Tetraacetylethylenediamine

Tetraacetylethylenediamine

Names
IUPAC name Tetraacetylethylenediamine
Other names TAED, N,N'-ethylenebis(diacetamide)
Identifiers
CAS Number	10543-57-4 N
3D model (Jmol)	Interactive image
ChemSpider	59725 N
ECHA InfoCard	100.031.009
PubChem	66347
UNII	P411ED0N2B N
InChI InChI=1S/C10H16N2O4/c1-7(13)11(8(2)14)5-6-12(9(3)15)10(4)16/h5-6H2,1-4H3 N Key: BGRWYDHXPHLNKA-UHFFFAOYSA-N N 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
SMILES O=C(C)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O
Properties
Chemical formula	C10H16N2O4
Molar mass	228.25 g·mol−1
Appearance	Colorless solid
Density	0.9
Melting point	149 to 154 °C (300 to 309 °F; 422 to 427 K)
Solubility in water	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).
N  (what is YN ?)
Infobox references

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.

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. Hydrogen peroxide is however an inefficient bleach below 60 °C (140 °F). TAED and hydrogen peroxide 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). Currently, TAED is the main bleach activator used in European laundry detergents and has an estimated annual consumption of 75 kt.

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):

TAED typically provides only two equivalents of peracetic acid, although four are theoretically possible. Competing with perhydrolysis, TAED also undergoes some hydrolysis, which is an unproductive pathway. and 1.7 mol.

TAED is prepared in a two-stages from ethylenediamine and acetic anhydride. The process is nearly quantitative.