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2-Ethyl-1-butanol

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2-Ethyl-1-butanol
Structural formula of 2-Ethyl-1-butanol
Structural formula of 2-Ethyl-1-butanol
3D ball-and-stick structure of 2-ethyl-1-butanol
3D ball-and-stick structure of 2-ethyl-1-butanol
Names
Preferred IUPAC name 2-Ethylbutan-1-ol
Other names 2-Ethyl-1-butanol
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1731254
ChemSpider
ECHA InfoCard 100.002.384 Edit this at Wikidata
EC Number
  • 202-621-4
PubChem CID
RTECS number
  • EL3850000
UNII
UN number 2275
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H14O/c1-3-6(4-2)5-7/h6-7H,3-5H2,1-2H3Key: TZYRSLHNPKPEFV-UHFFFAOYSA-N
SMILES
  • CCC(CC)CO
Properties
Chemical formula C6H14O
Molar mass 102.177 g·mol
Appearance Colorless liquid
Density 830 mg mL
Melting point −114.40 °C; −173.92 °F; 158.75 K
Boiling point 145 to 151 °C; 293 to 304 °F; 418 to 424 K
Solubility in water 10 g L
Vapor pressure 206 Pa
Refractive index (nD) 1.422
Thermochemistry
Heat capacity (C) 246.65 J K mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H312
Precautionary statements P280
Flash point 58 °C (136 °F; 331 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1.85 g kg (oral, rat)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Ethyl-1-butanol (IUPAC name: 2-ethylbutan-1-ol) is an organic chemical compound. It can be used to facilitate the separation of ethanol from water, which forms an azeotrope that otherwise limits the maximum ethanol concentration.

Reactions

2-Ethyl-1-butanol is manufactured industrially by the aldol condensation of acetaldehyde and butyraldehyde, followed by hydrogenation. It may also be prepared by the Guerbet reaction.

Properties and applications

The branching in 2-ethyl-1-butanol makes it harder to crystallize due to packing disruption, which results in a very low freezing point. Esters of 2-ethyl-1-butanol are similarly effected and it therefore finds application as a feedstock in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points.

See also

References

  1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–262, 8–106, 15–20, ISBN 978-0-8493-0594-8
  2. Roddy, James W. (1981). "Distribution of ethanol-water mixtures to organic liquids". Ind. Eng. Chem. Proc. Des. Dev. 20 (1): 104–108. doi:10.1021/i200012a016.
  3. McKetta, John J.; Cunningham, William Aaron (1994), Encyclopedia of Chemical Processing and Design, vol. 47, Boca Raton, Florida: CRC Press, p. 117, ISBN 978-0-8247-2451-1, retrieved 2010-01-25
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