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, than 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.
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®).
Use
Iminodisuccinic acid has been distributed by Lanxess since 1998 under the trade name Baypure CX 100 as complexing agent.[3] It reacts with the calcium and magnesium ions in water and forms chelate complexes of medium stability.[5] This complexation prevents the formation of insoluble salts (deposits) and soaps (lime soaps) and thus improves the effect of detergents and dishwashing detergents, hand soaps and shampoos. As a result, the amount of conventional builders in solid detergents (carbonates, silicates, phosphates, citrates, zeolites) can be reduced or fully replaced. The calcium binding capacity for tetrasodium iminodisuccinate is approximately 230 mg CaCO3/g salt and therefore lies between the capacity of DTPA Na5 salt (210 mg CaCO3 Na salt) and EDTA Na4 salt (280 mg CaCO3/g Na-Salz).
Also most other applications of tetrasodium iminodisuccinate Na salt are based on the complexation of alkaline earth and heavy metal ions e. g. in industrial cleaners for the removal of biofilms and limescale, cosmetics, in electroplating, in construction (retardation), textile (protection against graying) and paper. When tetrasodium iminodisuccinate is used in solid detergent formulations instead of the common phosphonates, it inhibits the heavy metal ion catalyzed decomposition of hydrogen peroxide in bleach-containing wash liquors.
Complexes of tetrasodium iminodisuccinate with Fe3+, Cu2+, Zn2+ and Mn2+ ions are used as micronutrients, as they are providing important trace elements for plants in readily absorbable form; both granulated as soil fertilizer and dissolved as foliar spray. The so far commonly in plant protection applied complexing agents such as EDTA, DTPA (diethylenetriamine pentaacetic acid), EDDHA (ethylenediamine dihydroxyphenylacetic acid) or HBED (N,N'-di(2-hydroxybenzyl)ethylenediamine-N, N'-diacetic acid) are difficult to virtually non-biodegradable. In contrast, IDHA trace element complexes offer an interesting alternative.[7]
Stereoisomerism
The preparation from the achiral starting materials provides a mixture of three epimers:[8] (R,R)-iminodisuccinate, (R,S)-iminodisuccinate, and (S,S)-iminodisuccinate. The two meso compounds [R,S] and [S,R] are identical. The enzymatic degradation in the first two cases produces the compounds D-aspartic acid and fumaric acid, and in the third case produces L-aspartic acid and fumaric acid, which are metabolized further.
^ abDorota Kołodyńska (2011), Robert Y. Ning (ed.), "Chelating Agents of a New Generation as an Alternative to Conventional Chelators for Heavy Metal Ions Removal from Different Waste Waters", Expanding Issues in Desalination, Hier: S. 344 (in German), InTech, pp. 339–370, doi:10.5772/21180, ISBN978-953-307-624-9
^US 6107518, Torsten Groth, Winfried Joentgen, Paul Wagner, Frank Dobert, Eckhard Wenderoth, Thomas Roick, "Preparation and use of iminodisuccinic acid salts", issued 2000-08-22, assigned to Bayer AG
^ abcdefLanxess AG, General Product Information: Baypure
^nicnas.gov.au: Aspartic acid, N-(1,2-dicarboxyethyl)-, tetrasodium salt 2014-02-12 at the Wayback Machine, August 2002.
^E. Sanchez et al.: Iminodisuccinate Pathway Map, Manchester College, April 17, 2013
January 23, 2023
tetrasodium, iminodisuccinate, tetrasodiumiminodisuccinate, sodium, salt, iminodisuccinic, acid, also, referred, dicarboxyethyl, aspartic, acid, namespreferred, iupac, name, tetrasodium, azanediyldibutanedioateidentifierscas, number, 144538, model, jsmol, inte. Tetrasodiumiminodisuccinate is a sodium salt of iminodisuccinic acid also referred to as N 1 2 dicarboxyethyl aspartic acid 2 Tetrasodium iminodisuccinate NamesPreferred IUPAC name Tetrasodium 2 2 azanediyldibutanedioateIdentifiersCAS Number 144538 83 0 Y3D model JSmol Interactive imageECHA InfoCard 100 117 797EC Number 604 420 0PubChem CID 9927753UNII GYS41J2635 YCompTox Dashboard EPA DTXSID1051723InChI InChI 1S C8H11NO8 4Na c10 5 11 1 3 7 14 15 9 4 8 16 17 2 6 12 13 h3 4 9H 1 2H2 H 10 11 H 12 13 H 14 15 H 16 17 q 4 1 p 4Key GYBINGQBXROMRS UHFFFAOYSA JSMILES C C C O O NC CC O O C O O C O O Na Na Na Na PropertiesChemical formula C 8H 7N Na 4O 8Molar mass 337 102 g mol 1Appearance colorless crystals 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Preparation 2 Properties 3 Use 4 Stereoisomerism 5 ReferencesPreparation EditIminodisuccinic 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 than 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 gt 65 tetrasodium iminodisuccinate salts essentially the tetra sodium salts lt 2 maleic acid sodium salts lt 8 fumaric acid sodium salts lt 2 malic acid sodium salts lt 15 aspartic acid sodium salts and gt 15 water The by products of the reaction do not affect the complexing capacity or biodegradability of the tetrasodium iminodisuccinate Composition of commercial products in by weight Product IDS Na4 salt Na2 fumarate Na2 aspartate Na2 malate Na2 maleate waterIndustrial cleaner 6 72 1 5 6 10 6 8 9Baypure CX 100 34 5 gt 33 0 lt 2 5 lt 7 0 lt 0 5 lt 0 3 lt 59 0Baypure CX 100 solid 5 gt 65 0 lt 8 0 lt 15 0 lt 2 0 lt 2 0 lt 15 0Baypure CX 100 solid G 5 gt 78 0 lt 5 0 lt 15 0 lt 0 7 lt 0 5 lt 4 0Properties EditAs 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 gt 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 gt 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 b alaninediacetic acid and methylglycine diacetic acid Trilon M Use EditIminodisuccinic acid has been distributed by Lanxess since 1998 under the trade name Baypure CX 100 as complexing agent 3 It reacts with the calcium and magnesium ions in water and forms chelate complexes of medium stability 5 This complexation prevents the formation of insoluble salts deposits and soaps lime soaps and thus improves the effect of detergents and dishwashing detergents hand soaps and shampoos As a result the amount of conventional builders in solid detergents carbonates silicates phosphates citrates zeolites can be reduced or fully replaced The calcium binding capacity for tetrasodium iminodisuccinate is approximately 230 mg CaCO3 g salt and therefore lies between the capacity of DTPA Na5 salt 210 mg CaCO3 Na salt and EDTA Na4 salt 280 mg CaCO3 g Na Salz Also most other applications of tetrasodium iminodisuccinate Na salt are based on the complexation of alkaline earth and heavy metal ions e g in industrial cleaners for the removal of biofilms and limescale cosmetics in electroplating in construction retardation textile protection against graying and paper When tetrasodium iminodisuccinate is used in solid detergent formulations instead of the common phosphonates it inhibits the heavy metal ion catalyzed decomposition of hydrogen peroxide in bleach containing wash liquors Complexes of tetrasodium iminodisuccinate with Fe3 Cu2 Zn2 and Mn2 ions are used as micronutrients as they are providing important trace elements for plants in readily absorbable form both granulated as soil fertilizer and dissolved as foliar spray The so far commonly in plant protection applied complexing agents such as EDTA DTPA diethylenetriamine pentaacetic acid EDDHA ethylenediamine dihydroxyphenylacetic acid or HBED N N di 2 hydroxybenzyl ethylenediamine N N diacetic acid are difficult to virtually non biodegradable In contrast IDHA trace element complexes offer an interesting alternative 7 Stereoisomerism EditThe preparation from the achiral starting materials provides a mixture of three epimers 8 R R iminodisuccinate R S iminodisuccinate and S S iminodisuccinate The two meso compounds R S and S R are identical The enzymatic degradation in the first two cases produces the compounds D aspartic acid and fumaric acid and in the third case produces L aspartic acid and fumaric acid which are metabolized further References Edit Nu Calgon Safety data sheet dead link Van Iperen International IDHA chelates a b Dorota Kolodynska 2011 Robert Y Ning ed Chelating Agents of a New Generation as an Alternative to Conventional Chelators for Heavy Metal Ions Removal from Different Waste Waters Expanding Issues in Desalination Hier S 344 in German InTech pp 339 370 doi 10 5772 21180 ISBN 978 953 307 624 9 US 6107518 Torsten Groth Winfried Joentgen Paul Wagner Frank Dobert Eckhard Wenderoth Thomas Roick Preparation and use of iminodisuccinic acid salts issued 2000 08 22 assigned to Bayer AG a b c d e f Lanxess AG General Product Information Baypure nicnas gov au Aspartic acid N 1 2 dicarboxyethyl tetrasodium salt Archived 2014 02 12 at the Wayback Machine August 2002 a b ADOB Biodegradable chelates E Sanchez et al Iminodisuccinate Pathway Map Manchester College April 17 2013 Retrieved from https en wikipedia org w index php title Tetrasodium iminodisuccinate amp oldid 1052553402, wikipedia, wiki, book, books, library,
