Tetraacetylethylenediamine

Tetraacetylethylenediamine
IUPAC name Tetraacetylethylenediamine
Other names TAED, N,N'-ethylenebis(diacetamide)
Identifiers
CAS number	10543-57-4
ChemSpider	10629141 Y
Jmol-3D images	Image 1
SMILES O=C(C)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O
InChI InChI=1S/C10H16N2O4/c1-5(13)9(11,6(2)14)10(12,7(3)15)8(4)16/h11-12H2,1-4H3 Y Key: FRPJTGXMTIIFIT-UHFFFAOYSA-N Y InChI=1/C10H16N2O4/c1-5(13)9(11,6(2)14)10(12,7(3)15)8(4)16/h11-12H2,1-4H3 Key: FRPJTGXMTIIFIT-UHFFFAOYAA
Properties
Molecular formula	C10H16N2O4
Molar mass	228.25
Appearance	colourless solid
Density	0.9
Melting point	149-154 °C, 268 K, -96 °F
Solubility in water	0.2 g/L @ 20ºC
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tetraacetylethylenediamine, commonly abbreviated TAED, is an organic compound with the formula (CH₃C(O))₂NCH₂CH₂N(C(O)CH₃)₂. Used as peroxide bleach activator for household detergents and for paper pulp. It is produced by acetylation of ethylenediamine.

Use in laundry detergents and mechanism of action

TAED is an important component of detergents and bleaches. Its is an activator for "active oxygen" bleaching agents. Such active oxygen bleaching agents release hydrogen peroxide during the wash cycle. Such agents include sodium perborate, sodium percarbonate, sodium perphosphate, sodium persulfate, and urea peroxide. The released hydrogen peroxide is an inefficient bleach below 40 °C, except in the presence of activators such as TAED.

The activation process entails a reaction of the hydrogen peroxide with TAED to release peracetic acid, which is a fast-acting bleaching agent.:^[1]

(CH₃C(O))₂NCH₂CH₂N(C(O)CH₃)₂ + H₂O₂ → (CH₃C(O))₂NCH₂CH₂NH(C(O)CH₃) + CH₃CO₃H

References

1. ^ 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.

See also

• US Patent 6528470 - Bleaching activator
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