Tetraacetylethylenediamine, commonly abbreviated as TAED, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

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.

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 perborate is chemical compound whose chemical formula may be written , , or, more properly, ·. Its name is sometimes abbreviated as PBS (not to be confused with phosphate-buffered saline). The compound is commonly encountered in anhydr ...

sodium percarbonate Sodium percarbonate is a chemical substance with formula . It is an adduct of sodium carbonate ("soda ash" or "washing soda") and hydrogen peroxide (that is, a perhydrate) whose formula is more properly written as 2 · 3 . ...

, sodium perphosphate,

sodium persulfate Sodium persulfate is the inorganic compound with the formula Sodium, Na2Sulfur, S2Oxygen, O8. 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 an ...

, and urea peroxide. These compounds release

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%� ...

during the wash cycle, but the release of

is low when these compounds used in temperatures below . TAED and

react to form

peroxyacetic acid 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. Peracetic ac ...

, a more efficient bleach, allowing lower temperature wash cycles, around . TAED was first used in a commercial laundry detergent in 1978 (

Skip Skip or Skips may refer to: Acronyms * SKIP (Skeletal muscle and kidney enriched inositol phosphatase), a human gene * Simple Key-Management for Internet Protocol * SKIP of New York (Sick Kids need Involved People), a non-profit agency aidi ...

Unilever Unilever plc is a British multinational consumer goods company with headquarters in London, England. Unilever products include food, condiments, bottled water, baby food, soft drink, ice cream, instant coffee, cleaning agents, energy dri ...

). Currently, TAED is the main bleach activator used in European laundry detergents and has an estimated annual consumption of 75 kt.

Perhydrolysis

TAED reacts with alkaline peroxide via the process called perhydrolysis releasing of

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

. 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 Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...

, which is an unproductive pathway.

Preparation

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 1979 The acetic acid by-product is recycled as acetic anhydride.

Properties

Powdered TAED is stabilized by

granulation Granulation is the process of forming grains or granules from a powdery or solid substance, producing a granular material. It is applied in several technological processes in the chemical and pharmaceutical industries. Typically, granulation invo ...

with the aid of the sodium salt of

carboxymethylcellulose Carboxymethyl cellulose (CMC) or cellulose gum is a cellulose derivative with carboxymethyl groups (-CH2-COOH) bound to some of the hydroxyl groups of the glucopyranose monomers that make up the cellulose backbone. It is often used as its sodiu ...

(Na-CMC), 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 A virucide (alternatively spelled viricide or named biocidal agent or known as microbicides or biocides) is any physical or chemical agent that deactivates or destroys viruses. The substances are not only virucidal but can be also bactericidal, fun ...

and fungicidal properties, thereby enabling TAED with percarbonate to

disinfect A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ste ...

and

deodorize Air fresheners are consumer products that typically emit fragrance and are used in homes or commercial interiors such as restrooms, foyers, hallways, vestibules and other smaller indoor areas, as well as larger areas such as hotel lobbies, auto ...

.Clariant Surfactant Division
The Clean and Clever Way of Bleaching - PERACTIVE
(PDF; 865 kB), 08.99

Ecology

Triacetylethylenediamine is mostly non-toxic and easily biodegradable. TAED and its byproduct DAED have low aquatic

ecotoxicity Ecotoxicity, the subject of study in the field of ecotoxicology (a portmanteau of ecology and toxicology), refers to the biological, chemical or physical stressors that affect ecosystems. Such stressors could occur in the natural environment at ...

. 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
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

References

External links

HERA RiskAssessment
Cleaning product components Acetamides