Ethanolamine

Ethanolamine
IUPAC name 2-Aminoethanol
Other names 2-Amino-l-Ethanol, Ethanolamine, Monoethanolamine, β-Aminoethanol, β-hydroxyethylamine, β-Aminoethyl alcohol, Glycinol, Olamine, MEA, UN 2491
Identifiers
CAS number	141-43-5 Y
PubChem	700
ChemSpider	13835336 Y
UNII	5KV86114PT Y
EC number	205-483-3
DrugBank	DB03994
KEGG	D05074 Y
ChEBI	CHEBI:16000 Y
ChEMBL	CHEMBL104943 Y
RTECS number	KJ5775000
Jmol-3D images	Image 1
SMILES C(CO)N
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
Properties
Molecular formula	C2H7NO
Molar mass	61.08 g mol−1
Appearance	Viscous colourless liquid with ammonia odour
Density	1.012 g/cm3
Melting point	10.3 °C, 283 K, 51 °F
Boiling point	170 °C, 443 K, 338 °F
Solubility in water	Miscible
Vapor pressure	64 Pa (20 °C)[1]
Acidity (pKa)	9.50[2]
Refractive index (nD)	1.4539 (20 °C)[3]
Hazards
MSDS	JT Baker
R-phrases	R20, R34, R36/37/38
S-phrases	S26, S27, S36/37, S39, S45
NFPA 704	2 3 0
Flash point	85 °C (closed cup)
Autoignition temperature	410 °C
Explosive limits	5.5 - 17%
U.S. Permissible exposure limit (PEL)	3 ppm
Related compounds
Related compounds	N-Methylethanolamine diethanolamine triethanolamine
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ethanolamine, also called 2-aminoethanol or monoethanolamine (often abbreviated as ETA or MEA), is an organic chemical compound that is both a primary amine and a primary alcohol (due to a hydroxyl group). Like other amines, monoethanolamine acts as a weak base. Ethanolamine is a toxic, flammable, corrosive, colorless, viscous liquid with an odor similar to that of ammonia.

Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEA). Ethanolamine is the second-most-abundant head group for phospholipids, substances found in biological membranes, and is also used in messenger molecules such as palmitoylethanolamide which has an effect on CB1 receptors.^[4]

Production

Monoethanolamine is produced by reacting ethylene oxide with aqueous ammonia; the reaction also produces diethanolamine and triethanolamine. The ratio of the products can be controlled by changing the stoichiometry of the reactants.^[5]

Note that this reaction is exothermic and that controls are needed to prevent a runaway reaction.

Applications

MEA is used in aqueous solutions for scrubbing certain acidic gases. It is used as feedstock in the production of detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, chemical intermediates.^[5][6] For example, reacting ethanolamine with ammonia gives the commonly used chelating agent, ethylenediamine:^[5]

In pharmaceutical formulations, MEA is primarily used for buffering or preparation of emulsions.^{[citation needed]}

Gas stream scrubbing

See also: carbon dioxide scrubber

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) from flue gas. Aqueous solutions can weakly dissolve certain kinds of gases from a mixed gas stream. The MEA in such solutions, acting as a weak base, then neutralizes acidic compounds dissolved in the solution to turn the molecules into an ionic form, making them polar and considerably more soluble in a cold MEA solution, and thus keeping such acidic gases dissolved in this gas-scrubbing solution. Therefore, large surface area contact with such a cold scrubbing solution in a scrubber unit can selectively remove such acidic components as hydrogen sulfide (H₂S) and CO₂ from some mixed gas streams. For example, basic solutions such as aqueous MEA or aqueous potassium carbonate can neutralize H₂S into hydrosulfide ion (HS^-) or CO₂ into bicarbonate ion (HCO₃^-).

H₂S and CO₂ are only weakly acidic gases. An aqueous solution of a strong base such as sodium hydroxide (NaOH) will not readily release these gases once they have dissolved. However, MEA is rather weak base and will re-release H₂S or CO₂ when the scrubbing solution is heated. Therefore, the MEA scrubbing solution is recycled through a regeneration unit, which heats the MEA solution from the scrubber unit to release these only slightly acidic gases into a purer form and returns the regenerated MEA solution to the scrubber unit again for reuse.

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).

References

1. ^ "Ethanolamine MSDS". Acros Organics. http://www.paclp.com/content/documents/MSDS/Ethanolamine.pdf. 
2. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
3. ^ 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. 
4. ^ 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. 
5. ^ ^{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 3527305785. 
6. ^ "Ethanolamine". Occupational Safety & Health Administration. http://www.osha.gov/SLTC/healthguidelines/ethanolamine/recognition.html. 

External links

• Brief technical specification of monoethanolamine