2-(2-Aminoethoxy)ethanol
[CAS# 929-06-6]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: 2-(2-Aminoethoxy)ethanol
• Synonyms: Diglycolamine; Diethylene glycolamine
• Molecular Formula: C₄H₁₁NO₂
• Molecular Weight: 105.14
• CAS Registry Number: 929-06-6
• EC Number: 213-195-4
• SMILES: C(COCCO)N

Properties

• Density: 1.05
• Melting point: -12.5 °C
• Boiling point: 218-224 °C
• Refractive index: 1.4585-1.4605
• Flash point: 127 °C
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H290-H314-H318
• Safety Statements: P234-P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	2	H371
Skin corrosion	Skin Corr.	1A	H314
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin irritation	Skin Irrit.	2	H315

• Transport Information: UN 3055; UN 1760

Discovery and Applications

2-(2-Aminoethoxy)ethanol, also known as diglycolamine (DGA), is an organic compound with the chemical formula C4H11NO2. This substance belongs to the class of amino alcohols, characterized by both an amine and alcohol functional group, making it highly reactive in a variety of chemical processes. It is a colorless, hygroscopic liquid, soluble in water and many organic solvents.

The discovery of 2-(2-Aminoethoxy)ethanol emerged from the study of alkanolamines in the early to mid-20th century. Its structure, featuring both amine and hydroxyl groups, made it a compound of interest for industrial applications where dual reactivity is beneficial. As industries sought to improve gas treatment processes, this substance became particularly relevant in addressing challenges related to gas purification.

One of the most significant applications of 2-(2-Aminoethoxy)ethanol is in the treatment of natural gas and other industrial gases, where it acts as an absorbent for acid gases such as carbon dioxide (CO2) and hydrogen sulfide (H2S). The compound is used in gas-sweetening processes, wherein it reacts with and removes these acidic impurities, thus improving the quality of the gas for commercial use. Its performance in this role is attributed to the presence of both the amine group, which reacts with acidic gases, and the alcohol group, which enhances its solubility in the solution phase.

Another major use of 2-(2-Aminoethoxy)ethanol is in the formulation of water-based coatings and cleaners, where its solvency and alkaline nature help in neutralizing acidic substances. In coatings, its ability to enhance the dispersion of pigments and resins improves the consistency and appearance of the final product. In cleaning products, it contributes to removing grease, oils, and other organic contaminants due to its combination of hydrophilic and hydrophobic properties.

The pharmaceutical and personal care industries have also found applications for 2-(2-Aminoethoxy)ethanol. In pharmaceuticals, it is sometimes used as a precursor in the synthesis of active compounds. Its utility in personal care formulations, particularly in creams and lotions, lies in its role as a solubilizer and emulsifying agent, allowing water and oil components to mix effectively.

In addition to its functional uses, the compound has gained attention for its potential role in the development of carbon capture technologies. As industries face increasing pressure to reduce CO2 emissions, materials like 2-(2-Aminoethoxy)ethanol offer promise in capturing and sequestering greenhouse gases from the atmosphere or industrial exhaust streams.

References

2023. A green amino acid-based solvent blended with diethanolamine solution for CO2 capture using micro-contactor. Brazilian Journal of Chemical Engineering, 40(4).
DOI: 10.1007/s43153-023-00348-5

1974. Soap-based detergent formulations: VI. Alkylaryl sulfonamide derivatives as lime soap dispersing agents. Journal of the American Oil Chemists' Society, 51(4).
DOI: 10.1007/bf02639721

1971. Sulfated diglycolamides. Journal of the American Oil Chemists' Society, 48(1).
DOI: 10.1007/bf02673239