Ethanol

Ethanol
A bottle of ethanol
Names
Pronunciation /ˈɛθənɒl/
Preferred IUPAC name
Ethanol[1]
Other names
  • Absolute alcohol
  • Alcohol
  • Cologne spirit
  • Drinking alcohol
  • Ethylic alcohol
  • EtOH
  • Ethyl alcohol
  • Ethyl hydroxide
  • Ethylene hydrate
  • Ethylol
  • Grain alcohol
  • Hydroxyethane
  • Methylcarbinol
Identifiers
3D model (JSmol)
1718733
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.526
787
IUPHAR/BPS
KEGG
UNII
UN number UN 1170
  • InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 Y
    Key: LFQSCWFLJHTTHZ-UHFFFAOYSA-N Y
  • InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3
    Key: LFQSCWFLJHTTHZ-UHFFFAOYAB
  • OCC
Properties
C2H6O
Molar mass 46.069 g·mol−1
Appearance Colourless liquid
Odor wine-like, pungent[2]
Density 0.78945 g/cm3 (at 20 °C)[3]
Melting point −114.14 ± 0.03[3] °C (−173.45 ± 0.05 °F; 159.01 ± 0.03 K)
Boiling point 78.23 ± 0.09[3] °C (172.81 ± 0.16 °F; 351.38 ± 0.09 K)
Miscible
log P −0.18
Vapor pressure 5.95 kPa (at 20 °C)
Acidity (pKa) 15.9 (H2O), 29.8 (DMSO)[4][5]
Magnetic susceptibility (χ)
−33.60·10−6 cm3/mol
Refractive index (nD)
1.3611[3]
Viscosity 1.2 mPa·s (at 20 °C), 1.074 mPa·s (at 25 °C)[6]
1.69 D[7]
Hazards
GHS labelling:
Danger
H225, H319, H360D
P210, P233, P240, P241, P242, P305+P351+P338
NFPA 704 (fire diamond)
2
3
0
Flash point 14 °C (Absolute)[9]
Lethal dose or concentration (LD, LC):
  • 7060 mg/kg (oral, rat)
  • 3450 mg/kg (mouse)
[10]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1000 ppm (1900 mg/m3)[10]
REL (Recommended)
TWA 1000 ppm (1900 mg/m3)[10]
IDLH (Immediate danger)
3300 ppm[10]
Safety data sheet (SDS) [8]
Related compounds
Related compounds
  • Ethane
  • Methanol
Supplementary data page
Ethanol (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et is the pseudoelement symbol for ethyl. Ethanol is a volatile, flammable, colorless liquid with a pungent taste.[11][12] As a psychoactive depressant, it is the active ingredient in alcoholic beverages, and the second most consumed drug globally behind caffeine.[13]

Ethanol is naturally produced by the fermentation process of sugars by yeasts or via petrochemical processes such as ethylene hydration. Historically it was used as a general anesthetic, and has modern medical applications as an antiseptic, disinfectant, solvent for some medications, and antidote for methanol poisoning and ethylene glycol poisoning.[14][15] It is used as a chemical solvent and in the synthesis of organic compounds, and as a fuel source for lamps, stoves, and internal combustion engines. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2023, world production of ethanol fuel was 112.0 gigalitres (2.96×1010 US gallons), coming mostly from the U.S. (51%) and Brazil (26%).[16]

The term "ethanol", originates from the ethyl group coined in 1834 and was officially adopted in 1892, while "alcohol"—now referring broadly to similar compounds—originally described a powdered cosmetic and only later came to mean ethanol specifically. Ethanol occurs naturally as a byproduct of yeast metabolism in environments like overripe fruit and palm blossoms, during plant germination under anaerobic conditions, in interstellar space, in human breath, and in rare cases, is produced internally due to auto-brewery syndrome.

Ethanol has been used since ancient times as an intoxicant. Production through fermentation and distillation evolved over centuries across various cultures. Chemical identification and synthetic production began by the 19th century.

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge, UK: The Royal Society of Chemistry. 2014. p. 30. doi:10.1039/9781849733069-00001. ISBN 978-0-85404-182-4.
  2. ^ "Ethanol". PubChem. Retrieved 29 December 2022.
  3. ^ a b c d Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, Florida: CRC Press. p. 3.246. ISBN 1-4398-5511-0.
  4. ^ Ballinger P, Long FA (1960). "Acid Ionization Constants of Alcohols. II. Acidities of Some Substituted Methanols and Related Compounds1,2". Journal of the American Chemical Society. 82 (4): 795–798. Bibcode:1960JAChS..82..795B. doi:10.1021/ja01489a008. ISSN 0002-7863.
  5. ^ Arnett EM, Venkatasubramaniam KG (1983). "Thermochemical acidities in three superbase systems". J. Org. Chem. 48 (10): 1569–1578. doi:10.1021/jo00158a001.
  6. ^ Lide DR, ed. (2012). CRC Handbook of Chemistry and Physics (92 ed.). Boca Raton, FL: CRC Press/Taylor and Francis. pp. 6–232.
  7. ^ Lide DR, ed. (2008). CRC Handbook of Chemistry and Physics (89 ed.). Boca Raton, FL: CRC Press. pp. 9–55.
  8. ^ "MSDS Ethanol". Retrieved 12 January 2023.
  9. ^ "Ethanol". webwiser.nlm.nih.gov. Archived from the original on 25 June 2021. Retrieved 25 June 2021.
  10. ^ a b c d "Ethyl Alcohol". 2 November 2018. Retrieved 23 December 2023.
  11. ^ "Ethanol". PubChem. National Library of Medicine. Retrieved 28 September 2021.
  12. ^ "Ethyl Alcohol" (PDF). Hazardous Substance Fact Sheet. New Jersey Department of Health. Retrieved 28 September 2021.
  13. ^ Song, Frank; Walker, Matthew P. (8 November 2023). "Sleep, alcohol, and caffeine in financial traders". PLOS ONE. 18 (11): e0291675. Bibcode:2023PLoSO..1891675S. doi:10.1371/journal.pone.0291675. ISSN 1932-6203. PMC 10631622. PMID 37939019.
  14. ^ Powell MA (2004). "9: Wine and the vine in ancient Mesopotamia: the cuneiform evidence". In McGovern PE, Fleming SJ, Katz SH (eds.). The Origins and Ancient History of Wine. Food and Nutrition in History and Anthropology. Vol. 11 (1 ed.). Amsterdam: Taylor & Francis. pp. 96–124. ISBN 978-0-203-39283-6. ISSN 0275-5769. Retrieved 15 September 2010.
  15. ^ Schnelle, Norbert (August 1965). "Alcohol Given Intravenously for General Anesthesia". Surgical Clinics of North America. 45 (4): 1041–1049. doi:10.1016/S0039-6109(16)37650-2. PMID 14312998. Retrieved 30 December 2022.
  16. ^ "2008 World Fuel Ethanol Production". Ellisville, Missouri: Renewable Fuels Association. Retrieved 21 June 2024.