ethanolamine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/19 05:21:12」(JST)

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Ethanolamine
IUPAC name 2-Aminoethanol
Other names 2-Amino-l-Ethanol, Ethanolamine, Monoethanolamine, β-Aminoethanol, β-hydroxyethylamine, β-Aminoethyl alcohol, Glycinol, Olamine, MEA
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)
Acidity (pKa)	9.50
Refractive index (nD)	1.4539 (20 °C)
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.

The term ethanolamines (plural) is a group of amino alcohols. A class of antihistamines is identified as ethanolamines which includes carbinoxamine, clemastine, dimenhydrinate, diphenhydramine, and doxylamine.

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.

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. For example, reacting ethanolamine with ammonia gives the commonly used chelating agent, ethylenediamine:

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

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

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English Journal

• Identification and metabolomic analysis of chemical modulators for lipid accumulation in Crypthecodinium cohnii.

• Li J1, Niu X1, Pei G1, Sui X1, Zhang X1, Chen L1, Zhang W2.
• Bioresource technology.Bioresour Technol.2015 Sep;191:362-8. doi: 10.1016/j.biortech.2015.03.068. Epub 2015 Mar 18.
• In the study, fourteen chemical modulators from five groups (i.e., auxin, gibberellin, cytokinin, signal transducer and amine) were evaluated for their effects on lipid accumulation in Crypthecodinium cohnii. The results showed that naphthoxyacetic acid (BNOA), 2-chlorodracylicacid, salicylic acid (
• PMID 25818259

• The enhancement of ammonium removal from ethanolamine wastewater using air-cathode microbial fuel cells coupled to ferric reduction.

• Shin JW1, Seo SJ1, Maitlo HA1, Park JY2.
• Bioresource technology.Bioresour Technol.2015 Aug;190:466-73. doi: 10.1016/j.biortech.2015.03.048. Epub 2015 Mar 17.
• A microbial fuel cell (MFC) with biological Fe(III) reduction was implemented for simultaneous ethanolamine (ETA) degradation and electrical energy generation. In the feasibility experiment using acetate as a substrate in a single-chamber MFC with goethite and ammonium at a ratio of 3.0(mol/mol), up
• PMID 25804534

• In Salmonella enterica, Ethanolamine Utilization Is Repressed by 1,2-Propanediol To Prevent Detrimental Mixing of Components of Two Different Bacterial Microcompartments.

• Sturms R1, Streauslin NA1, Cheng S1, Bobik TA2.
• Journal of bacteriology.J Bacteriol.2015 Jul 15;197(14):2412-21. doi: 10.1128/JB.00215-15. Epub 2015 May 11.
• Bacterial microcompartments (MCPs) are a diverse family of protein-based organelles composed of metabolic enzymes encapsulated within a protein shell. The function of bacterial MCPs is to optimize metabolic pathways by confining toxic and/or volatile metabolic intermediates. About 20% of bacteria pr
• PMID 25962913

Japanese Journal

• Synthesis and Performance Properties of Cationic Fabric Softeners Derived from Free Fatty acid of Tallow Fat

• Journal of Oleo Science advpub(0), 2016
• NAID 130005164744

• Choline Chloride Catalyzed Amidation of Fatty Acid Ester to Monoethanolamide: A Green Approach

• Journal of Oleo Science advpub(0), 2016
• NAID 130005129624

• Choline Chloride Catalyzed Amidation of Fatty Acid Ester to Monoethanolamide: A Green Approach

• Journal of Oleo Science 65(1), 75-79, 2016
• NAID 130005118528

Related Links

• Ethanolamine ≥98% | Sigma-Aldrich

Sigma-Aldrich offers Sigma-Aldrich-E9508, Ethanolamine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Attention: Maintenance Currently Underway Online ordering ...

• Ethanolamine, ReagentPlus®, ≥99% | NH2CH2CH2OH ...

Sigma-Aldrich offers Sigma-Aldrich-110167, Ethanolamine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... 411000 Ethanolamine purified by redistillation, ≥99.5% 398136 Ethanolamine

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