Tetraacetylethylenediamine

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 {{convert|45|C|F}}. TAED and hydrogen peroxide react to form peroxyacetic acid, a more efficient bleach, allowing lower temperature wash cycles, around {{convert|40|C|F}}. TAED was first used in a commercial laundry detergent in 1978 (Skip by Unilever).{{cite book|author1=Smulders E.|author2=von Rybinski W.|author3=Sung E.|author4=Rähse W.|author5=Steber J.|author6=Wiebel F.|author7=Nordskog A.|title=Ullmann's Encyclopedia of Industrial Chemistry|date=2002|publisher=Wiley-VCH|chapter=Laundry Detergents}} Currently, TAED is the main bleach activator used in European laundry detergents and has an estimated annual consumption of 75 kt.{{cite book|author1=Reinhardt, G.|author2=Borchers, G.|editor1-last=Zoller|editor1-first=Uri|title=Handbook of Detergents Part E: Applications|date=2009|publisher=CRC Press|location=USA|isbn=9781574447576|chapter=Application of Bleaching Detergent Formulations}}

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):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}}.

TAED typically provides only two equivalents of peracetic acid, although four are theoretically possible.{{cite book|author1=Farr, J. P.|author2=Smith, W. L.|author3=Steichen,, D. S.|title=Kirk-Othmer Encyclopedia of Chemical Technology Vol. 4|date=1992|publisher=John Wiley & Sons, Inc.|pages=271–299|edition=4th|chapter=Bleaching Agents}}

Competing with perhydrolysis, TAED also undergoes some hydrolysis, which is an unproductive pathway.{{cite journal|last1=Hauthal, G. H., Schmidt, H., Scholz, J., Hofmann, J. and Pritzkow W.|title=Studies concerning the mechanism of bleach activation|journal=Tenside Surf. Det.|date=1990|volume=27|issue=3|doi=10.1515/tsd-1990-270314 |s2cid=235325458 }}{{cite journal|last1=Hofmann, J., Just, G., Pritzkow, W. and Schmidt, H.|title=Bleaching activators and the mechanism of bleaching activation|journal=Journal für Praktische Chemie/Chemiker-Zeitung|date=1992|volume=334|issue=4|pages=293–297|doi=10.1002/prac.19923340402}}

TAED is prepared in a two-stage process from ethylenediamine and acetic anhydride. The process is nearly quantitative.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 1979Europäische 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 1982Europäisches 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

Powdered TAED is stabilized by granulation with the aid of the sodium salt of carboxymethylcellulose (Na-CMC),US-Patent US 5,100,576, [https://patents.google.com/patent/US5100576 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. 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.Clariant Surfactant Division: [http://www.detergents-intermediates.clariant.com/C12575E4001FB2B8/vwLookupDownloads/DetergentsIntermediates_Newsroom_Brochures_Peractive.pdf/$FILE/DetergentsIntermediates_Newsroom_Brochures_Peractive.pdf The Clean and Clever Way of Bleaching - PERACTIVE] {{Webarchive|url=https://web.archive.org/web/20130717231307/http://www.detergents-intermediates.clariant.com/C12575E4001FB2B8/vwLookupDownloads/DetergentsIntermediates_Newsroom_Brochures_Peractive.pdf/$FILE/DetergentsIntermediates_Newsroom_Brochures_Peractive.pdf |date=2013-07-17 }} (PDF; 865 kB), 08.99

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.HERA Human & Environmental Risk Assessment on ingredients of European household cleaning products: [http://www.heraproject.com/files/2-F-04-HERA%20TAED%20full%20web%20wd.pdf Tetraacetylethylenediamine (TAED), CAS 10543-57-4] (PDF; 666 kB), Draft, DECEMBER 2002. TAED, TriAED and DAED are all completely biodegradable and substantially removed during wastewater treatment.{{cite book|author1=Gilbert, P. A.|editor1-last=de Oude|editor1-first=N. T.|title=The Handbook of Environmental Chemistry, Vol. 3 Part F Antropogenic Compounds: Detergents|date=1992|publisher=Springer-Verlag|location=Berlin|isbn=354053797X|chapter=TAED-Tetraacetylethylenediamine}}

• [https://web.archive.org/web/20070311010319/http://www.patentstorm.us/patents/6528470.html US Patent 6528470 - Bleaching activator]
• [http://www.heraproject.com/RiskAssessment.cfm?SUBID=2 HERA RiskAssessment]

Category:Cleaning product components

Category:Acetamides