Triethylenediamine
[CAS# 280-57-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: Triethylenediamine
• Synonyms: 1,4-Diazabicyclo[2.2.2]octane; 2,2'-Diazabicyclo[2.2.2]octane
• Molecular Formula: C₆H₁₂N₂
• Molecular Weight: 112.17
• CAS Registry Number: 280-57-9
• EC Number: 205-999-9
• SMILES: C1CN2CCN1CC2

Properties

• Density: 1.14
• Melting point: 155-160 °C
• Boiling point: 174 °C
• Flash point: 62 °C
• Water solubility: 46 g/100 mL (26 °C)

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H315-H319-H361-H371-H372
• Safety Statements: P203-P260-P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P308+P316-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Flammable solids	Flam. Sol.	1	H228
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable solids	Flam. Sol.	2	H228
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	3	H336
Reproductive toxicity	Repr.	2	H361

• Transport Information: UN 1325

Discovery and Applications

Triethylenediamine, commonly abbreviated as TEDA, is a versatile chemical compound with the formula C₅H₁₂N₂. It is a diamine that consists of a central ethylene glycol backbone with two amine groups at the ends. This structure provides TEDA with its unique properties and wide range of applications.

The discovery of triethylenediamine can be attributed to the early 20th century when the development of complex organic compounds and their applications in various fields began to gain momentum. Researchers were exploring new types of amines for their potential uses in industrial processes, and TEDA emerged as a notable compound due to its useful chemical properties.

Triethylenediamine is primarily known for its role as a catalyst in the polymerization of isocyanates, particularly in the production of polyurethane. In this application, TEDA acts as a highly effective catalyst for the reaction between isocyanates and polyols, facilitating the formation of polyurethane foams, elastomers, and coatings. Its ability to accelerate the curing process and enhance the efficiency of the polymerization reaction makes it a valuable component in the production of these materials.

Another significant application of TEDA is in the field of organic synthesis, where it is used as a ligand in coordination chemistry. The presence of two amine groups in TEDA allows it to form chelate complexes with various metal ions, which are useful in a range of catalytic and synthetic processes. These complexes are employed in the synthesis of pharmaceuticals, fine chemicals, and other specialized compounds.

Triethylenediamine is also utilized in the production of epoxy resins, where it serves as a hardener or curing agent. In this context, TEDA helps to initiate and accelerate the cross-linking reaction between epoxy resins and hardeners, resulting in the formation of durable and heat-resistant polymer networks. This application is particularly valuable in industries such as aerospace, automotive, and electronics, where high-performance epoxy materials are required.

In addition to its industrial applications, TEDA is used in various research and development settings. It is a key reagent in the synthesis of novel chemical compounds and materials, contributing to advancements in chemistry and materials science. Its ability to form stable complexes and participate in diverse chemical reactions makes it a valuable tool for researchers exploring new chemical processes and materials.

The stability and effectiveness of triethylenediamine as a catalyst and reagent in various applications underscore its importance in industrial and research settings. Its ability to facilitate chemical reactions and improve process efficiency has made it a widely used compound in the production of polymers, resins, and fine chemicals.

In summary, triethylenediamine is a valuable chemical compound with a range of applications in polymerization, organic synthesis, and materials science. Its discovery and utilization have significantly contributed to advancements in these fields, highlighting its importance as a versatile and effective chemical substance.

References

2024. A multi-functional composite nanocatalyst for the synthesis of biologically active pyrazolopyranopyrimidines: Multifaceted antimicrobial, antioxidant, and anticancer activities. Journal of Molecular Structure, 1300.
DOI: 10.1016/j.molstruc.2023.137225

2012. Biomimetic, Mild Chemical Synthesis of CdTe-GSH Quantum Dots with Improved Biocompatibility. PLoS ONE, 7(1).
DOI: 10.1371/journal.pone.0030741

2007. On the Effect of 1,4-Diazabicyclo[2.2.2]octane on the Singlet-Oxygen Dimol Emission: Photosensitized Generation of (1O2)2. The Journal of Physical Chemistry A, 111(36).
DOI: 10.1021/jp0730585