2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in 3 parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||74.123 g·mol−1|
|Density||0.808 g cm−3|
|Melting point||−115 °C; −175 °F; 158 K|
|Boiling point||98 to 100 °C; 208 to 212 °F; 371 to 373 K|
|Vapor pressure||1.67 kPa (at 20 °C)|
|Acidity (pKa)||17.6 |
|−5.7683×10−5 cm3 mol−1|
Refractive index (nD)
|1.3978 (at 20 °C)|
Heat capacity (C)
|197.1 J K−1 mol−1|
|213.1 J K−1 mol−1|
Std enthalpy of
|−343.3 to −342.1 kJ mol−1|
Std enthalpy of
|−2.6611 to −2.6601 MJ mol−1|
|Safety data sheet||inchem.org|
|GHS Signal word||Warning|
|H226, H319, H335, H336|
|NFPA 704 (fire diamond)|
|Flash point||22 to 27 °C (72 to 81 °F; 295 to 300 K)|
|405 °C (761 °F; 678 K)|
|Lethal dose or concentration (LD, LC):|
LCLo (lowest published)
|16,000 ppm (rat, 4 hr)|
10,670 ppm (mouse, 3.75 hr)
16,000 ppm (mouse, 2.67 hr)
|NIOSH (US health exposure limits):|
|TWA 150 ppm (450 mg/m3)|
|TWA 100 ppm (305 mg/m3) ST 150 ppm (455 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Manufacture and applicationsEdit
Although some 2-butanol is used as a solvent, it is mainly converted to butanone (methyl ethyl ketone, MEK), which is an important industrial solvent and found in many domestic cleaning agents and paint removers. Volatile esters of 2-butanol have pleasant aromas and are used in small amounts as perfumes or in artificial flavors.
The solubility of 2-butanol is incorrect in most sources, including some of the most well-known references such as the Merck Index, the CRC Handbook of Chemistry and Physics, and Lange's Handbook of Chemistry. Even the International Programme on Chemical Safety lists the wrong solubility. This widespread error originated because of Beilstein's Handbuch der Organischen Chemie (Handbook of Organic Chemistry). This work cites a false solubility of 12.5 g/100 g water. Many other sources used this solubility, which has snowballed into a widespread error in the industrial world. The correct data (35.0 g/100 g at 20 °C, 29 g/100 g at 25 °C, and 22 g/100 g at 30 °C) were first published in 1886 by Alexejew and then similar data was reported by other scientists including Dolgolenko and Dryer in 1907 and 1913, respectively.
Several explosions have been reported during the conventional distillation of 2-butanol, apparently due to the buildup of peroxides with the boiling point higher than that of pure alcohol (and therefore concentrating in the still pot during distillation). As alcohols, unlike ethers, are not widely known to be capable of forming peroxide impurities, the danger is likely to be overlooked. 2-Butanol is in Class B Peroxide Forming Chemicals
- "Alcohols Rule C-201.1". Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H. Oxford: Pergamon Press. 1979.
Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because there are no hydrocarbons isopropane, sec-butane, and tert-butane to which the suffix "-ol" can be added; such names should be abandoned. Isopropyl alcohol, sec-butyl alcohol, and tert-butyl alcohol are, however, permissible (see Rule C-201.3) because the radicals isopropyl, sec-butyl, and tert-butyl do exist.
- "2-butanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 12 October 2011.
- Alger, Donald B. (November 1991). "The water solubility of 2-butanol: A widespread error". Journal of Chemical Education. 68 (11): 939. doi:10.1021/ed068p939.1.
- Serjeant, E.P., Dempsey B.; Ionisation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry (IUPAC). IUPAC Chemical Data Series No. 23, 1979. New York, New York: Pergamon Press, Inc., p. 989
- NIOSH Pocket Guide to Chemical Hazards. "#0077". National Institute for Occupational Safety and Health (NIOSH).
- Hahn, Heinz-Dieter; Dämbkes, Georg; Rupprich, Norbert (2005). "Butanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH..
- Doyle, R. R. (1986). "2-Butanol safety warning". Journal of Chemical Education. 63 (2): 186. doi:10.1021/ed063p186.2.
- Peterson, Donald (11 May 1981). "Letters: Explosion of 2-butanol". Chemical & Engineering News. 59 (19): 3. doi:10.1021/cen-v059n019.p002.
- Watkins, Kenneth W. (May 1984). "Demonstration hazard". Journal of Chemical Education. 61 (5): 476. doi:10.1021/ed061p476.3.
- "Classification List of Peroxide Forming Chemicals". ehs.ucsc.edu.