Isobutanol
| Isobutanol | |
|---|---|
| |
| |
| IUPAC name | 2-Methylpropan-1-ol |
| Other names | Isobutyl alcohol, IBA, 2-Methylpropyl alcohol |
| Identifiers | |
| InChI | InChI=1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3 |
| InChIKey | ZXEKIIBDNHEJCQ-UHFFFAOYAQ |
| Standard InChI | InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3 |
| Standard InChIKey | ZXEKIIBDNHEJCQ-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| RTECS | NP9625000 |
| ChemSpider | |
| SMILES | |
| Properties[1] | |
| Chemical formula | C4H10O |
| Molar mass | 74.122 g/mol |
| Appearance | colorless liquid |
| Density | 0.802 g/cm3, liquid |
| Melting point |
-108 °C (165 K) |
| Boiling point |
108 °C (381 K) |
| Solubility in water | limited solubility |
| log P | 0.8 |
| Refractive index (nD) | 1.3959 |
| Viscosity | 3.95 cP at 20 ºC |
| Hazards[1][2][3] | |
| Material safety data sheet (MSDS) | ICSC |
| EU index number | 603-108-00-1 |
| GHS pictograms |   
|
| GHS signal word | DANGER |
| GHS hazard statements | H226, H335, H315, H318, H336 |
| Flash point | 28 °C (82 ºF) |
| Autoignition temp. | 415 ºC (779 ºF) |
| Explosive limits | 1.7–10.9% |
| PEL (U.S.) | 100 ppm TWA |
| IDLH level | 1600 ppm |
| Related compounds | |
| Other butanols | Butan-1-ol Butan-2-ol 2-Methylpropan-2-ol |
| Other compounds | Isobutyraldehyde Isobutyric acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol; also known as 2-methylpropyl alcohol, among other names) is a colorless, flammable, organic compound with a characteristic smell. Its isomers are n-butanol, 2-butanol, and tert-butanol. It is classified as an alcohol, and, as such, it is widely used as a solvent in chemical reactions, as well as being a useful starting material for organic synthesis.
Isobutanol is produced naturally during the fermentation of carbohydrates. It may also be a by-product of the decay process of organic matter.
Applications
- feedstock in the manufacture of isobutyl acetate, which is used in the production of lacquer and similar coatings, and in the food industry as a flavouring agent
- in the industrial synthesis of derivative esters; isobutyl esters such as diisobutyl phthalate (DIBP) are used as plasticizer agents in plastics, rubbers, and other dispersions
- as paint solvent
- as varnish remover
- as ink
- as paint additive, to reduce viscosity
- as paint additive, to improve brush flow
- as paint additive, to retard the formation of oil residues (blush) on painted surfaces
- as gasoline additive, to reduce carburetor icing
- as additive to automotive polish
- as additive to automotive paint cleaner
- as a chemical extractant in production of organic compounds
- as a mobile phase in thin layer chromatography.
Isobutanol could possibly serve as an alternative to gasoline to fuel combustion engines, and it is being studied by companies such as Gevo for this use.[4]
Safety
Isobutanol is a volatile, flammable liquid that should be stored and used in well-ventilated areas. It is moderately irritating to the skin and greatly irritating to the eyes, mucous membranes, and respiratory tract. Exposure to high concentrations of its vapour can cause temporary narcosis.
Isobutanol is considered to be slightly toxic and it has been shown to cause liver damage in mice and humans. Ingestion may also lead to alcohol poisoning.
In March 2009 the Canadian government announced its ban of isobutanol in cosmetics.[5]
References
- ↑ 1.0 1.1 Isobutanol; International Chemical Safety Card 0113; International Labour Organization: Geneva, April 2005, <http://www.inchem.org/documents/icsc/icsc/eics0113.htm>.
- ↑ Index no. 603-108-00-1 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 493.
- ↑ Isobutyl alcohol. In Pocket Guide to Chemical Hazards; U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149; Government Printing Office: Washington, DC, 2005. ISBN 9780160727511, <http://www.cdc.gov/niosh/npg/default.html>.
- ↑ Pentland, William Beyond Ethanol; Forbes, 2008-03-20, <http://www.forbes.com/2008/03/19/innovation-ethanol-fuel-tech-innovation08-cx_wp_0319innovation.html>. (accessed 31 August 2009).
- ↑ Cosmetic Chemicals Banned in Canada. Chem. Eng. News 2009-03-16, 87 (11), 38.
Further reading
- Pentland, William Beyond Ethanol, <http://www.forbes.com/2008/03/19/innovation-ethanol-fuel-tech-innovation08-cx_wp_0319innovation.html> (accessed 31 August 2009), Forbes; .
External links
 |
Public domain and freely licensed images and media can be found in the corresponding category on Wikimedia Commons. |
- International Chemical Safety Card 0113
- NIOSH Pocket Guide to Chemical Hazards 0352
- IPCS Environmental Health Criteria 65: Butanols: four isomers
- IPCS Health and Safety Guide 9: Isobutanol
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