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. The ...

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 betwee ...

(CH₃C(O))₂NCH₂CH₂N(C(O)CH₃)₂. This white solid is 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 ...

in laundry detergents and for paper pulp. It is produced by

acetylation : In organic 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 oppo ...

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 cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are more ...

s 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 anhydro ...

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 . I ...

, 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 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 a ...

, 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 aidin ...

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 drink, t ...

). 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 formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive. Peracetic a ...

. 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 The

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...

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 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 ...

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 Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, ...

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 d ...

.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