Tetraacetylethylenediamine
[CAS# 10543-57-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: Tetraacetylethylenediamine
• Synonyms: N,N'-Ethylenebis(diacetamide); T.A.E.D.
• Molecular Formula: C₁₀H₁₆N₂O₄
• Molecular Weight: 228.25
• CAS Registry Number: 10543-57-4
• EC Number: 234-123-8
• SMILES: CC(=O)N(CCN(C(=O)C)C(=O)C)C(=O)C

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 149-153 °C (Expl.)
• Index of Refraction: 1.481, Calc.^*
• Boiling Point: 386.4±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 174.8±15.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Discovery and Applications

Tetraacetylethylenediamine (TAED) is an organic compound with the molecular formula C₁₀H₁₆N₂O₄. It is a white crystalline solid with good solubility in organic solvents and limited solubility in water. TAED is synthesized through the acetylation of ethylenediamine using acetic anhydride or related acetylating agents under controlled reaction conditions.

TAED is primarily used as a bleaching activator in household and industrial laundry detergents. It enhances the efficiency of peroxygen-based bleaching agents, such as sodium percarbonate and sodium perborate, by generating peracetic acid in aqueous solutions. This reaction occurs at relatively low temperatures, making TAED an essential component in cold-water washing formulations. The use of TAED in detergents improves stain removal and fabric whitening while reducing the need for high-temperature washing, thereby contributing to energy savings.

Beyond its application in detergents, TAED has been utilized in the textile and paper industries, where it plays a role in environmentally friendly bleaching processes. It aids in delignification and brightening while minimizing damage to fibers and reducing the formation of harmful byproducts.

TAED has also been studied for its role in wastewater treatment, where it facilitates oxidative degradation of organic contaminants. The compound's ability to generate peracetic acid under mild conditions has been employed in certain disinfection and sanitation processes, contributing to its relevance in hygiene applications.

Due to its biodegradable nature and low toxicity, TAED has been considered an environmentally compatible bleaching activator. Its decomposition products include ethylenediamine and acetic acid, both of which are relatively benign compared to traditional chlorine-based bleaching agents.

TAED continues to be widely used in detergent formulations and related industries due to its effectiveness in activating peroxygen-based bleaching systems. Its well-documented role in enhancing oxidative processes has solidified its importance in cleaning, sanitation, and industrial applications.

References

2024. Inventory of aqueous and sediment-associated organic pollutants released by the 2021 flood in the Vicht-Inde catchment, Germany. Environmental Sciences Europe, 36(1).
DOI: 10.1186/s12302-024-00925-6

2020. Potential bleach activators with improved imide hydrolytic stability. International Journal of Industrial Chemistry, 11(3).
DOI: 10.1007/s40090-020-00210-4

2013. The TAED/H2O2/NaHCO3 system as an approach to low-temperature and near-neutral pH bleaching of cotton. Carbohydrate Polymers, 95(1).
DOI: 10.1016/j.carbpol.2013.02.061