10543-57-4

Basic information

• Product Name: Tetraacetylethylenediamine
• Synonyms: n,n’-1,2-ethanediylbis[n-acetyl-acetamid;N,N’-1,2-ethanediylbis[N-acetyl-Acetamide;N,N’-1,2-ethanediylbis[N-acetylacetamide];N,N’-ethylenebis[N-acetylacetamide];N-Acetyl-N-[2-(diacetylamino)ethyl]acetamide;TetraAcetylEthyleneDiamine(Taed);TEAD;TETRAACETYLENEDIAMINE
• CAS NO: 10543-57-4
• Molecular Formula: C₁₀H₁₆N₂O₄
• Molecular Weight: 228.25
• EINECS: 234-123-8
• Product Categories: Daily Chemical Usage
• Mol File: 10543-57-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 149-154 °C
• Boiling Point: 140 °C (1.5002 mmHg)
• Flash Point: 140 °C
• Appearance: Off-white to beige/Granular Powder
• Density: 0.9
• Refractive Index: 1.4550 (estimate)
• PKA: -1.23±0.70(Predicted)
• Water Solubility: slightly soluble
• Merck: 14,9028
• BRN: 1795711
• CAS DataBase Reference: Tetraacetylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraacetylethylenediamine(10543-57-4)
• EPA Substance Registry System: Tetraacetylethylenediamine(10543-57-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 10543-57-4(Hazardous Substances Data)

Usage

Chemical Properties

Tetraacetylethylenediamine is off-white to beige granular powder

Uses

Different sources of media describe the Uses of 10543-57-4 differently. You can refer to the following data:
1. Tetraacetylethylenediamine (TAED) is a bleaching activator which is mainly used in detergents and additives for laundry washing and dishwashing. Typical concentrations of TAED range between 1.4% and 13% in these products. A small amount of the produced TAED is also used in bleaching of paper, textiles and for the generation of Peracetic acid. Peroxide bleach activator for household detergents, paper pulp.
2. N,N,N',N'-Tetraacetylethylenediamine is used as a peroxide bleach activator in household detergents and for paper pulp. It also serves as an important component of laundry detergents and bleaches, where it is used as an activator for active oxygen bleaching agents such as sodium perborate, sodium percarbonate, sodium perphosphate and sodium persulfate. It reacts with the perhydroxyl anion HO2- in the presence of aqueous alkaline solution to prepare triacetylethylenediamine and diacetylethylenediamine with the release of peracetic acid, which is a fast acting bleaching agent.

Preparation

Tetraacetylethylenediamine (TAED) is produced in a two stage process from ethylenediamine (ED) and acetic anhydride (Ac2O). ED is first diacetylated to DAED. In the second step DAED is subsequently converted with Ac2O via TriAED into TAED (Clariant, 1999). TAED is crystallized out of the reaction mixture, filtered, washed and dried, and if necessary also granulated. The raw materials used occur almost quantitatively in the product. Byproducts are not formed. TAED was prepared by acetylation of diacetylethylenediamine (DAED) with acetic anhydride in a 5 L reactor coupled with a packed distillation column, 2.5 cm in inside diameter and 1 m in length. The reaction temperature was set at 135 °C and the reflux ratio at 6. The molar ratio of acetic anhydride to DAED was varied from 3 to 5. A TAED yield as high as 80% was obtained, higher by 15% than in the absence of distillation.

Health Hazard

TAED is of very low toxicity by all exposure routes examined. Up to 2 g/kg BW there is no acute toxicity. TAED is practically non-irritating to skin and eyes and there is no evidence of a sensitizing potential by skin contact. The only effect after repeated oral and dermal dosing was reversible centrilobular hypertrophy in the liver at high doses due to the induction of metabolizing enzymes. In a 90-day whole body inhalation study no adverse effects in the rat lung, respiratory tract or nasal mucosa were observed. Biokinetic data showed that TAED is rapidly absorbed from the rat intestine and largely metabolized via diacetylation to TriAED and DAED which are excreted in the urine.

Synthetic route

N,N'-diacetylethylenediamine (871-78-3) + acetic anhydride (108-24-7) → N,N,N',N'-tetraacetylethylenediamine (10543-57-4)

Conditions	Yield
With solid acid SO4(2-)/Al2O3 at 110 - 160℃; for 4.5h; Reagent/catalyst; Temperature;	81.9%

acetic anhydride (108-24-7) + N.N'-diacetyl-ethylenediamine → N,N,N',N'-tetraacetylethylenediamine (10543-57-4)

N,Ν,Ν'-triacetylenediamine (137706-80-0) + acetic anhydride (108-24-7) → N,N,N',N'-tetraacetylethylenediamine (10543-57-4) + acetic acid (64-19-7)

Conditions	Yield
at 140℃; Kinetics; Temperature;

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → peracetic acid (79-21-0)

Conditions	Yield
With dihydrogen peroxide; sodium carbonate; sodium hydroxide In water	52.56%
With dihydrogen peroxide In water

piperidine (110-89-4) + N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → 1-piperidin-1-yl-ethanone (618-42-8)

Conditions	Yield
In 1,4-dioxane at 60℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → peracetic acid (79-21-0) + N,Ν,Ν'-triacetylenediamine (137706-80-0)

Conditions	Yield
With 1,2-ethanediylbistetraphosphonic acid; dihydrogen peroxide at 25℃; Rate constant; pH 9.60 (carbonate buffer);

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → N,Ν,Ν'-triacetylenediamine (137706-80-0)

Conditions	Yield
With peracetic acid at 25℃; Rate constant; carbonate buffer;

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → N,Ν,Ν'-triacetylenediamine (137706-80-0) + acetic acid (64-19-7)

Conditions	Yield
With water at 25℃; Rate constant; pH 9.60 and 10.47 (carbonate buffer);

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → N,N'-diacetylethylenediamine (871-78-3) + N,Ν,Ν'-triacetylenediamine (137706-80-0)

Conditions	Yield
With iron(III) perchlorate In water at 20℃; for 480h; pH=2.9 - 5.5; Kinetics; Hydrolysis;

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) → peracetic acid (79-21-0) + acetic acid (64-19-7)

Conditions	Yield
With water; dihydrogen peroxide pH=5 - ~ 10.5; Reactivity; Potassium phosphate 50 mM; Potassium chloride 20 mM; polyester fabric;

N,N,N',N'-tetraacetylethylenediamine (10543-57-4) + acetic acid (64-19-7) → N,Ν,Ν'-triacetylenediamine (137706-80-0) + acetic anhydride (108-24-7)

Conditions	Yield
at 140℃; Kinetics; Temperature;

Upstream product

• 871-78-3 N,N'-diacetylethylenediamine 
• 108-24-7 acetic anhydride 
• 137706-80-0 N,Ν,Ν'-triacetylenediamine 

Downstream Products

• 871-78-3 N,N'-diacetylethylenediamine 
• 137706-80-0 N,Ν,Ν'-triacetylenediamine 
• 108-24-7 acetic anhydride 
• 79-21-0 peracetic acid 
• 64-19-7 acetic acid 
• 618-42-8 1-piperidin-1-yl-ethanone 

Related news

Characterization of hemicelluloses isolated with Tetraacetylethylenediamine (cas 10543-57-4) activated peroxide from ultrasound irradiated and alkali pre-treated wheat straw08/08/2019

Post-treatment with 2% H2O2–0.2% tetraacetylethylenediamine (TAED) at pH 11.8 for 12 h at 48 °C solubilized 27.1–28.1% of the original hemicelluloses and 43.3–46.2% of the original lignin from the ultrasound irradiated and alkali pre-treated wheat straw. It was found that the bleaching activ...detailed

Degradation and photodegradation of Tetraacetylethylenediamine (cas 10543-57-4) (TAED) in the presence of iron (III) in aqueous solution08/07/2019

The dark degradation of tetraacetylethylenediamine (TAED) was investigated. It is a slow process which is favored in acidic medium. There is a hydrolysis of an imide group with the scission of the CN bond giving rise to the triacetyl derivative (TAED'). When allowed to stand for longer ti...detailed

Treatment of chemical warfare agents by combined sodium percarbonate with Tetraacetylethylenediamine (cas 10543-57-4) solution08/06/2019

Treatment of chemical warfare agents (CWAs) including soman (GD), mustard (HD) and VX by combined sodium percarbonate and tetraacetylethylenediamine (SPC/TAED) solution was investigated. The optimal pH value for the degradation of HD and VX were about 7.5–9.0 and 8.5–9.5, respectively. The dec...detailed

Relevant articles and documents

Kinetic model of acylation of diacetylethylenediamine

Descriptive kinetics of synthesis of tetraacetylethylenediamine by acylation of diacetylethylenediamine with acetic acid anhydride was examined. The apparent rate constants of the process were obtained, and a mathematical model adequately describing the process was constructed.