Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula HOCH 2CH 2NH 2 or C 2H 7NO.[8] The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscousliquid with an odor reminiscent of ammonia.[9] ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. It was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.[10]
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.[9]
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.
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.[14][18]
Other usesEdit
In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.[19]
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.[20]
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).[citation needed]
ReactionsEdit
Upon reaction with carbon dioxide, 2 equivalents of ethanolamine react through the intermediacy of carbonic acid to form a carbamate salt,[21] which when heated reforms ethanolamine and carbon dioxide.
ReferencesEdit
^ abNomenclature 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. ISBN978-0-85404-182-4. 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'.
^(PDF). Acros Organics. Archived from the original (PDF) on 2011-07-15.
^Hall, H.K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–4. doi:10.1021/ja01577a030.
^Reitmeier, R.E.; Sivertz, V.; Tartar, H.V. (1940). "Some Properties of Monoethanolamine and its Aqueous Solutions". Journal of the American Chemical Society. 62 (8): 1943–44. doi:10.1021/ja01865a009.
^"National Library of Medicine. PubChem. Ethanolomine". NIH, National Library of Medicine. Retrieved September 5, 2021.{{cite web}}: CS1 maint: url-status (link)
^ abMartin Ernst; Johann-Peter Melder; Franz Ingo Berger; Christian Koch (2022). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.pub2.
^"First evidence of cell membrane molecules in space". Astronomy Magazine. May 28, 2021. Retrieved September 4, 2021.{{cite web}}: CS1 maint: url-status (link)
^Coutinho, Bruna G.; Mevers, Emily; Schaefer, Amy L.; Pelletier, Dale A.; Harwood, Caroline S.; Clardy, Jon; Greenberg, E. Peter (2018-09-25). "A plant-responsive bacterial-signaling system senses an ethanolamine derivative". Proceedings of the National Academy of Sciences of the United States of America. 115 (39): 9785–9790. Bibcode:2018PNAS..115.9785C. doi:10.1073/pnas.1809611115. ISSN 0027-8424. PMC6166808. PMID 30190434.
^Marzo, V. Di; Petrocellis, L. De; Sepe, N.; Buono, A. (1996-06-15). "Biosynthesis of anandamide and related acylethanolamides in mouse J774 macrophages and N18 neuroblastoma cells". Biochemical Journal. 316 (Pt 3): 977–84. doi:10.1042/bj3160977. PMC1217444. PMID 8670178.
^Cough, Cold, and Allergy Preparation Toxicity at eMedicine
^ abcWeissermel, Klaus; Arpe, Hans-Jürgen; Lindley, Charlet R.; Hawkins, Stephen (2003). "Chap. 7. Oxidation Products of Ethylene". Industrial Organic Chemistry. Wiley-VCH. pp. 159–161. ISBN3-527-30578-5.
^. AOCS. Archived from the original on 2012-08-21. Retrieved 2015-08-09.
^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.
^Emergency and Continuous Exposure Guidance Levels for Selected Submarine Contaminants. 2007. doi:10.17226/11170. ISBN978-0-309-09225-8.
^Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes Cosméticos 4ª Ed. www.imagenpersonal.net. p. 306. ISBN978-84-613-4979-1.
^Federal Motor Vehicle Safety Standards. U.S. Department of Transportation, National Highway Traffic Safety Administration. 1994. p. Part 571; S 108—PRE 128.
^Lu, Yanyue; Liao, Anping; Yun, Zhuge; Liang, Yanqing; Yao, Qinmei (2014). "Absorption of Carbon Dioxide in Ethanolamine Solutions". Asian Journal of Chemistry. 26 (1): 39–42. doi:10.14233/ajchem.2014.15301.
External linksEdit
CDC - NIOSH Pocket Guide to Chemical Hazards
August 27, 2023
ethanolamine, aminoethanol, monoethanolamine, organic, chemical, compound, with, formula, hoch2, molecule, bifunctional, containing, both, primary, amine, primary, alcohol, colorless, viscous, liquid, with, odor, reminiscent, ammonia, molecules, component, for. Ethanolamine 2 aminoethanol monoethanolamine ETA or MEA is an organic chemical compound with the formula HOCH2 CH2 NH2 or C2 H7 NO 8 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 9 ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life It was thought to exist only on Earth and on certain asteroids but in 2021 evidence was found that ETA molecules exist in interstellar space 10 Ethanolamine NamesPreferred IUPAC name 2 Aminoethan 1 ol 1 Other names 2 Aminoethanol2 Amino 1 ethanolEthanolamine not recommended 1 Monoethanolamineb Aminoethanolb hydroxyethylamineb Aminoethyl alcoholGlycinolOlamineMEAEthylolamine2 HydroxyethylamineColamineIdentifiersCAS Number 141 43 5 Y3D model JSmol Interactive imageChEBI CHEBI 16000 YChEMBL ChEMBL104943 YChemSpider 13835336 YDrugBank DB03994 YECHA InfoCard 100 004 986EC Number 205 483 3KEGG D05074 YPubChem CID 700RTECS number KJ5775000UNII 5KV86114PT YCompTox Dashboard EPA DTXSID6022000InChI InChI 1S C2H7NO c3 1 2 4 h4H 1 3H2 YKey HZAXFHJVJLSVMW UHFFFAOYSA N YInChI 1 C2H7NO c3 1 2 4 h4H 1 3H2Key HZAXFHJVJLSVMW UHFFFAOYADSMILES NCCOPropertiesChemical formula C 2H 7N OMolar mass 61 084 g mol 1Appearance Viscous colourless liquidOdor Unpleasant ammonia like odourDensity 1 0117 g cm3Melting point 10 3 C 50 5 F 283 4 K Boiling point 170 C 338 F 443 K Solubility in water MiscibleVapor pressure 64 Pa 20 C 2 Acidity pKa 9 50 3 Refractive index nD 1 4539 20 C 4 HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H312 H314 H332 H335 H412 5 Precautionary statements P261 P273 P303 P361 P353 P305 P351 P338 5 NFPA 704 fire diamond 320Flash point 85 C 185 F 358 K closed cup Autoignitiontemperature 410 C 770 F 683 K Explosive limits 5 5 17 Lethal dose or concentration LD LC LD50 median dose 3320 mg kg rat oral 620 mg kg guinea pig oral 2050 mg kg rat oral 1475 mg kg mouse oral 1000 mg kg rabbit oral 700 mg kg mouse oral 1720 1970 mg kg rat oral 7 NIOSH US health exposure limits PEL Permissible TWA 3 ppm 6 mg m3 6 REL Recommended TWA 3 ppm 8 mg m3 ST 6 ppm 15 mg m3 6 IDLH Immediate danger 30 ppm 6 Safety data sheet SDS Sigma 5 Related compoundsRelated compounds N MethylethanolamineDiethanolamineTriethanolamineExcept 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 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 11 as well as precursor combined with arachidonic acid C20 H32 O2 20 4 w 6 to form the endocannabinoid anandamide AEA C22 H37 NO2 20 4 w 6 12 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 13 Contents 1 Industrial production 2 Biochemistry 3 Applications 3 1 Gas stream scrubbing 3 2 Other uses 3 3 pH control amine 4 Reactions 5 References 6 External linksIndustrial production EditMonoethanolamine 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 14 Biochemistry EditEthanolamine is biosynthesized by decarboxylation of serine 15 HOCH2 CH CO2 H NH2 HOCH2 CH2 NH2 CO2Ethanolamine 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 16 Applications EditEthanolamine 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 9 For example reacting ethanolamine with ammonia gives ethylenediamine a precursor of the commonly used chelating agent EDTA 14 Gas stream scrubbing Edit See also carbon dioxide scrubber and sour gas 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 17 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 14 18 Other uses Edit In pharmaceutical formulations MEA is used primarily for buffering or preparation of emulsions MEA can be used as pH regulator in cosmetics 19 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 20 pH control amine Edit 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 Reactions EditUpon reaction with carbon dioxide 2 equivalents of ethanolamine react through the intermediacy of carbonic acid to form a carbamate salt 21 which when heated reforms ethanolamine and carbon dioxide References Edit a b 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 Ethanolamine MSDS PDF Acros Organics Archived from the original PDF on 2011 07 15 Hall H K 1957 Correlation of the Base Strengths of Amines J Am Chem Soc 79 20 5441 4 doi 10 1021 ja01577a030 Reitmeier R E Sivertz V Tartar H V 1940 Some Properties of Monoethanolamine and its Aqueous Solutions Journal of the American Chemical Society 62 8 1943 44 doi 10 1021 ja01865a009 a b c Sigma Aldrich Co Ethanolamine Retrieved on 2018 05 24 a b c NIOSH Pocket Guide to Chemical Hazards 0256 National Institute for Occupational Safety and Health NIOSH Ethanolamine Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH National Library of Medicine PubChem Ethanolomine NIH National Library of Medicine Retrieved September 5 2021 a href Template Cite web html title Template Cite web cite web a CS1 maint url status link a b Martin Ernst Johann Peter Melder Franz Ingo Berger Christian Koch 2022 Ethanolamines and Propanolamines Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a10 001 pub2 First evidence of cell membrane molecules in space Astronomy Magazine May 28 2021 Retrieved September 4 2021 a href Template Cite web html title Template Cite web cite web a CS1 maint url status link Coutinho Bruna G Mevers Emily Schaefer Amy L Pelletier Dale A Harwood Caroline S Clardy Jon Greenberg E Peter 2018 09 25 A plant responsive bacterial signaling system senses an ethanolamine derivative Proceedings of the National Academy of Sciences of the United States of America 115 39 9785 9790 Bibcode 2018PNAS 115 9785C doi 10 1073 pnas 1809611115 ISSN 0027 8424 PMC 6166808 PMID 30190434 Marzo V Di Petrocellis L De Sepe N Buono A 1996 06 15 Biosynthesis of anandamide and related acylethanolamides in mouse J774 macrophages and N18 neuroblastoma cells Biochemical Journal 316 Pt 3 977 84 doi 10 1042 bj3160977 PMC 1217444 PMID 8670178 Cough Cold and Allergy Preparation Toxicity at eMedicine a b c Weissermel Klaus Arpe Hans Jurgen Lindley Charlet R Hawkins Stephen 2003 Chap 7 Oxidation Products of Ethylene Industrial Organic Chemistry Wiley VCH pp 159 161 ISBN 3 527 30578 5 Phosphatidylethanolamine and related lipids AOCS Archived from the original on 2012 08 21 Retrieved 2015 08 09 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 Emergency and Continuous Exposure Guidance Levels for Selected Submarine Contaminants 2007 doi 10 17226 11170 ISBN 978 0 309 09225 8 Ethanolamine Occupational Safety amp Health Administration Archived from the original on 2013 05 03 Retrieved 2008 05 11 Carrasco F 2009 Ingredientes Cosmeticos Diccionario de Ingredientes Cosmeticos 4ª Ed www imagenpersonal net p 306 ISBN 978 84 613 4979 1 Federal Motor Vehicle Safety Standards U S Department of Transportation National Highway Traffic Safety Administration 1994 p Part 571 S 108 PRE 128 Lu Yanyue Liao Anping Yun Zhuge Liang Yanqing Yao Qinmei 2014 Absorption of Carbon Dioxide in Ethanolamine Solutions Asian Journal of Chemistry 26 1 39 42 doi 10 14233 ajchem 2014 15301 External links EditProcess technology to produce ethanolamines by reaction of ammonia and ethylene oxide CDC NIOSH Pocket Guide to Chemical Hazards Retrieved from https en wikipedia org w index php title Ethanolamine amp oldid 1160306930, wikipedia, wiki, book, books, library,
