Ethanolamine

Ethanolamine
Names
	Preferred IUPAC name 2-Aminoethan-1-ol
	Other names 2-Aminoethanol; 2-Amino-1-ethanol; Ethanolamine (not recommended); Monoethanolamine; β-Aminoethanol; β-hydroxyethylamine; β-Aminoethyl alcohol; Glycinol; Olamine; MEA; Ethylolamine; 2-Hydroxyethylamine; Colamine;
Identifiers
CAS Number	141-43-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16000 ;
ChEMBL	ChEMBL104943 ;
ChemSpider	13835336 ;
DrugBank	DB03994 ;
ECHA InfoCard	100.004.986
EC Number	205-483-3;
KEGG	D05074 ;
PubChem CID	700;
RTECS number	KJ5775000;
UNII	5KV86114PT ;
CompTox Dashboard (EPA)	DTXSID6022000 ;
	InChI InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYSA-N ; InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYAD;
	SMILES C(CO)N;
Properties
Chemical formula	C2H7NO
Molar mass	61.084 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)
Acidity (pKa)	9.50
Refractive index (nD)	1.4539 (20 °C)
Hazards
	GHS labelling:
Pictograms	class="wikitable collapsible" style="min-width: 50em;"

See also

{{H-phrases}}
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‹The template Category link is being considered for merging.› Category:GHS templates

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Signal word

| Danger

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Hazard statements

| H302, H312, H314, H332, H335, H412^[5]

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Precautionary statements

| P261, P273, P303+P361+P353, P305+P351+P338^[5]

|- | NFPA 704 (fire diamond)

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3

2

0

|- | Flash point | 85 °C (185 °F; 358 K) (closed cup)

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Autoignition
temperature

| 410 °C (770 °F; 683 K)

|- | Explosive limits | 5.5–17% |-

| colspan=2 style="text-align:left; background-color:#eaeaea;" | Lethal dose or concentration (LD, LC): |-

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LD₅₀ (median dose)

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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)^[8]

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|- | colspan=2 style="text-align:left; background-color:#eaeaea;" | NIOSH (US health exposure limits): |-

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PEL (Permissible)

| TWA: 3 ppm (6 mg/m³)^[7]

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REL (Recommended)

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TWA: 3 ppm (8 mg/m³)
ST: 6 ppm (15 mg/m³)^[7]

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IDLH (Immediate danger)

| 30 ppm^[7]

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Related compounds

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

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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 to that of ammonia.^[9] 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.^[10]

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.^[11]

Biochemistry

Ethanolamine is biosynthesized by decarboxylation of serine:^[12]

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.^[13]

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, chemical intermediates.^[9]

For example, reacting ethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent, EDTA.^[11]

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 H₂S from various gas streams; e.g., flue gas and sour natural gas.^[14]. 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. ^[11]^[15]

Other uses

In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.^[16]

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

^ ^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. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
^ 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.
^ ^a ^b ^c Sigma-Aldrich Co., Ethanolamine. Retrieved on 2018-05-24.
^ ^a ^b "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).
^ ^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).
^ ^a ^b "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a10_001. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)
^ Cough, Cold, and Allergy Preparation Toxicity at eMedicine
^ ^a ^b ^c 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

Template:Amino alcohols

[iupac2013-1] 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'.

[2] "Ethanolamine MSDS" (PDF). Acros Organics. Archived from the original (PDF) on 2011-07-15. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)

[3] Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.

[4] 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.

[sigma-5] Sigma-Aldrich Co., Ethanolamine. Retrieved on 2018-05-24.

[GHS2021_annex-3-6] "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).

[NIOSH-7] NIOSH Pocket Guide to Chemical Hazards. "#0256". National Institute for Occupational Safety and Health (NIOSH).

[8] "Ethanolamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-9] "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a10_001. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)

[10] Cough, Cold, and Allergy Preparation Toxicity at eMedicine

[weissermel-11] 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.

[12] ttp://lipidlibrary.aocs.org/Lipids/pe/index.htm

[13] 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.

[14] ttp://www.nap.edu/openbook.php?record_id=11170^{[full citation needed]}

[15] "Ethanolamine". Occupational Safety & Health Administration.

[Carrasco-16] Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes Cosméticos 4ª Ed. www.imagenpersonal.net. p. 306. ISBN 978-84-613-4979-1.

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Names


Preferred IUPAC name 2-Aminoethan-1-ol^[1]
Other names 2-Aminoethanol 2-Amino-1-ethanol Ethanolamine (not recommended^[1]) Monoethanolamine β-Aminoethanol β-hydroxyethylamine β-Aminoethyl alcohol Glycinol Olamine MEA Ethylolamine 2-Hydroxyethylamine Colamine
Identifiers
CAS Number	141-43-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16000^Y
ChEMBL	ChEMBL104943^Y
ChemSpider	13835336^Y
DrugBank	DB03994^Y
ECHA InfoCard	100.004.986
EC Number	205-483-3
KEGG	D05074^Y
PubChem CID	700
RTECS number	KJ5775000
UNII	5KV86114PT^Y
CompTox Dashboard (EPA)	DTXSID6022000
InChI InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2^Y Key: HZAXFHJVJLSVMW-UHFFFAOYSA-N^Y InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYAD
SMILES C(CO)N
Properties
Chemical formula	C₂H₇NO
Molar mass	61.084 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 (pK_a)	9.50^[3]
Refractive index (n_D)	1.4539 (20 °C)^[4]
Hazards
GHS labelling:
Pictograms	class="wikitable collapsible" style="min-width: 50em;"
Pictogram	Code	Symbol description	Image link
	GHS01	{{GHS exploding bomb}}	Image:GHS-pictogram-explos.svg	Explosive
	GHS02	{{GHS flame}}	Image:GHS-pictogram-flamme.svg
	GHS03	{{GHS flame over circle}}	Image:GHS-pictogram-rondflam.svg
	GHS04	{{GHS gas cylinder}}	Image:GHS-pictogram-bottle.svg
	GHS05	{{GHS corrosion}}	Image:GHS-pictogram-acid.svg	Corrosive
	GHS06	{{GHS skull and crossbones}}	Image:GHS-pictogram-skull.svg	Accute Toxic
	GHS07	{{GHS exclamation mark}}	Image:GHS-pictogram-exclam.svg	Irritant
	GHS08	{{GHS health hazard}}	Image:GHS-pictogram-silhouette.svg	Health Hazard
	GHS09	{{GHS environment}}	Image:GHS-pictogram-pollu.svg	Environment

Code	Symbol description	Image link
GHS01	{{GHS exploding bomb}}	Image:GHS-pictogram-explos.svg	Explosive
GHS02	{{GHS flame}}	Image:GHS-pictogram-flamme.svg
GHS03	{{GHS flame over circle}}	Image:GHS-pictogram-rondflam.svg
GHS04	{{GHS gas cylinder}}	Image:GHS-pictogram-bottle.svg
GHS05	{{GHS corrosion}}	Image:GHS-pictogram-acid.svg	Corrosive
GHS06	{{GHS skull and crossbones}}	Image:GHS-pictogram-skull.svg	Accute Toxic
GHS07	{{GHS exclamation mark}}	Image:GHS-pictogram-exclam.svg	Irritant
GHS08	{{GHS health hazard}}	Image:GHS-pictogram-silhouette.svg	Health Hazard
GHS09	{{GHS environment}}	Image:GHS-pictogram-pollu.svg	Environment