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Trisodium ethylenediamine disuccinate
"Descrizione"
by Frank123 (12008 pt)
2023-Jul-22 18:33

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Trisodium ethylenediamine disuccinate EDDS is a chemical compound, trisodium salt of disuccinic acid, using Ethylenediamine as its building block.

The name describes the structure of the molecule:

  • Trisodium indicates the presence of three sodium ions in the molecule.
  • Ethylenediamine refers to an organic structure that contains two amine groups (-NH₂) separated by an ethylene group (-CH₂CH₂-).
  • Disuccinate indicates that there are two units of succinic acid attached to the ethylenediamine molecule.

Description of the raw materials used in its production:

  • Ethylenediamine  is a diamine with the chemical formula H2NCH2CH2NH2. It is often produced synthetically through ammonolysis or hydrolysis of ethylenediammonium.
  • Succinic Acid  is a dicarboxylic acid with the chemical formula HOOC(CH2)2COOH. It can be derived from natural sources such as certain plants or synthesized through the hydrogenation of maleic acid.
  • Sodium  is an alkali metal commonly used to prepare salts like Trisodium Ethylenediamine Disuccinate.

Industrial chemical synthesis step-by-step:

  • Condensation of Ethylenediamine with Succinic Acid - Ethylenediamine reacts with succinic acid in a condensation reaction to form Ethylenebis(imino)disuccinic acid (EDDS). This reaction involves the elimination of water.
  • Neutralization with Sodium - The obtained EDDS is neutralized with sodium to form Trisodium Ethylenediamine Disuccinate. During this neutralization, the EDDS acquires three sodium ions (Na+) to form the final compound.
  • Purification - Trisodium Ethylenediamine Disuccinate is then purified to remove any impurities and by-products.
  • Drying and Packaging - The purified product is dried to remove residual moisture and then packaged for distribution and use in the detergent and cleaning product industry.

It appears as a white crystalline powder.

Cosmetics

It has chelating function predominantly used in shampoos.

  • Chelating agent. It has the function of preventing unstable reactions and improving the bioavailability of chemical components within a product, and removes calcium and magnesium cations that can cause cloudiness in clear liquids.

Other uses

Trisodium ethylenediamine disuccinate [S,S]-ethylenediamine-disuccinate can be used as a biodegradable chelator for the remediation of metal pollution by soil washing because although it has two chiral carbons and three stereoisomers, one of these, [S,S] is readily biodegradable (1).

The most relevant studies on this chemical compound have been selected with a summary of their contents:

Trisodium ethylenediamine disuccinate studies

Typical commercial product characteristics  Ethylene diamino-disuccinic acid

AppearanceWhite powder
Boiling Point
516.7±50.0°C at 760 mmHg
Melting Point
220-222ºC
Flash Point266.3±30.1°C
Density1.5±0.1 g/cm3
Loss on drying
≤16.0%
Assay≥98.0%
Shelf life
24 Months
PSA212.56000
LogP-0.14
Vapor Pressure
0.0±2.9 mmHg at 25°C
Index of Refraction
1.562


  • Molecular Formula  C10H16N2O8      C10H13N2Na3O8
  • Molecular Weight    292.24
  • CAS  20846-91-7    178949-82-1
  • UNII    5WK2FGJ113
  • EC Number   202-045-3
  • DSSTox Substance ID  DTXSID1051852
  • IUPAC  (2S)-2-[2-[[(1S)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid
  • 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)/t5-,6-/m0/s1 
  • InChl Key      VKZRWSNIWNFCIQ-WDSKDSINSA-N
  • SMILES   C(CNC(CC(=O)O)C(=O)O)NC(CC(=O)O)C(=O)O
  • MDL number  
  • PubChem Substance ID    
  • RTECS   CI9450800

Synonyms

  • N,N'-Ethylenedi-L-aspartic acid
  • L-Aspartic acid, N,N-1,2-ethanediylbis-
  • Ethylene diamino-disuccinic acid
  • Ethylendiamine-N,N-disuccinic acid
  • (2S)-2-[2-[[(1S)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid
  • N,N′-Ethylenedi-(aspartic acid) trisodium salt
  • Trisodium ethylenediamine-N,N′-disuccinate
  • Ethylenediamine-N,N′-disuccinic acid trisodium salt

References_______________________________________________________________________

(1) Boethling, R.S., Sommer, E. and DiFiore, D., 2007. Designing small molecules for biodegradability. Chemical reviews, 107(6), pp.2207-2227.

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