
【Water】
0.5 g/L (25℃)
【Solubilities】
0.5 g/L (25 °C)
【Color/Form】
Crystals from water
Colorless crystals
【Stability】
Stable. Incompatible with copper, copper alloys, nickel, aluminium, strong oxidizing agents, strong bases
【Storage temp】
2-8°C
【Spectral properties】
IR: 230F (Aldrich Chemical Co., Inc., New York; Aldrich Library of Infrared Spectra, Aldrich Chemical Co., Milwaukee, WI)
NMR: 3:2D (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
【Computed Properties】
Molecular Weight:292.24264 [g/mol]
Molecular Formula:C10H16N2O8
XLogP3-AA:-5.9
H-Bond Donor:4
H-Bond Acceptor:10
Rotatable Bond Count:11
Exact Mass:292.090666
MonoIsotopic Mass:292.090666
Topological Polar Surface Area:156
Heavy Atom Count:20
Formal Charge:0
Complexity:316
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:1
Feature 3D Acceptor Count:8
Feature 3D Anion Count:4
Feature 3D Cation Count:2
Effective Rotor Count:11
Conformer Sampling RMSD:1
CID Conformer Count:17

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Safety】

?Poison by intraperitoneal route. Experimental teratogenic and reproductive effects. Mutation data reported. A general-purpose chelating and complexing agent. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:?Xi
Risk Statements: 36-52/53-36/37/38-36/38
R36:Irritating to eyes.?
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R36/38:Irritating to eyes and skin.
Safety Statements: 26-61-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S37/39:Wear suitable gloves and eye/face protection.?
S36:Wear suitable protective clothing.
WGK Germany: 2
RTECS: AH4025000
F: 3

【Cleanup Methods】
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: Add dilute caustic soda (NaOH). Adjust pH to neutral (pH). Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
【Fire Fighting Procedures】
If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.)
【Reactivities and Incompatibilities】
Reacts violently with lead dioxide.
Reacts with oxidants.
【Other Preventative Measures】
Personnel protection: Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
If material not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
【Specification】

?Chemical Properties of? Edetic acid (CAS NO.60-00-4) is a white crystals or powder, it is?not dissolve in cold water, alcohol and general organic solvents, but is soluble in sodium hydroxide, sodium carbonate and ammonia solution. Reagents commonly used complexing agents, also used as detergents, such as blood anticoagulant, ethylene diamine tetra-acetic acid and formamide cyclization can be obtained. This is a major drug for the treatment of psoriasis. However, as intermediates in organic synthesis is not the primary purpose of?Ethylenediaminetetraacetic acid.?Ethylenediaminetetraacetic acid and its salts with a variety of complex reaction of metal ions to form a stable ring structure, and effectively reduce or suppress the side effects caused by metal ions or harmful effect, is the most widely used metal chelating agents. Edetic acid (CAS NO.60-00-4) and its sodium salt based on the production of raw materials used in different production process is divided into three kinds, namely, chloroacetic acid method, hydrocyanic acid method and sodium cyanide method. Its synonyms?are D([2-(Bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino)-acetic acid ; (ethylenedinitrilo)tetra-aceticaci;(Ethylenedintrilo)tetraacetic acid ; {[2-(Bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetic acid ; 2,2’,2’’,2’’’-(1,2-ethanediyldinitrilo)tetrakis-aceticaci ; 3,6-bis(carboxymethyl)-6-diazaoctanedioicacid ; 3,6-Diazaoctanedioic acid, 3,6-bis(carboxymethyl)- ;?Acetic acid, (ethylenedinitrilo)tetra-? .

【Octanol/Water Partition Coefficient】
log Kow = -3.86 /Estimated/
【Report】

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Ethylenediamine is condensed with sodium monochloroacetate with aid of sodium carbonate. Aqueous solution of reactants is heated to about 90 deg C for 10 hr, then cooled and acidified with hydrochloric acid whereupon the acid precipitates. Salts of acid are known as edetates.
Heating tetrahydroxyethylethylenediamine with sodium hydroxide or potassium hydroxide with calcium oxide catalyst.
The most widely used synthesis is the alkaline cyanomethylation of ethylenediamine by means of sodium cyanide and formaldehyde.
... Commercial method for production of EDTA is the two-step Singer synthesis. In this process, the cyanomethylation step is separate from the hydrolysis. Hydrogen cyanide and formaldehyde react with ethylenediamine to form insoluble (ethylenedinitrilo)tetraacetonitrile (EDTN), 2,2',2'',2'''-(1,2-ethanediyldinitrilo)tetrakis(acetonitrile), in high yield (>96%). The intermediate nitrile is separated, washed, and subsequently hydrolyzed with sodium hydroxide to tetrasodium EDTA, with liberation of byproduct ammonia. Carrying out the synthesis in two stages eliminates most of the impurity-forming reactions and yields a very pure form of chelating agent.
U.S. Exports

(1978) ND
(1982) ND
(1987) ND
U.S. Imports

(1978) ND
(1982) ND
(1987) ND
U.S. Production

(1979) 4.49X10+9 G
(1982) 2.82X10+9 G
(1985) 4.49X10+9 g

Biomedical Effects and Toxicity

【Biological Activity】
Chelating agent; sequesters di- and trivalent metal ions.
【Pharmacological Action】
- Agents that prevent clotting.
- Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.
- Substances which are of little or no nutritive value, but are used in the processing or storage of foods or animal feed, especially in the developed countries; includes ANTIOXIDANTS; FOOD PRESERVATIVES; FOOD COLORING AGENTS; FLAVORING AGENTS; ANTI-INFECTIVE AGENTS (both plain and LOCAL); VEHICLES; EXCIPIENTS and other similarly used substances. Many of the same substances are PHARMACEUTIC AIDS when added to pharmaceuticals rather than to foods.
【Therapeutic Uses】
Anticoagulants; Antidotes; Chelating Agents
MEDICATION (VET): Pharmaceutic aid (chelating agent) in treatment of lead and heavy metal poisoning of farm animals.
Five agents including EDTA were evaluated for their ability to detoxify periodontally involved diseased human tooth root surfaces. Exposure to 15% EDTA partially eliminated the endotoxin. [Sarbinoff J et al; J PERIODONTOL 54 (2): 77-80 (1983)]
【Biomedical Effects and Toxicity】
EDTA is essentially not metabolized by the human body and it is rapidly excreted in the urine. About 50% of EDTA admin iv is excreted within 1 hr and 90% within 7 hr. EDTA and its metal chelates do not permeate the cellular membrane to a significant extent; thus most of the EDTA remains in the extracellular fluids until excreted into the urine.
There is very little metabolic degradation of EDTA The drug is distributed mainly in the extracellular fluids, but very little gains access to the spinal fluid (5%of the plasma concentration).

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 98(SRC), determined from a water solubility of 1,000 mg/L(2) and a regression-derived equation(3), indicates that ethylenediamine tetraacetic acid is expected to have high mobility in soil(SRC). Volatilization of ethylenediamine tetraacetic acid from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant that is estimated as 7.7X10-16 atm-cu m/mol at 25 deg C(SRC), derived from its vapor pressure, 2X10-12 mm Hg at 25 deg C(4), and water solubility, 1,000 mg/L(2). Ethylenediamine tetraacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2X10-12 mm Hg(4). The biodegradation of ethylenediamine tetraacetic acid is negligible under aerobic conditions unless complexed with a metal or subject to an enriched culture of microorganisms(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 98(SRC), determined from a water solubility of 1,000 mg/L(2) and a regression-derived equation(3), indicates that ethylenediamine tetraacetic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant that is estimated as 7.7X10-16 atm-cu m/mol at 25 deg C(SRC), derived from its vapor pressure, 2X10-12 mm Hg at 25 deg C(4), and a water solubility, 1,000 mg/L(2). The pKa of ethylenediamine tetraacetic acid is 0.26(5), indicating that this compound will primarily exist in the dissociated form in water. Therefore, this compound is not expected to adsorb more strongly to organic carbon and clay than its neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 13(SRC), using a water solubility of 1,000 mg/L(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A photolysis half-life of 11.3 minutes for the 1:1 iron(III) complex of ethylenediamine tetraacetic acid was measured using an aqueous solution, illuminated in a Xenotest 1200 apparatus(10). The biodegradation of ethylenediamine tetraacetic acid is negligible under aerobic conditions unless complexed with a metal or subject to an enriched culture of microorganisms(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylenediamine tetraacetic acid, which has a vapor pressure of 2X10-12 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ethylenediamine tetraacetic acid may be removed from the air by wet and dry deposition(SRC).

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