Tetraacetylethylenediamine, commonly abbreviated as TAED, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

(CH₃C(O))₂NCH₂CH₂N(C(O)CH₃)₂. It is a white solid commonly used as a

bleach activator Bleach activators are compounds that allow a lower washing temperature than would be required otherwise to achieve the full activity of bleaching agents in the wash liquor. Bleaching agents, usually peroxides, are usually sufficiently active only ...

laundry detergents Laundry is the washing of clothing and other textiles, and, more broadly, their drying and ironing as well. Laundry has been part of history since humans began to wear clothes, so the methods by which different cultures have dealt with this uni ...

and in the production of

paper pulp Pulp is a fibrous lignocellulosic material prepared by chemically, semi-chemically, or mechanically isolating the cellulosic fibers of wood, fiber crops, waste paper, or rags. Mixed with water and other chemicals or plant-based additives, pul ...

. TAED is synthesized through the

acetylation : In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply ''acetates''. Deacetylation is the opposite react ...

ethylenediamine Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...

Use and mechanism of action

TAED is an important component of laundry

detergent A detergent is a surfactant or a mixture of surfactants with Cleanliness, cleansing properties when in Concentration, dilute Solution (chemistry), solutions. There are a large variety of detergents. A common family is the alkylbenzene sulfonate ...

s that use "active oxygen" bleaching agents. Active oxygen bleaching agents include

sodium perborate Sodium perborate are chemical compounds with chemical formula (H2O)x. Commonly encountered salts are the anhydrous form (x = 0) and as a hydrate, hexahydrate (x = 6). These two species are sometimes called, respectively, "monohydrate" or PBS-1 a ...

sodium percarbonate Sodium percarbonate or sodium carbonate peroxide is an inorganic compound with the formula . It is an adduct of sodium carbonate ("soda ash" or "washing soda") and hydrogen peroxide (that is, a perhydrate). It is a colorless, crystalline, hygros ...

, sodium perphosphate,

sodium persulfate Sodium persulfate is the inorganic compound with the formula Na2 S2 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 and has good shelf-life. ...

, 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 viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

during the wash cycle, but the release of

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

react to form

peroxyacetic acid Peracetic acid (also known as peroxyacetic acid, or Percidine) 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. Perac ...

, 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 aiding ...

Unilever Unilever PLC () is a British multinational consumer packaged goods company headquartered in London, England. It was founded on 2 September 1929 following the merger of Dutch margarine producer Margarine Unie with British soap maker Lever B ...

). 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 Percidine) 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. Perac ...

. 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 reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

, 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

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 inv ...

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 in 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 A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their p ...

virucidal A virucide (alternatively spelled viricide) is any physical or chemical agent that deactivates or destroys viruses. The substances are not only virucidal but can be also bactericidal, fungicidal, sporicidal or tuberculocidal. Virucides are t ...

and

fungicidal Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

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 endospore, bacterial spores; it is less effect ...

and deodorize.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 can occur in the natural environment at de ...

. 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