Tetrasodium iminodisuccinate
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
Tetrasodium N-(1,2-dicarboxylatoethyl)-ξ-aspartate(2−) | |
| Systematic IUPAC name
Tetrasodium 2,2′-azanediyldibutanedioate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.117.797 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H7NNa4O8 | |
| Molar mass | 337.102 g·mol−1 |
| Appearance | colorless crystals[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrasodium iminodisuccinate is a sodium salt of iminodisuccinic acid, also referred to as N-(1,2-dicarboxyethyl)aspartic acid.[2]
Iminodisuccinic acid can be prepared by reacting maleic anhydride with ammonia and sodium hydroxide:[3]
For the synthesis of tetrasodium iminodisuccinate, maleic anhydride is reacted with sodium hydroxide in water at elevated temperature. A concentrated disodium maleate solution is formed to which ammonia is added[4] at 90 to 145 °C, then excess water and ammonia is distilled off. An aqueous solution containing about 34% tetrasodium iminodisuccinate is obtained with yields of up to 98%.[5] Spray-drying can be used to obtain a mixture of solids consisting of> 65% tetrasodium iminodisuccinate salts (essentially the tetra sodium salts), <2% maleic acid sodium salts, <8% fumaric acid sodium salts, <2% malic acid sodium salts, <15% aspartic acid sodium salts, and >15% water. The by-products of the reaction do not affect the complexing capacity or biodegradability of the tetrasodium iminodisuccinate.
| Product | IDS-Na4 salt | Na2 fumarate | Na2 aspartate | Na2 malate | Na2 maleate | water |
|---|---|---|---|---|---|---|
| Industrial cleaner[6] | 72,1 | 5,6 | 10,6 | - | - | 8,9 |
| Baypure CX 100/34 %[5] | > 33,0 | < 2,5 | < 7,0 | < 0,5 | < 0,3 | < 59,0 |
| Baypure CX 100 solid[5] | > 65,0 | < 8,0 | < 15,0 | < 2,0 | < 2,0 | < 15,0 |
| Baypure CX 100 solid G[5] | > 78,0 | < 5,0 | < 15,0 | < 0,7 | < 0,5 | < 4,0 |
Properties
As a commercial product, tetrasodium iminodisuccinate is sold either as a white powder (solid mixture, produced by spray drying of the aqueous solution, Baypure® CX 100) or as granular material with a content of> 78% tetrasodium iminodisuccinate.
Tetrasodium iminodisuccinate is a chelating agent, forming complexes of moderate stability (10−16), which includes (as a pentadentate ligand) alkaline earth and polyvalent heavy metal ions with one molecule of water in an octahedral structure.[7] In 0.25% aqueous solution, a pH of 11.5 results for tetrasodium iminodisuccinate. The salt is stable for several hours in weakly acidic solution (pH> 4-7) even at 100 °C and for weeks in strongly alkaline solutions even at an elevated temperature (50 °C).
Tetrasodium iminodisuccinate is classified as readily biodegradable according to OECD methods (OECD 302 B, 100% after 28 days and OECD 301 E, 78% after 28 days).[5] As biodegradable alternatives from the class of widespread chelating agents, only nitrilotriacetic acid (NTA) is sufficiently biodegradable under certain conditions (which is suspected of being carcinogenic, though) and the chelating active amino acid derivatives β-alaninediacetic acid and methylglycine diacetic acid (Trilon M®).