Ethanolamine

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 organic chemical compound with the formula HOCH
2CH
2NH
2 or C
2H
7NO.[8] The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.[9]

Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEOA). The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine.[10]

  1. ^ 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'.
  2. ^ "Ethanolamine MSDS" (PDF). Acros Organics. Archived from the original (PDF) on 2011-07-15.
  3. ^ Hall, H.K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–4. doi:10.1021/ja01577a030.
  4. ^ Reitmeier, R.E.; Sivertz, V.; Tartar, H.V. (1940). "Some Properties of Monoethanolamine and its Aqueous Solutions". Journal of the American Chemical Society. 62 (8): 1943–44. 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. ^ Martin Ernst; Johann-Peter Melder; Franz Ingo Berger; Christian Koch (2022). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.pub2. ISBN 978-3527306732.
  10. ^ Cough, Cold, and Allergy Preparation Toxicity at eMedicine