Ethanolamine
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Preferred IUPAC name 2-Aminoethan-1-ol[1] | |
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ECHA InfoCard | 100.004.986 |
EC Number | 205-483-3 |
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RTECS number | KJ5775000 |
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| Properties | |
Chemical formula | C2H7NO |
Molar mass | 61.08 g·mol−1 |
| Appearance | Viscous colourless liquid |
Odor | Unpleasant ammonia-like odour |
Density | 1.0117 g/cm3 |
Melting point | 10.3 °C (50.5 °F; 283.4 K) |
Boiling point | 170 °C (338 °F; 443 K) |
Solubility in water | Miscible |
Vapor pressure | 64 Pa (20 °C)[2] |
Acidity (pKa) | 9.50[3] |
Refractive index (nD) | 1.4539 (20 °C)[4] |
| Hazards | |
Safety data sheet | Sigma[5] |
GHS pictograms |   |
GHS signal word | Danger |
GHS hazard statements | H302, H312, H332, H314, H335, H412[5] |
GHS precautionary statements | P261, P273, P305+351+338, P303+361+353[5] |
NFPA 704 |  2 3 0 |
Flash point | 85 °C (185 °F; 358 K) (closed cup) |
Autoignition temperature | 410 °C (770 °F; 683 K) |
Explosive limits | 5.5–17% |
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LD50 (median dose) |
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| US health exposure limits (NIOSH): | |
PEL (Permissible) | TWA: 3 ppm (6 mg/m3)[6] |
REL (Recommended) |
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IDLH (Immediate danger) | 30 ppm[6] |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 Y verify (what is  Y N ?) | |
Infobox references | |
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula HOCH2CH2NH2. 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.[8] Its derivatives are widespread in nature; e.g., lipids.
The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, diphenhydramine, and doxylamine.[9]
Contents
1 Industrial production
2 Biochemistry
3 Applications
3.1 Gas stream scrubbing
3.2 Other uses
3.3 pH-control amine
4 References
5 External links
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.[10]
Biochemistry
Ethanolamine is biosynthesized by decarboxylation of serine:[11]
- HOCH2CH(CO2H)NH2 → HOCH2CH2NH2 + CO2
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.[12]
Applications
Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEA). It is used as feedstock in the production of detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.[8]
For example, reacting ethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent, EDTA.[10]
Gas stream scrubbing
Like other amines, monoethanolamine is a weak base and this property is exploited in its use in gas scrubbing. Monoethanolamines can scrub combusted coal, combusted methane and combusted biogas flue emissions of carbon dioxide (CO2) very efficiently. Monoethanolamine scrubbing reduces climate change and can make historical coal and biogas industry more modern, healthier and more marketable. Legally, it is especially relevant to the Paris Agreement. MEA carbon dioxide scrubbing is also used to regenerate the air on submarines.
Aqueous solutions of MEA (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.[13]. 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. [10][14]
Other uses
In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.[15]
It is also 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.
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).[citation needed]
References
^ ab Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 649, 717. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.For example, the name ‘ethanolamine’, which is still widely used, is badly constructed because of the presence of two suffixes; it is not an alternative to the preferred IUPAC name, ‘2-aminoethan-1-ol’.
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^ "Ethanolamine MSDS" (PDF). Acros Organics. Archived from the original (PDF) on 2011-07-15.
^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
^ R. E. Reitmeier; V. Sivertz; H. V. Tartar (1940). "Some Properties of Monoethanolamine and its Aqueous Solutions". Journal of the American Chemical Society. 62 (8): 1943–1944. doi:10.1021/ja01865a009.
^ abc Sigma-Aldrich Co., Ethanolamine. Retrieved on 2018-05-24.
^ abc "NIOSH Pocket Guide to Chemical Hazards #0256". National Institute for Occupational Safety and Health (NIOSH).
^ "Ethanolamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ ab Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.CS1 maint: Uses authors parameter (link)
^ Cough, Cold, and Allergy Preparation Toxicity at eMedicine
^ abc Klaus Weissermel; Hans-Jürgen Arpe; Charlet R. Lindley; Stephen Hawkins (2003). "Chap. 7. Oxidation Products of Ethylene". Industrial Organic Chemistry. Wiley-VCH. pp. 159–161. ISBN 3-527-30578-5.
^ http://lipidlibrary.aocs.org/Lipids/pe/index.htm
^ Calignano, A; La Rana, G; Piomelli, D (2001). "Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide". European Journal of Pharmacology. 419 (2–3): 191–8. doi:10.1016/S0014-2999(01)00988-8. PMID 11426841.
^ http://www.nap.edu/openbook.php?record_id=11170[full citation needed]
^ "Ethanolamine". Occupational Safety & Health Administration.
^ Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes Cosméticos 4ª Ed. www.imagenpersonal.net. p. 306. ISBN 978-84-613-4979-1.
External links
- Process technology to produce ethanolamines by reaction of ammonia and ethylene oxide
- CDC - NIOSH Pocket Guide to Chemical Hazards
