Template:Chembox Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula Template:Chem or Template:Chem.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.<ref name=Ullmann>Template:Ullmann</ref>
Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEOA). The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine.<ref>Template:EMedicine</ref>
HistoryEdit
Ethanolamines, or in particular, their salts, were discovered by Charles Adolphe Wurtz in 1860<ref>Template:Cite journal</ref> by heating 2-chloroethanol with ammonia solution while studying derivatives of ethylene oxide he discovered a year earlier.<ref name=":0">{{#if:9227912B2
|[{{#ifeq:|uspto|http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=%7Chttps://patents.google.com/patent/US}}{{#iferror:{{#expr:9227912B2 }}|9227912B2}} U.S. patent {{#ifeq:Template:Replace|Template:Digits|Template:Replace|9227912B2}}]
|{{US patent|123456|link text}}}}</ref> He wasn't able to separate the salts or isolate any free bases.
In 1897 Ludwig Knorr developed the modern industrial route (see below) and separated the products, including MEA, by fractional distillation, for the first time studying their properties.<ref>Template:Cite journal</ref>
None of the ethanolamines were of any commercial importance until after the WWII industrial production of ethylene oxide took off.<ref name=":0" />
Occurrence in natureEdit
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.<ref>Template:Cite journal</ref>
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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
Ethanolamine is biosynthesized by decarboxylation of serine:<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
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,<ref>Template:Cite journal</ref> as well as precursor, combined with arachidonic acid Template:Chem 20:4, ω-6), to form the endocannabinoid anandamide (AEA: Template:Chem; 20:4, ω-6).<ref>Template:Cite journal</ref>
MEA is biodegraded by ethanolamine ammonia-lyase, a B12-dependent enzyme. It is converted to acetaldehyde and ammonia via initial H-atom abstraction.<ref>Template:Cite journal</ref>
Industrial productionEdit
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.<ref name = weissermel/>
ApplicationsEdit
MEA is used as feedstock in the production of detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.<ref name=Ullmann/>
For example, reacting ethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent, EDTA.<ref name = weissermel/>
Gas stream scrubbingEdit
Template:See also Monoethanolamines can scrub combusted-coal, combusted-methane and combusted-biogas flue emissions of carbon dioxide (Template: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.<ref name="Chremos2014">Template:Cite journal</ref> For example, aqueous MEA is used to remove carbon dioxide (Template:CO2) and hydrogen sulfide (Template:H2S) from various gas streams; e.g., flue gas and sour natural gas.<ref>Template:Cite book</ref> 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 Template:H2S or Template:CO2 gas resulting in a pure MEA solution.<ref name = weissermel>Template:Cite book</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
Other usesEdit
In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.<ref name=Carrasco>Template:Cite book</ref>
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.<ref>Template:Cite book</ref>
pH-control amineEdit
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).Template:Citation needed
ReactionsEdit
Upon reaction with carbon dioxide, 2 equivalents of ethanolamine react through the intermediacy of carbonic acid to form a carbamate salt,<ref>Template:Cite journal</ref> which when heated usually reforms back to ethanolamine and carbon dioxide but occasionally can also cyclizate to 2-oxazolidone, generating amine gas treatment wastes.<ref>Template:Cite journal</ref>