Tetraacetylethylenediamine

Last updated
Tetraacetylethylenediamine
Tetraacetylethylenediamine.svg
Tetraacetylethylenediamine Ball and Stick.png
Names
Preferred IUPAC name
N,N′-(Ethane-1,2-diyl)bis(N-acetylacetamide)
Other names
TAED, N,N′-ethylenebis(diacetamide)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.031.009 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H16N2O4/c1-7(13)11(8(2)14)5-6-12(9(3)15)10(4)16/h5-6H2,1-4H3 X mark.svgN
    Key: BGRWYDHXPHLNKA-UHFFFAOYSA-N X mark.svgN
  • 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
  • O=C(C)N(C(C)=O)CCN(C(C)=O)C(C)=O
Properties
C10H16N2O4
Molar mass 228.248 g·mol−1
AppearanceColorless solid
Density 0.9
Melting point 149 to 154 °C (300 to 309 °F; 422 to 427 K)
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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 percarbonate, sodium perphosphate, sodium persulfate, and urea peroxide. These compounds release hydrogen peroxide during the wash cycle, but the release of hydrogen peroxide is low when these compounds used in temperatures below 45 °C (113 °F). TAED and hydrogen peroxide react 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). [1] Currently, TAED is the main bleach activator used in European laundry detergents and has an estimated annual consumption of 75 kt. [2]

Perhydrolysis

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): [3]

Peracetic acid production from the hydrogen peroxide and TAED.svg

TAED typically provides only two equivalents of peracetic acid, although four are theoretically possible. [4] Competing with perhydrolysis, TAED also undergoes some hydrolysis, which is an unproductive pathway. [5] [6]

Preparation

TAED is prepared in a two-stage process from ethylenediamine and acetic anhydride. The process is nearly quantitative. [7] [8] [9]

TAED 2-step-synthesis.svg

Properties

Powdered TAED is stabilized by granulation with the aid of the sodium salt of carboxymethylcellulose (Na-CMC), [10] 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 and fungicidal properties, thereby enabling TAED with percarbonate to disinfect and deodorize. [11]

Ecology

Triacetylethylenediamine is mostly non-toxic and easily biodegradable. TAED and its byproduct DAED have low aquatic ecotoxicity. 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. [12] TAED, TriAED and DAED are all completely biodegradable and substantially removed during wastewater treatment. [13]

Related Research Articles

<span class="mw-page-title-main">Detergent</span> Surfactants with cleansing properties

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 soluble in hard water, because the polar sulfonate is less likely than the polar carboxylate to bind to calcium and other ions found in hard water.

<span class="mw-page-title-main">Sodium percarbonate</span> Chemical compound

Sodium percarbonate is a chemical substance with formula Na
2H
3CO
6. It is an adduct of sodium carbonate and hydrogen peroxide whose formula is more properly written as 2 Na
2CO
3 · 3 H
2O
2. It is a colorless, crystalline, hygroscopic and water-soluble solid. It is sometimes abbreviated as SPC. It contains 32.5% by weight of hydrogen peroxide.

<span class="mw-page-title-main">Hydrogen peroxide - urea</span> Chemical compound

Hydrogen peroxide - urea is a solid composed of equal amounts of hydrogen peroxide and urea. This compound is a white crystalline solid which dissolves in water to give free hydrogen peroxide. Hydrogen peroxide - urea contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in the dental office, it is used as a source of hydrogen peroxide for bleaching, disinfection, and oxidation.

<span class="mw-page-title-main">OxiClean</span> American brand of household cleaners

OxiClean is an American brand of household cleaners, including OxiClean Versatile Stain Remover, which is a laundry additive, spot stain remover, and household cleaner marketed by Church & Dwight. It was formerly owned by Orange Glo International from its introduction in 1997 until it was acquired in 2006.

<span class="mw-page-title-main">Laundry detergent</span> Type of detergent used for cleaning laundry

Laundry detergent is a type of detergent used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder and liquid form.

Sodium perborate is chemical compound whose chemical formula may be written NaH2BO4, Na2H4B2O8, or, more properly, [Na+]2[B2O4(OH)4]2−. Its name is sometimes abbreviated as PBS.

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.

Sodium nonanoyloxybenzenesulfonate (NOBS) is an important component of laundry detergents and bleaches. It is known as a bleach activator for active oxygen sources, allowing formulas containing hydrogen peroxide releasing chemicals to effect bleaching at lower temperatures.

<span class="mw-page-title-main">Bleach</span> Chemical used to remove stains, whiten, or disinfect, often via oxidation

Bleach is the generic name for any chemical product that is used industrially or domestically to remove color (whitening) from a fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.

Stain removal is the process of removing a mark or spot left by one substance on a specific surface like a fabric. A solvent or detergent is generally used to conduct stain removal and many of these are available over the counter.

Pyridine-<i>N</i>-oxide Chemical compound

Pyridine-N-oxide is the heterocyclic compound with the formula C5H5NO. This colourless, hygroscopic solid is the product of the oxidation of pyridine. It was originally prepared using peroxyacids as the oxidising agent. The compound is used infrequently as an oxidizing reagent in organic synthesis.

<span class="mw-page-title-main">Retrobright</span> Removing yellowing from plastic

Retrobright refers to H2O2 (hydrogen peroxide) based processes used to remove yellowing from ABS plastics. The usage has also expanded to other retro restoration applications, such as classic and collectible sneaker restoration, where it is referred to by collectors as "sole sauce".

<span class="mw-page-title-main">Bleach activator</span>

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 at 60 °C and up. With bleach activators, this activity can be achieved at lower temperatures. Bleach activators are included in some laundry detergent powders, some laundry additive powders, and a few laundry additive pods. They are not included in any liquid laundry detergents. Bleach activators react with hydrogen peroxide in aqueous solution to form peroxy acids. Peroxy acids are more active bleaches than hydrogen peroxide at lower temperatures (<60 °C), but are too unstable to be stored in their active form, and hence must be generated in situ.

<span class="mw-page-title-main">Tetraethoxymethane</span> Chemical compound

Tetraethoxymethane is a chemical compound which is formally formed by complete ethylation of the hypothetical orthocarbonic acid C(OH)4 (orthocarboxylic acid violates the Erlenmeyer rule and is unstable in free state).

<span class="mw-page-title-main">Metal peroxide</span>

Metal peroxides are metal-containing compounds with ionically- or covalently-bonded peroxide (O2−
2) groups. This large family of compounds can be divided into ionic and covalent peroxide. The first class mostly contains the peroxides of the alkali and alkaline earth metals whereas the covalent peroxides are represented by such compounds as hydrogen peroxide and peroxymonosulfuric acid (H2SO5). In contrast to the purely ionic character of alkali metal peroxides, peroxides of transition metals have a more covalent character.

<span class="mw-page-title-main">Tetrasodium iminodisuccinate</span> Chemical compound

Tetrasodiumiminodisuccinate is a sodium salt of iminodisuccinic acid, also referred to as N-(1,2-dicarboxyethyl)aspartic acid.

A peroxide-based bleach or simply peroxide bleach is any bleach product that is based on the peroxide chemical group, namely two oxygen atoms connected by a single bond, (–O–O–). This bond is fairly weak and is often broken in chemical reactions of peroxides, giving rise to very reactive oxygen species, which are the active agents of the bleach.

<span class="mw-page-title-main">Trisodium dicarboxymethyl alaninate</span> Chemical compound

Trisodium N-(1-carboxylatoethyl)iminodiacetate, methylglycinediacetic acid trisodium salt (MGDA-Na3) or trisodium α-DL-alanine diacetate (α-ADA), is the trisodium anion of N-(1-carboxyethyl)iminodiacetic acid and a tetradentate complexing agent. It forms stable 1:1 chelate complexes with cations having a charge number of at least +2, e.g. the "hard water forming" cations Ca2+ or Mg2+. α-ADA is distinguished from the isomeric β-alaninediacetic acid by better biodegradability and therefore improved environmental compatibility.

References

  1. ↑ Smulders E.; von Rybinski W.; Sung E.; Rähse W.; Steber J.; Wiebel F.; Nordskog A. (2002). "Laundry Detergents". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH.
  2. ↑ Reinhardt, G.; Borchers, G. (2009). "Application of Bleaching Detergent Formulations". In Zoller, Uri (ed.). Handbook of Detergents Part E: Applications. USA: CRC Press. ISBN   9781574447576.
  3. ↑ 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.
  4. ↑ Farr, J. P.; Smith, W. L.; Steichen,, D. S. (1992). "Bleaching Agents". Kirk-Othmer Encyclopedia of Chemical Technology Vol. 4 (4th ed.). John Wiley & Sons, Inc. pp. 271–299.{{cite book}}: CS1 maint: multiple names: authors list (link)
  5. ↑ Hauthal, G. H., Schmidt, H., Scholz, J., Hofmann, J. and Pritzkow W. (1990). "Studies concerning the mechanism of bleach activation". Tenside Surf. Det. 27 (3). doi:10.1515/tsd-1990-270314. S2CID   235325458.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ↑ Hofmann, J., Just, G., Pritzkow, W. and Schmidt, H. (1992). "Bleaching activators and the mechanism of bleaching activation". Journal für Praktische Chemie/Chemiker-Zeitung. 334 (4): 293–297. doi:10.1002/prac.19923340402.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ↑ 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
  8. ↑ Europäische Patentanmeldung EPA 0 051 739 A1, Verfahren zur Herstellung von N,N,N’,N’-Tetraacetylethylendiamin, Erfinder: W. Köhler et al., Anmelder: BASF AG, veröffentlicht am 19. Mai 1982
  9. ↑ Europäisches Patent EP 0 238 958 B1, Verfahren zur Reinigung von Tetraacetylethylendiamin, Erfinder: K. Köster, F.-J. Carduck, Anmelder: Henkel KG aA, veröffentlicht am 12. Juni 1991
  10. ↑ US-Patent US 5,100,576, Process for the preparation of a readily soluble bleach activator granulate with a long shelf life, Erfinder: J. Cramer et al., Anmelder: Hoechst AG, erteilt am 31. März 1992.
  11. ↑ Clariant Surfactant Division: The Clean and Clever Way of Bleaching - PERACTIVE Archived 2013-07-17 at the Wayback Machine (PDF; 865 kB), 08.99
  12. ↑ HERA Human & Environmental Risk Assessment on ingredients of European household cleaning products: Tetraacetylethylenediamine (TAED), CAS 10543-57-4 (PDF; 666 kB), Draft, DECEMBER 2002.
  13. ↑ Gilbert, P. A. (1992). "TAED-Tetraacetylethylenediamine". In de Oude, N. T. (ed.). The Handbook of Environmental Chemistry, Vol. 3 Part F Antropogenic Compounds: Detergents. Berlin: Springer-Verlag. ISBN   354053797X.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.