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Chelation is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds , but this is not a necessity.

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49-514: Dreft is a laundry detergent in the United States , Canada , United Kingdom and other markets. First produced by Procter & Gamble in 1933, it was the first synthetic detergent. The Fairy brand of washing-up liquid and Cascade brand of dishwasher detergent are also sold under the name "Dreft" in some countries, including the Netherlands and Belgium. In Canada, the laundry detergent

98-433: A humic acid or a protein). Thus, metal chelates are relevant to the mobilization of metals in the soil , the uptake and the accumulation of metals into plants and microorganisms . Selective chelation of heavy metals is relevant to bioremediation (e.g., removal of Cs from radioactive waste ). Synthetic chelates such as ethylenediaminetetraacetic acid (EDTA) proved too stable and not nutritionally viable. If

147-410: A mole ratio in the range of 1–3 (preferably 2) moles of amino acids for one mole of metal. The average weight of the hydrolyzed amino acids must be approximately 150 and the resulting molecular weight of the chelate must not exceed 800  Da . Since the early development of these compounds, much more research has been conducted, and has been applied to human nutrition products in a similar manner to

196-470: A 30–35% market share in western Europe. According to Lubrizol , the powdered detergent market is growing by 2 percent annually. Phosphates in detergent became an environmental concern in the 1950s and the subject of bans in later years. Phosphates make laundry cleaner but also cause eutrophication , particularly with poor wastewater treatment . A 2013 academic study of fragranced laundry products found "more than 25 VOCs emitted from dryer vents, with

245-469: A chelate complex with the copper ion. Chelation results in the formation of a five-membered CuC 2 N 2 ring. In ( 2 ) the bidentate ligand is replaced by two monodentate methylamine ligands of approximately the same donor power, indicating that the Cu–N bonds are approximately the same in the two reactions. The thermodynamic approach to describing the chelate effect considers the equilibrium constant for

294-790: A chemical viewpoint, soils can be grouped into: Soils difficult to remove are pigments and dyes , fats , resins , tar , waxes , and denatured protein . Laundry detergents may contain builders (50% by weight, approximately), surfactants (15%), bleach (7%), enzymes (2%), soil antideposition agents, foam regulators, corrosion inhibitors , optical brighteners , dye transfer inhibitors , fragrances , dyes , fillers and formulation aids. Builders (also called chelating or sequestering agents ) are water softeners . Most domestic water supplies contain some dissolved minerals, especially in hard water areas. The metal cations present in these dissolved minerals, particularly calcium and magnesium ions, can react with surfactants to form soap scum which

343-436: A combination of various surfactants to balance their performance. Until the 1950s, soap was the predominant surfactant in laundry detergents. By the end of the 1950s so-called "synthetic detergents" (syndets) like branched alkylbenzene sulfonates had largely replaced soap in developed countries. Due to their poor biodegradability these branched alkylbenzenesulfonates were replaced with linear alkylbenzenesulfonates (LAS) in

392-405: A different type of enzyme: proteases ( savinase ) for proteins, lipases for greases, α-amylases for carbohydrates, and cellulases for cellulose. Many other ingredients are added depending on the expected circumstances of use. Such additives modify the foaming properties of the product by either stabilizing or counteracting foam. Other ingredients increase or decrease the viscosity of

441-448: Is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder ( washing powder ) and liquid form. While powdered and liquid detergents hold roughly equal share of the worldwide laundry detergent market in terms of value , powdered detergents are sold twice as much compared to liquids in terms of volume . From ancient times, chemical additives were used to facilitate

490-576: Is an antidote for poisoning by mercury , arsenic , and lead . Chelating agents convert these metal ions into a chemically and biochemically inert form that can be excreted. Chelation using calcium disodium EDTA has been approved by the U.S. Food and Drug Administration (FDA) for serious cases of lead poisoning . It is not approved for treating " heavy metal toxicity ". Although beneficial in cases of serious lead poisoning, use of disodium EDTA (edetate disodium) instead of calcium disodium EDTA has resulted in fatalities due to hypocalcemia . Disodium EDTA

539-458: Is clear that the chelate effect is predominantly an effect of entropy. Other explanations, including that of Schwarzenbach , are discussed in Greenwood and Earnshaw ( loc.cit ). Numerous biomolecules exhibit the ability to dissolve certain metal cations . Thus, proteins , polysaccharides , and polynucleic acids are excellent polydentate ligands for many metal ions. Organic compounds such as

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588-478: Is insufficiently active as a bleach at temperature below 60 °C (140 °F), which traditionally made hot washes the norm. The development of bleach activators in the 1970s and 1980s allowed for cooler washing temperatures to be effective. These compounds, such as tetraacetylethylenediamine (TAED), react with hydrogen peroxide to produce peracetic acid , which is an even more effective bleach, particularly at lower temperatures. The use of enzymes for laundry

637-666: Is more widely used. In 2018, sales of powdered detergent measured 14 million metric tons , double that of liquids. While liquid detergent is widely used in many Western countries, powdered detergent is popular in Africa, India, China, Latin America, and other emerging markets . Powders also hold significant market share in eastern Europe and in some western European countries due to their advantage over liquids in whitening clothes. According to Desmet Ballestra, designer and builder of chemical plants and detergent-making equipment, powdered detergents have

686-499: Is much less effective for cleaning and can precipitate onto both fabric and washing machine components. Builders remove mineral ions responsible for hard water through precipitation , chelation , or ion exchange . In addition, they help remove soil by dispersion . The earliest builders were sodium carbonate (washing soda) and sodium silicate (waterglass). In the 1930s phosphates ( sodium phosphates ) and polyphosphates ( sodium hexametaphosphate ) were introduced, continuing with

735-629: Is not approved by the FDA for any use, and all FDA-approved chelation therapy products require a prescription. Chelate complexes of gadolinium are often used as contrast agents in MRI scans , although iron particle and manganese chelate complexes have also been explored. Bifunctional chelate complexes of zirconium , gallium , fluorine , copper , yttrium , bromine , or iodine are often used for conjugation to monoclonal antibodies for use in antibody-based PET imaging . These chelate complexes often employ

784-430: Is sold under the brand name Ivory Snow . Synthetic detergents represented an improvement in laundry washing because these synthetic materials are less susceptible to hard water. The commercial availability of fatty alcohols opened the way for the production of the related organosulfate derivatives. In Germany, BASF started selling FeWA, followed by Dreft in the following year. By 1947, Dreft dishwashing detergent

833-534: Is the same in both reactions, the concentration [Cu(en)] is much higher than the concentration [Cu(MeNH 2 ) 2 ] because β 11 ≫ β 12 . An equilibrium constant, K , is related to the standard Gibbs free energy , ⁠ Δ G ⊖ {\displaystyle \Delta G^{\ominus }} ⁠ by where R is the gas constant and T is the temperature in kelvins . ⁠ Δ H ⊖ {\displaystyle \Delta H^{\ominus }} ⁠

882-410: Is the standard enthalpy change of the reaction and ⁠ Δ S ⊖ {\displaystyle \Delta S^{\ominus }} ⁠ is the standard entropy change. Since the enthalpy should be approximately the same for the two reactions, the difference between the two stability constants is due to the effects of entropy. In equation ( 1 ) there are two particles on

931-477: Is the typical chelating agent that keeps these metal ions in a soluble form. Because of their wide needs, the overall chelating agents growth was 4% annually during 2009–2014 and the trend is likely to increase. Aminopolycarboxylic acids chelators are the most widely consumed chelating agents; however, the percentage of the greener alternative chelators in this category continues to grow. The consumption of traditional aminopolycarboxylates chelators, in particular

980-404: Is used to soften water in soaps and laundry detergents . A common synthetic chelator is EDTA . Phosphonates are also well-known chelating agents. Chelators are used in water treatment programs and specifically in steam engineering . Although the treatment is often referred to as "softening", chelation has little effect on the water's mineral content, other than to make it soluble and lower

1029-454: The Dopa residues in mussel foot protein-1 to improve the strength of the threads that they use to secure themselves to surfaces. In earth science, chemical weathering is attributed to organic chelating agents (e.g., peptides and sugars ) that extract metal ions from minerals and rocks. Most metal complexes in the environment and in nature are bound in some form of chelate ring (e.g., with

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1078-489: The cornea , allowing for some increase in clarity of vision for the patient. Homogeneous catalysts are often chelated complexes. A representative example is the use of BINAP (a bidentate phosphine ) in Noyori asymmetric hydrogenation and asymmetric isomerization. The latter has the practical use of manufacture of synthetic (–)-menthol . A chelating agent is the main component of some rust removal formulations. Citric acid

1127-453: The pH of the wash. Hydrophilic fibers like cotton will naturally have a negative surface charge in water, whereas synthetic fibers are comparatively neutral. The negative charge is further increased by the adsorption of anionic surfactants. With increasing pH, soil and fibers become more negatively charged, resulting in increased mutual repulsion. The optimum pH range for good detergency is 9–10.5. Alkalis may also enhance wash performance via

1176-426: The porphyrin rings in hemoglobin and chlorophyll . Many microbial species produce water-soluble pigments that serve as chelating agents, termed siderophores . For example, species of Pseudomonas are known to secrete pyochelin and pyoverdine that bind iron. Enterobactin , produced by E. coli , is the strongest chelating agent known. The marine mussels use metal chelation, especially Fe chelation with

1225-423: The saponification of fats. Builder and surfactant work synergistically to achieve soil removal, and the washing effect of the builder may exceed that of the surfactant. With hydrophilic fibers like cotton , wool , polyamide and polyacrylonitrile , sodium triphosphate removes soil more effectively than a surfactant alone. It is expected that when washing hydrophobic fibers like polyesters and polyolefins ,

1274-784: The EDTA ( ethylenediaminetetraacetic acid ) and NTA ( nitrilotriacetic acid ), is declining (−6% annually), because of the persisting concerns over their toxicity and negative environmental impact. In 2013, these greener alternative chelants represented approximately 15% of the total aminopolycarboxylic acids demand. This is expected to rise to around 21% by 2018, replacing and aminophosphonic acids used in cleaning applications. Examples of some Greener alternative chelating agents include ethylenediamine disuccinic acid (EDDS), polyaspartic acid (PASA), methylglycinediacetic acid (MGDA), glutamic diacetic acid (L-GLDA), citrate , gluconic acid , amino acids, plant extracts etc. Dechelation (or de-chelation)

1323-473: The Netherlands, Norway, Sweden, Switzerland, United States, Canada, and Japan. Chelation The word chelation is derived from Greek χηλή, chēlē , meaning "claw"; the ligands lie around the central atom like the claws of a crab . The term chelate was first applied in 1920 by Sir Gilbert T. Morgan and H. D. K. Drew, who stated: "The adjective chelate, derived from the great claw or chele (Greek) of

1372-443: The amino acids glutamic acid and histidine , organic diacids such as malate , and polypeptides such as phytochelatin are also typical chelators. In addition to these adventitious chelators, several biomolecules are specifically produced to bind certain metals (see next section). Virtually all metalloenzymes feature metals that are chelated, usually to peptides or cofactors and prosthetic groups. Such chelating agents include

1421-401: The animal nutrition experiments that pioneered the technology. Ferrous bis-glycinate is an example of one of these compounds that has been developed for human nutrition. Dentin adhesives were first designed and produced in the 1950s based on a co-monomer chelate with calcium on the surface of the tooth and generated very weak water-resistant chemical bonding (2–3 MPa). Chelation therapy

1470-482: The commercially important German brand FEWA, produced by BASF , and Dreft , the U.S. brand produced by Procter & Gamble . Such detergents were mainly used in industry until after World War II . By then, new developments and the later conversion of aviation fuel plants to produce tetrapropylene , used in household detergents production, caused a fast growth of domestic use in the late 1940s. Washing laundry involves removing mixed soils from fiber surfaces. From

1519-455: The crab or other crustaceans, is suggested for the caliperlike groups which function as two associating units and fasten to the central atom so as to produce heterocyclic rings." Chelation is useful in applications such as providing nutritional supplements, in chelation therapy to remove toxic metals from the body, as contrast agents in MRI scanning , in manufacturing using homogeneous catalysts , in chemical water treatment to assist in

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1568-401: The effect are shown in the following table. These data confirm that the enthalpy changes are approximately equal for the two reactions and that the main reason for the greater stability of the chelate complex is the entropy term, which is much less unfavorable. In general it is difficult to account precisely for thermodynamic values in terms of changes in solution at the molecular level, but it

1617-740: The effectiveness of the surfactant surpasses that of the builder, however this is not the case. Surfactants are responsible for most of the cleaning performance in laundry detergent. They provide this by absorption and emulsification of soil into the water and also by reducing the water's surface tension to improve wetting . Laundry detergents contain mostly anionic and non-ionic surfactants. Cationic surfactants are normally incompatible with anionic detergents and have poor cleaning efficiency; they are employed only for certain special effects, as fabric softeners , antistatic agents , and biocides . Zwitterionic surfactants are rarely employed in laundry detergents mainly for cost reasons. Most detergents use

1666-436: The highest concentrations of acetaldehyde, acetone, and ethanol. Seven of these VOCs are classified as hazardous air pollutants (HAPs) and two as carcinogenic HAPs (acetaldehyde and benzene)". The EEC Directive 73/404/EEC stipulates an average biodegradability of at least 90% for all types of surfactants used in detergents. The phosphate content of detergents is regulated in many countries, e.g., Austria, Germany, Italy,

1715-413: The intestinal tract is a cause of numerous interactions between drugs and metal ions (also known as " minerals " in nutrition). As examples, antibiotic drugs of the tetracycline and quinolone families are chelators of Fe , Ca , and Mg ions. EDTA, which binds to calcium, is used to alleviate the hypercalcemia that often results from band keratopathy . The calcium may then be removed from

1764-577: The introduction of phosphonates ( HEDP , ATMP , EDTMP ). While these phosphorus-based agents are generally non-toxic they are now known to cause nutrient pollution , which can have serious environmental consequences. As such they have been banned in many countries, leading to the development of phosphorus-free agents, such as polycarboxylates ( EDTA , NTA ), citrates ( trisodium citrate ), silicates ( sodium silicate ), gluconic acid and polyacrylic acid ; or ion exchange agents like zeolites . Alkali builders may also enhance performance by changing

1813-459: The left and one on the right, whereas in equation ( 2 ) there are three particles on the left and one on the right. This difference means that less entropy of disorder is lost when the chelate complex is formed with bidentate ligand than when the complex with monodentate ligands is formed. This is one of the factors contributing to the entropy difference. Other factors include solvation changes and ring formation. Some experimental data to illustrate

1862-587: The mechanical washing of textile fibers with water. The earliest recorded evidence of the production of soap-like materials dates back to around 2800 BC in ancient Babylon . German chemical companies developed an alkyl sulfate surfactant in 1917, in response to shortages of soap ingredients during the Allied Blockade of Germany  during World War I . In the 1930s, commercially viable routes to fatty alcohols were developed, and these new materials were converted to their sulfate esters , key ingredients in

1911-904: The mid-1960s. Since the 1980s, alkyl sulfates such as SDS have found increasing application at the expense of LAS. Since the 1970s, nonionic surfactants like alcohol ethoxylates have acquired a higher share in laundry detergents. In the 1990s, glucamides appeared as co-surfactants, and alkyl polyglycosides have been used in specialty detergents for fine fabrics. Despite the name, modern laundry bleaches do not include household bleach ( sodium hypochlorite ). Laundry bleaches are typically stable adducts of hydrogen peroxide , such as sodium perborate and sodium percarbonate ; these are inactive as solids but will release hydrogen peroxide upon exposure to water. The main targets of bleaches are oxidisible organic stains, which are usually of vegetable origin (e.g. chlorophyll , anthocyanin dyes, tannins , humic acids , and carotenoid pigments). Hydrogen peroxide

1960-486: The mineral was taken from the EDTA ligand, the ligand could not be used by the body and would be expelled. During the expulsion process, the EDTA ligand randomly chelated and stripped other minerals from the body. According to the Association of American Feed Control Officials (AAFCO), a metal–amino acid chelate is defined as the product resulting from the reaction of metal ions from a soluble metal salt with amino acids, with

2009-492: The other components and do not affect the color of the cleaned item. The perfumes are typically a mixture of many compounds , common classes include terpene alcohols ( citronellol , geraniol , linalool , nerol ) and their esters ( linalyl acetate ), aromatic aldehydes ( helional , hexyl cinnamaldehyde , lilial ) and synthetic musks ( galaxolide ). Worldwide, while liquid and powdered detergents hold roughly equal market share in terms of value, powdered laundry detergent

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2058-517: The product being cleaned. Commercial or industrial laundries may make use of a laundry sour during the final rinse cycle to neutralise any remaining alkali surfactants and remove acid-sensitive stains. A number of ingredients affect aesthetic properties of the item to be cleaned or the detergent itself before or during use. These agents include optical brighteners , fabric softeners , and colorants. A variety of perfumes are also components of modern detergents, provided that they are compatible with

2107-421: The reaction: the larger the equilibrium constant, the higher the concentration of the complex. Electrical charges have been omitted for simplicity of notation. The square brackets indicate concentration, and the subscripts to the stability constants , β , indicate the stoichiometry of the complex. When the analytical concentration of methylamine is twice that of ethylenediamine and the concentration of copper

2156-412: The removal of metals, and in fertilizers . The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate) ligands for the same metal. The thermodynamic principles underpinning the chelate effect are illustrated by the contrasting affinities of copper (II) for ethylenediamine (en) vs. methylamine . In ( 1 ) the ethylenediamine forms

2205-428: The solution, or solubilize other ingredients. Corrosion inhibitors counteract damage to washing equipment. Dye transfer inhibitors prevent dyes from one article from coloring other items, these are generally polar water-soluble polymers such as polyvinylpyrrolidone , to which the dyes preferentially bind. Antiredeposition agents such as carboxymethyl cellulose are used to prevent fine soil particles from reattaching to

2254-501: The usage of hexadentate ligands such as desferrioxamine B (DFO), according to Meijs et al. , and the gadolinium complexes often employ the usage of octadentate ligands such as DTPA, according to Desreux et al . Auranofin , a chelate complex of gold , is used in the treatment of rheumatoid arthritis, and penicillamine , which forms chelate complexes of copper , is used in the treatment of Wilson's disease and cystinuria , as well as refractory rheumatoid arthritis. Chelation in

2303-406: The water's pH level. Metal chelate compounds are common components of fertilizers to provide micronutrients. These micronutrients (manganese, iron, zinc, copper) are required for the health of the plants. Most fertilizers contain phosphate salts that, in the absence of chelating agents, typically convert these metal ions into insoluble solids that are of no nutritional value to the plants. EDTA

2352-600: Was introduced in 1913 by Otto Rohm . The first preparation was a pancreatic extract obtained from slaughtered animals, which was unstable against alkali and bleach. Only in the latter part of the century with the availability of thermally robust bacterial enzymes did this technology become mainstream. Enzymes are required to degrade stubborn stains composed of proteins (e.g., milk, cocoa, blood, egg yolk, grass), fats (e.g., chocolate, fats, oils), starch (e.g., flour and potato stains), and cellulose (damaged cotton fibrils , vegetable and fruit stains). Each type of stain requires

2401-416: Was released. Since the 1940s, hypoallergenic formulations of Dreft ("Dreft Stage 1" and "Dreft Stage 2") have been advertised as an ideal laundry detergent for washing baby linens. The slogan for Dreft is "For a Clean You Can Trust". It is generally marketed to mothers of newborns. This product article is a stub . You can help Misplaced Pages by expanding it . Laundry detergent Laundry detergent

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