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Monoethanolamine

Ethanolamine
Ethanolamine-2D-skeletal-B.png
Ethanolamine 3D spacefill.png
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
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.004.986
EC Number 205-483-3
KEGG
PubChem CID
RTECS number KJ5775000
UNII
Properties
C2H7NO
Molar mass 61.08 g·mol−1
Appearance Viscous colourless liquid
Odor unpleasant ammonia-like odour
Density 1.012 g/cm3
Melting point 10.3 °C (50.5 °F; 283.4 K)
Boiling point 170 °C (338 °F; 443 K)
Miscible
Vapor pressure 64 Pa (20 °C)
Acidity (pKa) 9.50
1.4539 (20 °C)
Hazards
Safety data sheet JT Baker
R-phrases (outdated) R20, R34, R36/37/38
S-phrases (outdated) S26, S27, S36/37, S39, S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 85 °C (185 °F; 358 K) (closed cup)
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)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 3 ppm (6 mg/m3)
REL (Recommended)
TWA 3 ppm (8 mg/m3) ST 6 ppm (15 mg/m3)
IDLH (Immediate danger)
30 ppm
Related compounds
Related compounds
N-Methylethanolamine
diethanolamine
triethanolamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Ethanolamine, also called 2-aminoethanol or monoethanolamine (often abbreviated as ETA or MEA), is an organic chemical compound with the formula HOCH2CH2NH2. The molecule is both a primary amine and a primary alcohol (due to a hydroxyl group). Ethanolamine is a colorless, viscous liquid with an odor reminiscent to that of ammonia. 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.

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.

Ethanolamine is biosynthesized by decarboxylation of serine:

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.


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Wikipedia

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