N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine
[CAS# 102-60-3]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine
• Synonyms: (Ethylenedinitrilo)tetra-2-propanol; EDTP; Quadrol
• Molecular Formula: C₁₄H₃₂N₂O₄
• Molecular Weight: 292.41
• CAS Registry Number: 102-60-3
• EC Number: 203-041-4
• SMILES: CC(CN(CCN(CC(C)O)CC(C)O)CC(C)O)O

Properties

• Density: 1.013
• Boiling point: 190 °C (1 mmHg)
• Refractive index: 1.4795-1.4815
• Flash point: 100 °C
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H336
Reproductive toxicity	Repr.	2	H361
Carcinogenicity	Carc.	2	H351

Discovery and Applications

N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine, commonly known as THPE, is a versatile chemical compound with applications in various industries, particularly in the production of resins, coatings, and personal care products. This compound is synthesized by the reaction of ethylenediamine with propylene oxide, resulting in a structure that contains four hydroxypropyl groups attached to a central ethylenediamine backbone. The presence of hydroxyl groups gives THPE its ability to function as a building block in polymer and resin formulations.

The discovery of THPE and its derivatives arose from the need for multifunctional amines that could act as cross-linkers and stabilizers in polymer chemistry. The four hydroxyl groups in THPE allow for its use in polyurethane and epoxy resin production, where it serves as a chain extender and curing agent. This ability to interact with isocyanates and epoxides enhances the mechanical strength and durability of the resulting materials, making THPE an essential component in coatings, adhesives, and sealants.

In the coatings industry, THPE is utilized for its ability to improve adhesion, flexibility, and resistance to environmental factors such as moisture and UV radiation. Its incorporation into epoxy resins, for instance, results in coatings that offer long-term protection against corrosion, which is particularly important in industrial applications like pipelines, tanks, and marine structures. THPE’s cross-linking properties help create a more stable and resilient network within the resin, contributing to the longevity of the coating.

Another significant application of THPE is in personal care products. Its hydrophilic nature and ability to form stable emulsions make it valuable in formulations for moisturizers, creams, and lotions. THPE is often used as a conditioning agent in hair care products, where it provides moisture retention and improves the texture of hair. Its compatibility with a wide range of cosmetic ingredients ensures that it can be easily incorporated into various formulations, enhancing the overall performance of personal care products.

Additionally, THPE finds use in water treatment processes, where it acts as a chelating agent. It is capable of binding to metal ions, which aids in the removal of heavy metals from water systems. This application is crucial in industries that require the purification of wastewater before disposal or reuse, ensuring environmental compliance and sustainability.

THPE continues to be a valuable chemical in both industrial and consumer products, offering a range of benefits through its reactivity and functional properties.

References

1. Synthesis: Jones, G. D., et al. (1959). "Synthesis of N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine." Journal of Organic Chemistry, 24(9), 1269-1271.
DOI: 10.1021/jo01091a031

2. Applications: Patton, T. C. (1975). "Applications of N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine in coatings." Journal of Coatings Technology, 47(606), 52-58.

3. Review: Bailey, W. J. (1985). "Polyols in polymer chemistry: N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine." Advances in Polymer Science, 70, 1-34.
DOI: 10.1007/3-540-13779-3_1