Calcium chloride

From Wikipedia, the free encyclopedia

Jump to: navigation, search Calcium chloride, CaCl2, is a salt of calcium and chlorine. It behaves as a typical ionic halide, and is solid at room temperature. Common applications include brine for refrigeration plants, ice and dust control on roads, and desiccation. Because of its hygroscopic nature, anhydrous calcium chloride must be kept in tightly sealed, airtight containers.

Properties
Calcium chloride can serve as a source of calcium ions in a solution, as calcium chloride is soluble. This property can be useful for displacing ions from solution. For example, phosphate is displaced from solution by calcium: 3 CaCl2 (aq) + 2 K3PO4 (aq) Ca3(PO4)2 (s) + 6 KCl (aq) Molten calcium chloride can be electrolysed to give calcium metal and chlorine gas: CaCl2 (l) Ca (s) + Cl2 (g) Calcium chloride has a very high enthalpy change of solution. The anhydrous salt is deliquescent; it can accumulate enough water in its crystal lattice to form a solution.

[edit] Preparation
Calcium chloride can be produced directly from limestone, but large amounts are also produced as a byproduct of the Solvay process. North American consumption in 2002 was 1,687,000 tons (3.7 billion pounds).[2] A Dow Chemical Company manufacturing facility in Michigan houses about 35% of the total U.S. production capacity for calcium chloride.[3]

[edit] Occurrence
Calcium chloride occurs as the rare evaporite minerals sinjarite (dihydrate) and antarcticite (hexahydrate). A related mineral chlorocalcite (potassium calcium chloride, KCaCl3) is also very rare.

[edit] Uses
[edit] Desiccant

Drying tubes are frequently packed with calcium chloride. Kelp is dried with calcium chloride for use producing sodium carbonate. Adding solid calcium chloride to liquids can remove dissolved water. Calcium chloride is also used in products such as DampRid and Dri-Z-Air which is advertised as an air moisture absorber. Anhydrous calcium chloride has been approved by the FDA as a packaging aid to ensure dryness (CPG 7117.02).[4] These hygroscopic properties are also applied to keep a liquid layer on the surface of the roadway, which holds dust down.[5]

[edit] Deicing and freezing point depression

By depressing the freezing point, calcium chloride is used to usually prevent ice formation and to deice. This is particularly useful on road surfaces. Calcium chloride dissolution is exothermic, and is relatively harmless to plants and soil; however, recent observations in Washington state suggest it may be particularly harsh on roadside evergreen trees.[6] It is also more effective at lower temperatures than sodium chloride. When distributed for this use, it usually takes the form of small, white balls a few millimeters in diameter, called prills. Solutions of calcium chloride can prevent freezing at temperature as low as 52 C (62 F), making it ideal for filling agricultural implement tires as a liquid ballast, aiding traction in cold climates.[7]

[edit] Source of calcium ions

Calcium chloride is used to increase the hardness in swimming pools and piscines. This reduces the erosion of the concrete in the pool. By Le Chatelier's principle and the common ion effect, increasing the concentration of calcium in the water will reduce the dissolution of calcium compounds essential to the structure of concrete.[citation needed] In marine aquariums, calcium chloride is added to introduce bioavailable calcium for calcium carbonate-shelled animals such as mollusks and cnidarians. Calcium hydroxide (kalkwasser mix) or a calcium reactor can also be used to introduce calcium, however calcium chloride addition is the fastest method and has minimal impact on pH.

[edit] Food
As an ingredient, it is listed as a permitted food additive in the European Union for use as a sequestrant and firming agent with the E number E509, and considered as generally recognized as safe (GRAS) by the U.S. Food and Drug Administration.[8] The average intake of calcium chloride as food additives has been estimated to be 160345 mg/day for individuals.[9] As a firming agent, calcium chloride is used in canned vegetables, in firming soybean curds into tofu and in producing a caviar substitute from vegetable or fruit juices.[10] It is commonly used as an electrolyte in sports drinks and other beverages, including bottled water. The extremely salty taste of calcium chloride is used to flavor pickles while not increasing the food's sodium content. Calcium chloride's freezing-point

depression properties are used to slow the freezing of the caramel in caramel-filled chocolate bars. In brewing beer, calcium chloride is sometimes used to correct mineral deficiencies in the brewing water. It affects flavor and chemical reactions during the brewing process, and can also affect yeast function during fermentation. Calcium chloride is sometimes added to processed milk to restore the natural balance between calcium and protein in casein for the purposes of making cheeses, such as brie, Plardon and Stilton. Finally, it is frequently added to sliced apples to maintain texture.

[edit] Medicine
Calcium chloride can be injected as intravenous therapy for the treatment of hypocalcaemia. It can be used for magnesium intoxication. Calcium chloride injection may antagonize cardiac toxicity as measured by electrocardiogram. It can help to protect the myocardium from dangerously high levels of serum potassium in hyperkalemia. Calcium chloride can be used to quickly treat calcium channel blocker toxicity, from the side effects of drugs such as diltiazem (Cardizem) helping avoid potential heart attacks. [11] Aqueous calcium chloride is used in genetic transformation of cells by increasing the cell membrane permeability, inducing competence for DNA uptake (allowing DNA fragments to enter the cell more readily).

[edit] Other
Calcium chloride is used in concrete mixes to help speed up the initial setting, but chloride ions lead to corrosion of steel rebar, so it should not be used in reinforced concrete.[12] The anhydrous form of calcium chloride may also be used for this purpose and can provide a measure of the moisture in concrete.[13] Calcium chloride is used in swimming pool water as a pH buffer and to adjust the calcium hardness of the water. Calcium chloride is included as an additive in plastics and in fire extinguishers, in wastewater treatment as a drainage aid, in blast furnaces as an additive to control scaffolding (clumping and adhesion of materials that prevent the furnace charge from descending), and in fabric softener as a thinner. The exothermic dissolution of calcium chloride is used in self-heating cans and heating pads. In the oil industry, calcium chloride is used to increase the density of solids-free brines. It is also used to provide inhibition of swelling clays in the water phase of invert emulsion drilling fluids.

[edit] Toxicology

Calcium chloride can act as an irritant by desiccating moist skin. Solid calcium chloride dissolves exothermically, and burns can result in the mouth and esophagus if it is ingested. Ingestion of concentrated solutions or solid products may cause gastrointestinal irritation or ulceration.[14]

[edit] See also

Calcium(I) chloride Calcium chloride transformation

Ethylenediaminetetraacetic acid
From Wikipedia, the free encyclopedia

Jump to: navigation, search "EDTA" redirects here. For other uses, see EDTA (disambiguation).

Ethylenediaminetetraacetic acid

Preferred IUPAC name[hide] 2,2',2'',2'''-(Ethane-1,2-diyldinitrilo)tetraacetic acid Systematic name[hide] 2-({2[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid Other names[hide] Diaminoethane-tetraacetic acid Edetic acid Ethylenedinitrilo-tetraacetic acid Versene

Identifiers

Abbreviations CAS number PubChem ChemSpider UNII EC number UN number DrugBank KEGG MeSH ChEBI ChEMBL RTECS number ATC code

EDTA H4EDTA 60-00-4 , 15251-22-6 (2H),(2H),(2H) 6049 , 46781544 (13C),(13C),(1-13C) , 16217600 (2H),(2H),(2H) 5826 , 17345117 (2H),(2H),(2H) 9G34HU7RV0 200-449-4 3077 DB00974 D00052 Edetic+acid CHEBI:42191 CHEMBL858 AH4025000 V03AB03
[U.S.FDA]

Beilstein Reference 1716295 Jmol-3D images Image 1 SMILES

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InChI
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Properties Molecular formula C10H16N2O8 Molar mass Density Melting point 292.24 g mol1 0.86 g cm3 237-245 C, 510-518 K, 459-473 F (dec.)

pKa1 = 0.0 (CO2H) ( = 1.0) pKa2 = 1.5 (CO2H) ( = 0.1) Acidity (pKa) pKa3 = 2.00 (CO2H) ( = 0.1) pKa4 = 2.69 (CO2H) ( = 0.1) pKa5 = 6.13 (NH+) ( = 0.1) pKa6 = 10.37 (NH+) ( = 0.1)[1] Hazards MSDS R-phrases S-phrases Main hazards External MSDS R36 S26 irritant

NFPA 704

0 1 0
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Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

Ethylenediaminetetraacetic acid, widely abbreviated as EDTA (for other names, see Table), is a polyamino carboxylic acid and a colourless, water-soluble solid. Its conjugate base is named ethylenediaminetetraacetate. It is widely used to dissolve limescale. Its usefulness arises because of its role as a hexadentate ("six-toothed") ligand and chelating agent, i.e. its ability to "sequester" metal ions such as Ca2+ and Fe3+. After being bound by EDTA, metal ions remain in solution but exhibit diminished reactivity. EDTA is produced as several salts, notably disodium EDTA and calcium disodium EDTA.

Contents
[hide]

1 Synthesis 2 Nomenclature 3 Coordination chemistry principles 4 Uses

4.1 Industry 4.2 Medicine 4.3 Laboratory applications 5 Toxicity and environmental considerations 6 Methods of detection and analysis 7 See also 8 Notes and references 9 External links

o o o

[edit] Synthesis
The compound was first described in 1935 by Ferdinand Munz, who prepared the compound from ethylenediamine and chloroacetic acid.[2] Today, EDTA is mainly synthesised from ethylenediamine (1,2-diaminoethane), formaldehyde, and sodium cyanide.[3] This route yields the sodium salt, which can be 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 In this way, about 80M kilograms are produced each year. Impurities cogenerated by this route include glycine and nitrilotriacetic acid; they arise from reactions of the ammonia coproduct.[4]

[edit] Nomenclature
To describe EDTA 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 Y4 form is prevalent. In this article, the term EDTA is used to mean H4-xEDTAx-, whereas in its complexes EDTA4- stands for the tetra-deprotonated ligand.

[edit] Coordination chemistry principles

Metal-EDTA chelate In coordination chemistry, EDTA4- is a member of the polyamino carboxylic acid family of ligands. EDTA4- usually binds to a metal cation through its two amines and four carboxylates. Many of the resulting coordination compounds adopt octahedral geometry. Although of little consequence for its applications, these octahedral complexes are chiral. The anion [Co(EDTA)] has been resolved into enantiomers.[5] Many complexes of EDTA4- adopt more complex structures due to (i) the formation of an additional bond to water, i.e. seven-coordinate complexes, or (ii) the displacement of one carboxylate arm by water. Early work on the development of EDTA was undertaken by Gerold Schwarzenbach in the 1940s.[6] EDTA forms especially strong complexes with Mn(II), Cu(II), Fe(III), Pb (II) and Co(III).[7] Several features of EDTA'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 = 1025.1)

Written in this way, the equilibrium quotient shows that metal ions compete with protons for binding to EDTA. Because metal ions are extensively enveloped by EDTA, their catalytic properties are often suppressed. Finally, since complexes of EDTA4- are anionic, they tend to be highly soluble in water. For this reason, EDTA is able to dissolve deposits of metal oxides and carbonates.

[edit] Uses
[edit] Industry
In industry, EDTA is mainly used to sequester metal ions in aqueous solution. In the textile industry, it prevents metal ion impurities from modifying colours of dyed products. In the pulp and paper industry, EDTA inhibits the ability of metal ions, especially Mn2+, from catalyzing the disproportionation of hydrogen peroxide, which is used in "chlorine-free bleaching." In a similar manner, EDTA is added to some food as a preservative or stabilizer to prevent catalytic oxidative decoloration, which is catalyzed by metal ions.[8] In personal care products, it is added to cosmetics to improve their stability toward air.[9] In soft drinks containing ascorbic acid and sodium benzoate, EDTA mitigates formation of benzene (a carcinogen).[10]

The reduction of water hardness in laundry applications and the dissolution of scale in boilers both rely on EDTA and related complexants to bind Ca2+, Mg2+, as well as other metal ions. Once bound to EDTA, these metal centers tend not to form precipitates or to interfere with the action of the soaps and detergents. For similar reasons, cleaning solutions often contain EDTA. The solubilization of ferric ions near neutral pH is accomplished using EDTA. This property is useful in agriculture including hydroponics, especially in calcareous soils. Otherwise, at near-neutral pH, iron(III) forms insoluble salts, which are less bioavailable. Aqueous [Fe(edta)]- is used for removing ("scrubbing") hydrogen sulfide from gas streams. This conversion is achieved by oxidizing the hydrogen sulfur to elemental sulfur, which is non-volatile: 2 [Fe(edta)]- + H2S 2 [Fe(edta)]2 + S + 2 H+ In this application, the ferric center is reduced to its ferrous derivative, which can then be reoxidized by air. In similar manner, nitrogen oxides are removed from gas streams using [Fe(edta)]2-. The oxidizing properties of [Fe(edta)]- are also exploited in photography, where it is used to solubilize silver particles.[4] EDTA was used in the 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 EDTA complexes with atomic number. Using sulfonated polystyrene beads and copper(II) as a retaining ion, EDTA causes the lanthanides to migrate down the column of resin while separating into bands of pure lanthanide. The lanthanides elute in order of decreasing atomic number. Due to the expense of this method, relative to counter-current solvent extraction, ionexchange is now used only to obtain the highest purities of lanthanide (typically greater than 4N, 99.99%).[citation needed]

[edit] Medicine
EDTA is used to bind metal ions in the practice of chelation therapy, e.g., for treating mercury and lead poisoning.[11] It 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. Alternative medical practitioners believe EDTA acts as a powerful antioxidant to prevent free radicals from injuring blood vessel walls, therefore reducing atherosclerosis.[12] The U.S. FDA approved the use of EDTA for lead poisoning[13] on July 16, 1953, under the brand name of Versenate[14], which was licensed to the pharmaceutical company Riker. It has not approved it for the treatment of atherosclerosis.[15] Dentists and endodontists use EDTA solutions to remove inorganic debris (smear layer) and lubricate the canals in endodontics. This procedure helps prepare root canals for obturation. Furthermore, EDTA solutions with the addition of a surfactant loosen up calcifications inside a root canal and allow instrumentation (canals shaping) and facilitate apical advancement of a file in a tight/calcified root canal towards the apex. It serves as a preservative (usually to enhance the action of another preservative such as benzalkonium chloride or thiomersal) in ocular preparations and eyedrops.[16] In evaluating kidney function, the complex [Cr(edta)]- is administered intravenously

and its filtration into the urine is monitored. This method is useful for evaluating glomerular filtration rate.[17] EDTA is used extensively in the analysis of blood. It is an anticoagulant for blood samples for CBC/FBEs. Laboratory studies also suggest that EDTA chelation may prevent collection of platelets on the lining of the vessel [such as arteries] (which can otherwise lead to formation of blood clots, which itself is associated with atheromatous plaque formation or rupture, and thereby ultimately disrupts blood flow). These ideas have so far been proven ineffective;[18] however, a major clinical study of the effects of EDTA on coronary arteries is currently (2008) proceeding.[19] EDTA played a role in the O.J. Simpson trial when the defense alleged that one of the blood samples collected from Simpson's estate was found to contain traces of the compound.[20] EDTA is a slime dispersant, and has been found to be highly effective in reducing bacterial growth during implantation of intraocular lenses (IOLs).[21]

[edit] Laboratory applications

In the laboratory, EDTA 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 or proteins. In analytical chemistry, EDTA 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. EDTA finds many specialized uses in the biomedical laboratories, such as in veterinary ophthalmology as an anticollagenase to prevent the worsening of corneal ulcers in animals. In tissue culture EDTA 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, EDTA can be used as a decalcifying agent making it possible to cut sections using a microtome once the tissue sample is demineralised. EDTA 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.[22]

[edit] Toxicity and environmental considerations

EDTA is in such widespread use that it has emerged as a persistent organic pollutant.[23] It degrades to ethylenediaminetriacetic acid, which then cyclizes to the diketopiperizide, a cumulative, persistent, organic environmental pollutant. An alternative chelating agent with fewer environmental pollution implications is EDDS. EDTA exhibits low acute toxicity with LD50 (rat) of 2.0 2.2 g/kg.[4] It has been found to be both cytotoxic and weakly genotoxic in laboratory animals. Oral exposures have been noted to cause reproductive and developmental effects.[9] The same study by Lanigan[9] also found that both dermal exposure to EDTA in most cosmetic formulations and inhalation exposure to EDTA in aerosolized cosmetic formulations would produce exposure levels below those seen to be toxic in oral dosing studies.

[edit] 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 7.3 ng/mL in human plasma and a quantitation limit of 15 ng/mL.[24] This method works with sample volumes as small as ~7-8 nL.[24] EDTA has also been measured in non-alcoholic beverages using high performance liquid chromatography (HPLC) at a level of 2.0 g/mL.[25][26]

[edit] See also

DTPA EGTA BAPTA

EGTA (chemical)
From Wikipedia, the free encyclopedia

Jump to: navigation, search

EGTA (chemical)

IUPAC name[hide] ethylene glycol-bis(2-aminoethylether)-N,N,N,N-tetraacetic acid

Identifiers CAS number PubChem ChemSpider UNII KEGG ChEBI 67-42-5 6207 5972 526U7A2651 D00569 CHEBI:30740

ChEMBL Jmol-3D images

CHEMBL240390 Image 1 SMILES

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InChI
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Properties Molecular formula Molar mass Melting point C14H24N2O10 380.35 g/mol 241 C, 514 K, 466 F (verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

EGTA (ethylene glycol tetraacetic acid) is a polyamino carboxylic acid, a chelating agent that is related to the better known EDTA, but with a much higher affinity for calcium than for magnesium ions. It is useful for making buffer solutions that resemble the environment inside living cells[1] where calcium ions are usually at least a thousandfold less concentrated than magnesium. The pKa for binding of calcium ions by tetrabasic EGTA is 11.00, but the protonated forms do not significantly contribute to binding, so at pH 7, the apparent pKa becomes 6.91. See Qin et al. for an example of a pKa calculation.[2] EGTA has also been used experimentally for the treatment of animals with cerium poisoning and for the separation of thorium from the mineral monazite. EGTA is used as a compound in elution buffer in the protein purification technique known as Tandem Affinity Purification (TAP), in which recombinant fusion proteins are bound to calmodulin beads and eluted out by adding EGTA. EGTA is often employed in dentistry and endodontics for the removal of smear layer.

[edit] See also

EDTA

BAPTA

[edit] References
This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (October 2007)
1. ^ Bett, Glenna C. L.; Rasmusson, Randall L. (2002). "1. Computer Models of Ion Channels". In Cabo, Candido; Rosenbaum, David S.. Quantitative Cardiac Electrophysiology. Marcel Dekker. p. 48. ISBN 0-8247-0774-5. 2. ^ Ning Qin, Riccardo Olcese, Michael Bransby, Tony Lin, and Lutz Birnbaumer (March 1999). "Ca2+-induced inhibition of the cardiac Ca2+ channel depends on calmodulin". PNAS 96 (5): 24352438. doi:10.1073/pnas.96.5.2435. PMC 26802. PMID 10051660. http://www.pnas.org/cgi/content/full/96/5/2435. Retrieved 200710-22.