Ethanolamine

Source: Wikipedia, the free encyclopedia.
Ethanolamine
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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.004.986 Edit this at Wikidata
EC Number
  • 205-483-3
KEGG
RTECS number
  • KJ5775000
UNII
  • InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 checkY
    Key: HZAXFHJVJLSVMW-UHFFFAOYSA-N checkY
  • InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2
    Key: HZAXFHJVJLSVMW-UHFFFAOYAD
  • NCCO
Properties
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)
Miscible
Vapor pressure 64 Pa (20 °C)[2]
Acidity (pKa) 9.50[3]
1.4539 (20 °C)[4]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H312, H314, H332, H335, H412[5]
P261, P273, P303+P361+P353, P305+P351+P338[5]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
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):
  • 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 compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring

viscous liquid with an odor reminiscent of ammonia.[9]

Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from

antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine.[10]

Ethanolamine in Nature

ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. 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.[11]

ETA was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.[12]

Ethanolamine is biosynthesized by decarboxylation of serine:[13]

HOCH
2CH(CO
2H)NH
2 → HOCH
2CH
2NH
2 + CO2

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,[14] as well as precursor, combined with arachidonic acid C
20H
32O
2 20:4, ω-6), to form the endocannabinoid anandamide (AEA: C
22H
37NO
2; 20:4, ω-6).[15]

ETA is biodegraded by ethanolamine ammonia-lyase, a B12-dependent enzyme. It is converted to acetaldehyde and ammonia via initial H-atom abstraction.[16]

H2NCH2CH2OH → NH3 + CH3CHO

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.[17]

Applications

MEA is used as

emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.[9]

For example, reacting ethanolamine with

EDTA.[17]

Gas stream scrubbing

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

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.[17][20]

Other uses

In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.[21]

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.[22]

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
]

Reactions

Upon reaction with carbon dioxide, 2 equivalents of ethanolamine react through the intermediacy of carbonic acid to form a carbamate salt,[23] which when heated reforms ethanolamine and carbon dioxide.

References

  1. ^
    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.
  3. doi:10.1021/ja01577a030
    .
  4. doi:10.1021/ja01865a009
    .
  5. ^ a b c Sigma-Aldrich Co., Ethanolamine. Retrieved on 2018-05-24.
  6. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0256". National Institute for Occupational Safety and Health (NIOSH).
  7. ^ "Ethanolamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  8. ^ "National Library of Medicine. PubChem. Ethanolomine". NIH, National Library of Medicine. Retrieved September 5, 2021.
  9. ^
    ISBN 978-3527306732
    .
  10. ^ Cough, Cold, and Allergy Preparation Toxicity at eMedicine
  11. PMID 11426841
    .
  12. ^ "First evidence of cell membrane molecules in space". Astronomy Magazine. May 28, 2021. Retrieved September 4, 2021.
  13. ^ "Phosphatidylethanolamine and related lipids". AOCS. Archived from the original on 2012-08-21. Retrieved 2015-08-09.
  14. PMID 30190434
    .
  15. PMID 8670178
    .
  16. PMID 20519496
    .
  17. ^
    ISBN 3-527-30578-5
    .
  18. hdl:10044/1/25382
    .
  19. ISBN 978-0-309-09225-8
    .
  20. Occupational Safety & Health Administration. Archived from the original
    on 2013-05-03. Retrieved 2008-05-11.
  21. ISBN 978-84-613-4979-1
    .
  22. ^ Federal Motor Vehicle Safety Standards. U.S. Department of Transportation, National Highway Traffic Safety Administration. 1994. p. Part 571; S 108—PRE 128.
  23. doi:10.14233/ajchem.2014.15301
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Ethanolamine&oldid=1193751600"