Ethanolamine

Occurrence in nature

MEA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. Ethanolamine is the second-most-abundant head group for phospholipids, substances found in biological membranes (particularly those of prokaryotes); e.g., phosphatidylethanolamine. It is also used in messenger molecules such as palmitoylethanolamide, which has an effect on CB1 receptors.

MEA was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that these molecules exist in interstellar space.

Ethanolamine is biosynthesized by decarboxylation of serine:

HOCH₂CH(CO₂H)NH₂ → H₂NCH₂CH₂OH + CO₂

Derivatives of ethanolamine are widespread in nature; e.g., lipids, as precursor of a variety of N-acylethanolamines (NAEs), that modulate several animal and plant physiological processes such as seed germination, plant–pathogen interactions, chloroplast development and flowering, as well as precursor, combined with arachidonic acid C₂₀H₃₂O₂ 20:4, ω-6), to form the endocannabinoid anandamide (AEA: C₂₂H₃₇NO₂; 20:4, ω-6).

MEA is biodegraded by ethanolamine ammonia-lyase, a B12-dependent enzyme. It is converted to ammonia and acetaldehyde via initial H-atom abstraction.

H₂NCH₂CH₂OH → NH₃ + CH₃CHO

Industrial production

Monoethanolamine is produced by treating ethylene oxide with aqueous ammonia; the reaction also produces diethanolamine and triethanolamine. The ratio of the products can be controlled by the stoichiometry of the reactants.

Applications

MEA is used as feedstock in the production of detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.

For example, reacting ethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent, EDTA.

Gas stream scrubbing

Monoethanolamines can scrub combusted-coal, combusted-methane and combusted-biogas flue emissions of carbon dioxide (CO₂) very efficiently. MEA carbon dioxide scrubbing is also used to regenerate the air on submarines.

Solutions of MEA in water are used as a gas stream scrubbing liquid in amine treaters. For example, aqueous MEA is used to remove carbon dioxide (CO₂) and hydrogen sulfide (H₂S) from various gas streams; e.g., flue gas and sour natural gas. The MEA ionizes dissolved acidic compounds, making them polar and considerably more soluble.

MEA scrubbing solutions can be recycled through a regeneration unit. When heated, MEA, being a rather weak base, will release dissolved H₂S or CO₂ gas resulting in a pure MEA solution.

Other uses

In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.

It is an injectable sclerosant as a treatment option of symptomatic hemorrhoids. 2–5 ml of ethanolamine oleate can be injected into the mucosa just above the hemorrhoids to cause ulceration and mucosal fixation thus preventing hemorrhoids from descending out of the anal canal.

It is also an ingredient in cleaning fluid for automobile windshields.

pH-control amine

Ethanolamine is often used for alkalinization of water in steam cycles of power plants, including nuclear power plants with pressurized water reactors. This alkalinization is performed to control corrosion of metal components. ETA (or sometimes a similar organic amine; e.g., morpholine) is selected because it does not accumulate in steam generators (boilers) and crevices due to its volatility, but rather distributes relatively uniformly throughout the entire steam cycle. In such application, ETA is a key ingredient of so-called "all-volatile treatment" of water (AVT).

Reactions

Upon reaction with carbon dioxide, 2 equivalents of ethanolamine react through the intermediacy of carbonic acid to form a carbamate salt, which when heated usually reforms back to ethanolamine and carbon dioxide but occasionally can also cyclizate to 2-oxazolidone, generating amine gas treatment wastes.