Tetraacetylethylenediamine

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Tetraacetylethylenediamine
Tetraacetylethylenediamine.svg
Tetraacetylethylenediamine Ball and Stick.png
Names
Preferred IUPAC name
N,N′-(Ethane-1,2-diyl)bis(N-acetylacetamide)
Other names
TAED, N,N′-ethylenebis(diacetamide)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.031.009 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H16N2O4/c1-7(13)11(8(2)14)5-6-12(9(3)15)10(4)16/h5-6H2,1-4H3 X mark.svgN
    Key: BGRWYDHXPHLNKA-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C10H16N2O4/c1-7(13)11(8(2)14)5-6-12(9(3)15)10(4)16/h5-6H2,1-4H3
    Key: BGRWYDHXPHLNKA-UHFFFAOYAK
  • O=C(C)N(C(C)=O)CCN(C(C)=O)C(C)=O
Properties
C10H16N2O4
Molar mass 228.248 g·mol−1
AppearanceColorless solid
Density 0.9
Melting point 149 to 154 °C (300 to 309 °F; 422 to 427 K)
0.2 g/L @ 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetraacetylethylenediamine, commonly abbreviated as TAED, is an organic compound with the formula (CH3C(O))2NCH2CH2N(C(O)CH3)2. This white solid is commonly used as a bleach activator in laundry detergents and for paper pulp. It is produced by acetylation of ethylenediamine.

Contents

Use and mechanism of action

TAED is an important component of laundry detergents that use "active oxygen" bleaching agents. Active oxygen bleaching agents include sodium perborate, sodium percarbonate, sodium perphosphate, sodium persulfate, and urea peroxide. These compounds release hydrogen peroxide during the wash cycle, but the release of hydrogen peroxide is low when these compounds are used in temperatures below 45 °C (113 °F). TAED and hydrogen peroxide react to form peroxyacetic acid, a more efficient bleach, allowing lower temperature wash cycles, around 40 °C (104 °F). TAED was first used in a commercial laundry detergent in 1978 (Skip by Unilever). [1] Currently, TAED is the main bleach activator used in European laundry detergents and has an estimated annual consumption of 75 kt. [2]

Perhydrolysis

TAED reacts with alkaline peroxide via the process called perhydrolysis releasing of peracetic acid. The first perhydrolysis gives triacetylethylenediamine (TriAED) and the second gives diacetylethylenediamine (DAED): [3]

Peracetic acid production from the hydrogen peroxide and TAED.svg

TAED typically provides only two equivalents of peracetic acid, although four are theoretically possible. [4] Competing with perhydrolysis, TAED also undergoes some hydrolysis, which is an unproductive pathway. [5] [6]

Preparation

TAED is prepared in a two-stage process from ethylenediamine and acetic anhydride. The process is nearly quantitative. [7] [8] [9]

TAED 2-step-synthesis.svg

Properties

Powdered TAED is stabilized by granulation with the aid of the sodium salt of carboxymethylcellulose (Na-CMC), [10] which are sometimes additionally coated blue or green. Despite the relatively low solubility of TAED in cool water, (1 g/L at 20 °C), the granulate dissolves rapidly in the washing liquor.

The peroxyacetic acid formed has bactericidal, virucidal and fungicidal properties, thereby enabling TAED with percarbonate to disinfect and deodorize. [11]

Ecology

Triacetylethylenediamine is mostly non-toxic and easily biodegradable. TAED and its byproduct DAED have low aquatic ecotoxicity. Triacetylethylenediamine shows a very low toxicity in all exposure routes, is practically non-irritating effect on skin and eye, and does not give any indication of skin sensitization. It is not mutagenic and not teratogenic. [12] TAED, TriAED and DAED are all completely biodegradable and substantially removed during wastewater treatment. [13]

Related Research Articles

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

Sodium percarbonate, or sodium carbonate peroxide is a chemical substance with formula Na
2H
3CO
6. It is an adduct of sodium carbonate and hydrogen peroxide whose formula is more properly written as 2 Na
2CO
3 · 3 H
2O
2. It is a colorless, crystalline, hygroscopic and water-soluble solid. It is sometimes abbreviated as SPC. It contains 32.5% by weight of hydrogen peroxide.

<span class="mw-page-title-main">Hydrogen peroxide–urea</span> Chemical compound

Hydrogen peroxide–urea is a white crystalline solid chemical compound composed of equal amounts of hydrogen peroxide and urea. It contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in dentistry, it is used as a source of hydrogen peroxide when dissolved in water for bleaching, disinfection and oxidation.

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Sodium perborate is chemical compound whose chemical formula may be written NaH2BO4, Na2H4B2O8, or, more properly, [Na+]2[B2O4(OH)4]2−. Its name is sometimes abbreviated as PBS.

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Peracetic acid (also known as peroxyacetic acid, or PAA) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive.

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

Sodium persulfate is the inorganic compound with the formula Na2S2O8. It is the sodium salt of peroxydisulfuric acid, H2S2O8, an oxidizing agent. It is a white solid that dissolves in water. It is almost non-hygroscopic and has good shelf-life.

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Pyridine-<i>N</i>-oxide Chemical compound

Pyridine-N-oxide is the heterocyclic compound with the formula C5H5NO. This colourless, hygroscopic solid is the product of the oxidation of pyridine. It was originally prepared using peroxyacids as the oxidising agent. The compound is used infrequently as an oxidizing reagent in organic synthesis.

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

Tetraethoxymethane is a chemical compound which is formally formed by complete ethylation of the hypothetical orthocarbonic acid C(OH)4 (orthocarbonic acid violates the Erlenmeyer rule and is unstable in free state).

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

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References

  1. ↑ Smulders E.; von Rybinski W.; Sung E.; Rähse W.; Steber J.; Wiebel F.; Nordskog A. (2002). "Laundry Detergents". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH.
  2. ↑ Reinhardt, G.; Borchers, G. (2009). "Application of Bleaching Detergent Formulations". In Zoller, Uri (ed.). Handbook of Detergents Part E: Applications. USA: CRC Press. ISBN   9781574447576.
  3. ↑ D. Martin Davies and Michael E. Deary "Kinetics of the hydrolysis and perhydrolysis of tetraacetylethylenediamine, a peroxide bleach activator" J. Chem. Soc., Perkin Trans. 2, 1991, pages 1549 - 1552. doi : 10.1039/P29910001549.
  4. ↑ Farr, J. P.; Smith, W. L.; Steichen,, D. S. (1992). "Bleaching Agents". Kirk-Othmer Encyclopedia of Chemical Technology Vol. 4 (4th ed.). John Wiley & Sons, Inc. pp. 271–299.{{cite book}}: CS1 maint: multiple names: authors list (link)
  5. ↑ Hauthal, G. H., Schmidt, H., Scholz, J., Hofmann, J. and Pritzkow W. (1990). "Studies concerning the mechanism of bleach activation". Tenside Surf. Det. 27 (3). doi:10.1515/tsd-1990-270314. S2CID   235325458.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ↑ Hofmann, J., Just, G., Pritzkow, W. and Schmidt, H. (1992). "Bleaching activators and the mechanism of bleaching activation". Journal für Praktische Chemie/Chemiker-Zeitung. 334 (4): 293–297. doi:10.1002/prac.19923340402.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ↑ Europäische Patentanmeldung EPA 004 919, Verfahren zur Herstellung von N,N,N’,N’-Tetraacetyl-ethylendiamin, Erfinder: G. Müller-Schiedmayer, R. Aigner, Anmelder: Hoechst AG, veröffentlicht am 31. Oktober 1979
  8. ↑ Europäische Patentanmeldung EPA 0 051 739 A1, Verfahren zur Herstellung von N,N,N’,N’-Tetraacetylethylendiamin, Erfinder: W. Köhler et al., Anmelder: BASF AG, veröffentlicht am 19. Mai 1982
  9. ↑ Europäisches Patent EP 0 238 958 B1, Verfahren zur Reinigung von Tetraacetylethylendiamin, Erfinder: K. Köster, F.-J. Carduck, Anmelder: Henkel KG aA, veröffentlicht am 12. Juni 1991
  10. ↑ US-Patent US 5,100,576, Process for the preparation of a readily soluble bleach activator granulate with a long shelf life, Erfinder: J. Cramer et al., Anmelder: Hoechst AG, erteilt am 31. März 1992.
  11. ↑ Clariant Surfactant Division: The Clean and Clever Way of Bleaching - PERACTIVE Archived 2013-07-17 at the Wayback Machine (PDF; 865 kB), 08.99
  12. ↑ HERA Human & Environmental Risk Assessment on ingredients of European household cleaning products: Tetraacetylethylenediamine (TAED), CAS 10543-57-4 (PDF; 666 kB), Draft, DECEMBER 2002.
  13. ↑ Gilbert, P. A. (1992). "TAED-Tetraacetylethylenediamine". In de Oude, N. T. (ed.). The Handbook of Environmental Chemistry, Vol. 3 Part F Antropogenic Compounds: Detergents. Berlin: Springer-Verlag. ISBN   354053797X.
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