EDDS

Last updated
EDDS
2,2'-(ethane-1,2-diylbis(azanediyl))disuccinic acid 200.svg
Names
IUPAC name
Ethylenediamine-N,N′-disuccinic acid[ citation needed ]
Identifiers
3D model (JSmol)
ChemSpider
  • 109992  X mark.svgN
  • 9489961 2-[(2-{[(1S)-1-Carboxyethyl]amino}ethyl)amino] X mark.svgN
  • 8283888 (2R)-2-[(2-{[(1R)-1-Carboxyethyl]amino}ethyl)amino] X mark.svgN
  • 435376 (2S)-2-[(2-{[(1S)-1-Carboxyethyl]amino}ethyl)amino] X mark.svgN
MeSH N,N'-ethylenediamine+disuccinic+acid
PubChem CID
  • 123395
  • 11314994  2-[(2-{[(1S)-1-Carboxyethyl]amino}ethyl)amino]
  • 10108362  (2R)-2-[(2-{[(1R)-1-Carboxyethyl]amino}ethyl)amino]
  • 497266  (2S)-2-[(2-{[(1S)-1-Carboxyethyl]amino}ethyl)amino]
  • 46218600  (2S)-2-[(2-{[(1R)-1-Carboxyethyl]amino}ethyl)amino]
UNII
  • InChI=1S/C10H16N2O8/c13-7(14)3-5(9(17)18)11-1-2-12-6(10(19)20)4-8(15)16/h5-6,11-12H,1-4H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20) X mark.svgN
    Key: VKZRWSNIWNFCIQ-UHFFFAOYSA-N X mark.svgN
  • O=C(O)CC(NCCNC(CC(=O)O)C(=O)O)C(=O)O
Properties
C10H16N2O8
Molar mass 292.244 g·mol−1
Density 1.44 g mL−1
Melting point 220 to 222 °C (428 to 432 °F; 493 to 495 K)
Acidity (pKa)2.4
Basicity (pKb)11.6
Thermochemistry
−1.9541–−1.9463 MJ mol−1
−4.2755–−4.2677 MJ mol−1
Related compounds
Related alkanoic acids
 EDTA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethylenediamine-N,N'-disuccinic acid (EDDS) is an aminopolycarboxylic acid. It is a colourless solid that is used as chelating agent that may offer a biodegradable alternative to EDTA, which is currently used on a large scale in numerous applications.

Contents

Structure and properties

EDDS has two chiral centers, and as such three stereoisomers. [1] These are the enantiomeric (R,R) and (S,S) isomers and the achiral meso (R,S) isomer. As a biodegradable replacement for EDTA, only the (S,S) stereoisomer is of interest. The (R,S) and (R,R) stereoisomers are less biodegradable, whereas the (S,S) stereoisomer has been shown to be very effectively biodegraded even in highly polluted soils. [2]

Synthesis

EDDS was first synthesized from maleic acid and ethylenediamine. [3] [4] Some microorganisms have been manipulated for industrial-scale synthesis of (S,S)-EDDS from ethylenediamine and fumaric acid or maleic acid, which proceeds as follows: [5]

From aspartic acid

(S,S)-EDDS is produced stereospecifically by the alkylation of an ethylenedibromide with L-aspartic acid. Racemic EDDS is produced by the reaction of ethylenediamine with fumaric acid or maleic acid.

Coordination chemistry

An octahedral complex of EDDS. M(edds)revd.png
An octahedral complex of EDDS.

In comparing the effectiveness of (S,S)-EDDS versus EDTA as chelating agents for iron(III):

Formation ReactionFormation Constant
[Fe(H2O)6]3+ + (S,S)-EDDS4− → Fe[(S,S)-EDDS]− + 6 H2OKEDDS = 1020.6
[Fe(H2O)6]3+ + EDTA4− → Fe(EDTA)− + 6 H2OKEDTA = 1025.1

Because of the lower stability for [Fe(S,S)-EDDS]−, the useful range being roughly 3<pH (S,S)-EDDS<9 and 2<pHEDTA<11. However, this range is sufficient for most applications. [6]

Another comparison that can be made between (S,S)-EDDS and EDTA is the structure of the chelated complex. EDTA’s six donor sites form five five-membered chelate rings around the metal ion, four NC2OFe rings and one C2N2Fe ring. The C2N2Fe ring and two of NC2OFe rings define a plane, and two NC2OFe rings are perpendicular to the plane that contains the C2-symmetry axis. The five-membered rings are slightly strained. EDDS’s six donor sites form both five- and six-membered chelate rings around the metal ion: two NC2OFe rings, two NC3OFe rings, and one C2N2Fe ring. Studies of the crystal structure of the Fe[(S,S)-EDDS]− complex show that the two five-membered NC3OFe rings project out of the plane of the complex, reducing the equatorial ring strain that exists in the Fe[EDTA]− complex. [7] The complex also has C2 symmetry.

Uses

(S,S)-EDDS is a biodegradable chelating agent that offers an alternative to EDTA, of which 80 million kilograms are produced annually. Under natural conditions, EDTA has been found to convert to ethylenediaminetriacetic acid and then cyclize to the diketopiperazine, which accumulates in the environment as a persistent organic pollutant. [8] [9] (S,S)-EDDS was developed commercially as a biodegradable chelator and stabilizing agent in detergent and cosmetic formulations. [10] When EDDS is applied in chemical-enhanced soil remediation in excessive case (e.g., when applied for ex-situ soil washing), higher extraction efficiency for heavy metals can be achieved and the amount of extraction is less independent with the EDDS dosage; [11] On the other hand, during soil remediation which involves continuous flushing, metal extraction is often limited by the amount of EDDS. Under EDDS deficiency, initial unselective extraction of heavy metals was observed, followed by heavy metal exchange and re-adsorption of heavy metals that have lower stability constant with EDDS. [12]

Related Research Articles

<span class="mw-page-title-main">Iron deficiency (plant disorder)</span>

Iron (Fe) deficiency is a plant disorder also known as "lime-induced chlorosis". It can be confused with manganese deficiency. Soil iron concentration is high, but can become unavailable for absorption if soil pH is higher than 6.5. Excess of elements such as manganese in the soil can interfere with plant iron uptake triggering iron deficiency.

Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate 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, as in the case of zinc and its use as a maintenance therapy to prevent the absorption of copper in people with Wilson's disease.

<span class="mw-page-title-main">Ethylenediaminetetraacetic acid</span> Chemical compound

Ethylenediaminetetraacetic acid (EDTA), also called edetic acid after its own abbreviation, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. This white, water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH. It is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble. EDTA is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Nitrilotriacetic acid</span> Chemical compound

Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH2CO2H)3. It is a colourless solid that is used as a chelating agent, which forms coordination compounds with metal ions (chelates) such as Ca2+, Co2+, Cu2+, and Fe3+.

<span class="mw-page-title-main">Pentetic acid</span> DTPA: aminopolycarboxylic acid

Pentetic acid or diethylenetriaminepentaacetic acid (DTPA) is an aminopolycarboxylic acid consisting of a diethylenetriamine backbone with five carboxymethyl groups. The molecule can be viewed as an expanded version of EDTA and is used similarly. It is a white solid with limited solubility in water.

<span class="mw-page-title-main">Enterobactin</span> Chemical compound

Enterobactin is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.

<span class="mw-page-title-main">EDDHA</span> Chemical compound

EDDHA or ethylenediamine-N,N′-bis(2-hydroxyphenylacetic acid) is a chelating agent. Like EDTA, it binds metal ions as a hexadentate ligand, using two amines, two phenolate centers, and two carboxylates as the six binding sites. The complexes are typically anionic. The ligand itself is a white, water soluble powder. Both the free ligand and its tetraanionic chelating agent are abbreviated EDDHA. In contrast to EDDHA, most related aminopolycarboxylic acid chelating agents feature tertiary amines and few have phenolate groups.

In coordination chemistry, a stability constant is an equilibrium constant for the formation of a complex in solution. It is a measure of the strength of the interaction between the reagents that come together to form the complex. There are two main kinds of complex: compounds formed by the interaction of a metal ion with a ligand and supramolecular complexes, such as host–guest complexes and complexes of anions. The stability constant(s) provide(s) the information required to calculate the concentration(s) of the complex(es) in solution. There are many areas of application in chemistry, biology and medicine.

<span class="mw-page-title-main">Iminodiacetic acid</span> Chemical compound

Iminodiacetic acid is the organic compound with the formula HN(CH2CO2H)2, often abbreviated to IDA. A white solid, the compound is a dicarboxylic acid amine (the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). The iminodiacetate dianion is a tridentate ligand, forming metal complexes by forming two, fused, five membered chelate rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100. Complexes of IDA and EDTA were introduced in the early 1950's by Schwarzenbach.

The Hoagland solution is a hydroponic nutrient solution that was newly developed by Hoagland and Snyder in 1933, modified by Hoagland and Arnon in 1938, and revised by Arnon in 1950. It is one of the most popular artificial solution compositions for growing plants, in the scientific world at least, with more than 19,000 citations listed by Google Scholar. The Hoagland solution provides all essential elements for plant nutrition and is appropriate for supporting normal growth of a large variety of plant species.

<span class="mw-page-title-main">Cyclam</span> Chemical compound

Cyclam (1,4,8,11-tetraazacyclotetradecane) is an organic compound with the formula (NHCH2CH2NHCH2CH2CH2)2. Classified as an aza-crown ether, it is a white solid that is soluble in water. As a macrocyclic ligand, it binds strongly to many transition metal cations. The compound was first prepared by the reaction of 1,3-dibromopropane and ethylenediamine.

Rainer Schulin is a German zoologist, forest scientist and emeritus professor of soil protection at the ETH Zurich.

Parisa Mehrkhodavandi is a Canadian chemist and Professor of Chemistry at the University of British Columbia (UBC). Her research focuses on the design of new catalysts that can effect polymerization of sustainably sourced or biodegradable polymers.

<span class="mw-page-title-main">Ferric EDTA</span> Chemical compound

Ferric EDTA is the coordination complex formed from ferric ions and EDTA. EDTA has a high affinity for ferric ions. It gives yellowish aqueous solutions.

<span class="mw-page-title-main">Tetrasodium iminodisuccinate</span> Chemical compound

Tetrasodium iminodisuccinate is a sodium salt of iminodisuccinic acid, also referred to as N-(1,2-dicarboxyethyl)aspartic acid.

<i>N</i>-(2-Carboxyethyl)iminodiacetic acid Chemical compound

N-(2-Carboxyethyl)iminodiacetic acid or β-ADA(β-alanine diacetate) is a tetradentate complexing agent which forms stable 1:1 chelate complexes with cations having a charge number of at least +2, e.g. the "hard water forming" cations Ca2+ or Mg2+. N-(2-Carboxyethyl)iminodiacetic acid should not be confused with α-Alaninediacetic acid, also known as methylglycinediacetic acid (MGDA) or α-ADA. Alkaline earth and heavy metal complexes of both, α-ADA and β-ADA are biodegradable (in contrast to chelate complexes with conventional complexing agents such as EDTA).

Transition metal amino acid complexes are a large family of coordination complexes containing the conjugate bases of the amino acids, the 2-aminocarboxylates. Amino acids are prevalent in nature, and all of them function as ligands toward the transition metals. Not included in this article are complexes of the amides and ester derivatives of amino acids. Also excluded are the polyamino acids including the chelating agents EDTA and NTA.

Chelated platinum is an ionized form of platinum that forms two or more bonds with a counter ion. Some platinum chelates are claimed to have antimicrobial activity.

Cheluviation is the process in which the metal ions in the upper layer of the soil are combined with organic ligands to form coordination complexes or chelates, moving downwards through eluviation and then depositing.

References

  1. ↑ Neal, J. A.; Rose, N. J. (1968). "Stereospecific Ligands and Their Complexes. I. A Cobalt(III) Complex of Ethylenediaminedisuccinic Acid". Inorganic Chemistry. 7 (11): 2405–2412. doi:10.1021/ic50069a043.
  2. ↑ Tandy, S.; Ammann, A.; Schulin, R.; Nowack, B. (2006). "Biodegredation and speciation of residual SS-ethylenediaminedisuccinic acid (EDDS) in soil solution left after soil washing". Environmental Pollution. 142 (2): 191–199. doi:10.1016/j.envpol.2005.10.013. PMID   16338042.
  3. ↑ Barbier, M.; et al. (1963). "Synthese und Eigenschaften eines Analogen des Lycomarasmins und der Aspergillomarasmine". Liebigs Annalen. 668: 132–138. doi:10.1002/jlac.19636680115.
  4. ↑ USpatent 3158635,Kezerian, Charles; Ramsey, William M.,"Bisadducts of diamines and unsaturated acids",issued 1964-11-24
  5. ↑ Takahashi, R.; et al. (1999). "Production of (S,S)-Ethylenediamine-N,N'-disuccinic Acid from Ethylenediamine and Fumaric Acid by Bacteria". Biosci. Biotechnol. Biochem. 63 (7): 1269–1273. doi: 10.1271/bbb.63.1269 . PMID   27380235.
  6. ↑ Orama, M.; Hyvönen, H.; Saarinen, H.; Aksela, R. (2002). "Complexation of [S,S] and mixed stereoisomers of N,N'-ethylenediaminedisuccinic acid (EDDS) with Fe(III), Cu(II), Zn(II) and Mn(II) ions in aqueous solution". J. Chem. Soc., Dalton Trans. (24): 4644–4648. doi:10.1039/b207777a.
  7. ↑ Pavelčík, F; Majer, J. (1978). "The crystal and molecular structure of lithium [(S,S)-N,N'-ethylenediaminedisuccinato]cobaltate(III) trihydrate". Acta Crystallographica B. 34 (12): 3582–3585. doi:10.1107/S0567740878011644.
  8. ↑ Yuan, Z.; VanBriesen, J. M. (2006). "The Formation of Intermediates in EDTA and NTA Biodegradation". Environmental Engineering Science. 23 (3): 533–544. doi:10.1089/ees.2006.23.533.
  9. ↑ Yip, T.C.M.; Tsang, D.C.W.; Ng, K.T.W.; Lo, I.M.C. (2009). "Kinetic interactions of EDDS with soils. 1. Metal resorption and competition under EDDS deficiency". Environ. Sci. Technol. 43 (3): 831–836. Bibcode:2009EnST...43..831Y. doi:10.1021/es802030k. PMID   19245023.
  10. ↑ Schowanek, D.; Feijtel, T.C.J.; Perkins, C.M.; Hartman, F.A.; Federle, T.W.; Larson, R.J. (1997). "Biodegradation of (S,S), (R,R) and mixed stereoisomers of ethylene diamine disuccinic acid (EDDS), a transition metal chelator". Chemosphere. 34 (11): 2375–2391. doi:10.1016/S0045-6535(97)00082-9. PMID   9192467.
  11. ↑ Yip, T.C.M.; Tsang, D.C.W.; Ng, K.T.W.; Lo, I.M.C. (2009). "Empirical modeling of heavy metal extraction by EDDS from single-metal and multi-metal contaminated soils". Chemosphere. 74 (2): 301–307. Bibcode:2009Chmsp..74..301Y. doi:10.1016/j.chemosphere.2008.09.006. PMID   18851868.
  12. ↑ Tsang, D.C.W.; Yip, T.C.M.; Lo, I.M.C. (2009). "Kinetic interactions of EDDS with soils. 2. Metal-EDDS complexes in uncontaminated and metal-contaminated soils". Environ. Sci. Technol. 43 (3): 837–842. Bibcode:2009EnST...43..837T. doi:10.1021/es8020292. PMID   19245024.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.