EDDS

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This article is about the chemical. For the ICAO code EDDS, see Stuttgart Airport.
EDDS
Skeletal formula of EDDS
Names
IUPAC name
Ethylenediamine-N,N′-disuccinic acid[citation needed]
Identifiers
20846-91-7 YesY
ChemSpider 109992 N
9489961 2-[(2-{[(1S)-1-Carboxyethyl]amino}ethyl)amino] N
8283888 (2R)-2-[(2-{[(1R)-1-Carboxyethyl]amino}ethyl)amino] N
435376 (2S)-2-[(2-{[(1S)-1-Carboxyethyl]amino}ethyl)amino] N
Jmol 3D model Interactive image
Interactive image
MeSH N,N'-ethylenediamine+disuccinic+acid
PubChem 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]
  • 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) N
    Key: VKZRWSNIWNFCIQ-UHFFFAOYSA-N N
  • [o]:c(:[oH])CC(NCCNC(Cc(:[o]):[oH])c(:[o]):[oH])c(:[o]):[oH]
  • OC(=O)CC(NCCNC(CC(O)=O)C(O)=O)C(O)=O
Properties
C10H16N2O8
Molar mass 292.24 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).
N verify (what is YesYN ?)
Infobox references

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.

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

In its octahedral complexes, edds poses the six-membered chelate rings in the equatorial positions.

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

Formation Reaction Formation Constant
[Fe(H2O)6]3+ + (S,S)-EDDS4− → Fe[(S,S)-EDDS]− + 6 H2O KEDDS = 1020.6
[Fe(H2O)6]3+ + EDTA4− → Fe(EDTA)− + 6 H2O KEDTA = 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] 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;[10] 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.[11]

External links

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ US patent 3158635, Kezerian, Charles; Ramsey, William M., "Bisadducts of diamines and unsaturated acids", issued 1964-11-24 
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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