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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1731254
ChemSpider	7080 ;
ECHA InfoCard	100.002.384
EC Number	202-621-4;
PubChem CID	7358;
RTECS number	EL3850000;
UNII	28002VFS3H ;
UN number	2275
CompTox Dashboard (EPA)	DTXSID2041416 ;
	InChI InChI=1S/C6H14O/c1-3-6(4-2)5-7/h6-7H,3-5H2,1-2H3 Key: TZYRSLHNPKPEFV-UHFFFAOYSA-N ;
	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). verify (what is ?) 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.

References

^ 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
^ 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.
^ 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

[hand-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

[prox-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.

[encyc-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

[1]

[2]

[3]

Reactions

Properties and applications

See also

References