2-Ethyl-1-butanol

2-Ethyl-1-butanol^[1]

Names
Preferred IUPAC name 2-Ethylbutan-1-ol
Other names 2-Ethyl-1-butanol
Identifiers
CAS Number	97-95-0^N
3D model (JSmol)	Interactive image
Beilstein Reference	1731254
ChemSpider	7080^Y
ECHA InfoCard	100.002.384
EC Number	202-621-4
PubChem CID	7358
RTECS number	EL3850000
UNII	28002VFS3H^Y
UN number	2275
CompTox Dashboard (EPA)	DTXSID2041416
InChI InChI=1S/C6H14O/c1-3-6(4-2)5-7/h6-7H,3-5H2,1-2H3^Y Key: TZYRSLHNPKPEFV-UHFFFAOYSA-N^Y
SMILES CCC(CC)CO
Properties
Chemical formula	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
Solubility in water	10 g L^−1
Vapor pressure	206 Pa
Refractive index (nD)	1.422
Thermochemistry
Heat capacity (C)	246.65 J K^−1 mol^−1
Hazards
GHS labelling:
Pictograms
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^−1 (oral, rat)
Related compounds
Related compounds	Isopentane 2-Methylpentane 3-Methylpentane 3-Ethylpentane 2-Methylhexane 3-Methylhexane Valnoctamide
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

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

• 2-Ethylhexanol

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