2-Ethyl-1-butanol

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2-Ethyl-1-butanol[1]
Structural formula 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
3D model (JSmol)
1731254
ChemSpider
ECHA InfoCard 100.002.384 Edit this at Wikidata
EC Number
  • 202-621-4
RTECS number
  • EL3850000
UNII
UN number 2275
  • InChI=1S/C6H14O/c1-3-6(4-2)5-7/h6-7H,3-5H2,1-2H3 checkY
    Key: TZYRSLHNPKPEFV-UHFFFAOYSA-N checkY
  • CCC(CC)CO
Properties
C6H14O
Molar mass 102.177 g·mol−1
Appearance Colorless liquid
Density 830 mg mL−1
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
10 g L−1
Vapor pressure 206 Pa
1.422
Thermochemistry
246.65 J K−1 mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H312
P280
Flash point 58 °C (136 °F; 331 K)
Lethal dose or concentration (LD, LC):
1.85 g kg−1 (oral, rat)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[2]

Reactions

2-Ethyl-1-butanol is manufactured industrially by the aldol condensation of acetaldehyde and butyraldehyde, followed by hydrogenation.[3] 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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