Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers, the other butanols, include n-butanol, 2-butanol, and tert-butanol, all of which are important industrially.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||74.122 g/mol|
|Density||0.802 g/cm3, liquid|
|Melting point||−108 °C (−162 °F; 165 K)|
|Boiling point||107.89 °C (226.20 °F; 381.04 K)|
|8.7 mL/100 mL|
|Vapor pressure||9 mmHg (20°C)|
Refractive index (nD)
|Viscosity||3.95 cP at 20 °C|
|Safety data sheet||ICSC 0113|
|R-phrases (outdated)||R10 R37/38 R41, R67|
|S-phrases (outdated)||(S2) S7/9 S13 S26 S37/39 S46|
|NFPA 704 (fire diamond)|
|Flash point||28 °C (82 °F; 301 K)|
|415 °C (779 °F; 688 K)|
|Lethal dose or concentration (LD, LC):|
LDLo (lowest published)
|3750 mg/kg (rabbit, oral)|
2460 mg/kg (rat, oral)
|NIOSH (US health exposure limits):|
|TWA 100 ppm (300 mg/m3)|
|TWA 50 ppm (150 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 ?)(|
- CH3CH=CH2 + CO + H2 → CH3CH2CH2CHO
The reaction is catalyzed by cobalt or rhodium complexes. The resulting aldehyde are subsequentlyhydrogenated to the alcohols, which are then separated. In Reppe carbonylation, the same products are obtained, but the hydrogenation is effected by the water-gas shift reaction.
Biosynthesis of isobutanolEdit
E. coli as well as several other organisms has been genetically modified to produce C4 alcohols from glucose, including isobutanol, 1-butanol, 2-methyl-1-butanol, 3-methyl-1-butanol, and 2-phenylethanol. The host's highly active amino acid biosynthetic pathway is shifted to alcohol production.
The uses of isobutanol and n-butanol are similar. They are often used interchangeably. The main applications are as varnishes and precursors to esters, which are useful solvents, e.g. isobutyl acetate. Isobutyl esters of phthalic, adipic, and related dicarboxylic acids are common plasticizers. Isobutanol is also a component of some biofuels.
Safety and regulationEdit
- NIOSH Pocket Guide to Chemical Hazards. "#0352". National Institute for Occupational Safety and Health (NIOSH).
- "Iso-butanol". ChemicalLand21.
- Isobutanol, International Chemical Safety Card 0113, Geneva: International Programme on Chemical Safety, April 2005.
- "Isobutyl alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). 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. doi:10.1002/14356007.a04_463..
- Atsumi, Shota; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501.
- Peralta-Yahya, Pamela P.; Zhang, Fuzhong; del Cardayre, Stephen B.; Keasling, Jay D.; Del Cardayre, Stephen B.; Keasling, Jay D. (15 August 2012). "Microbial engineering for the production of advanced biofuels". Nature. 488 (7411): 320–328. Bibcode:2012Natur.488..320P. doi:10.1038/nature11478. PMID 22895337.CS1 maint: multiple names: authors list (link)
- "Cosmetic Chemicals Banned in Canada", Chem. Eng. News, 87 (11): 38, 2009-03-16.
|Wikimedia Commons has media related to Isobutanol.|