Isobutanol
| Isobutanol | |
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IUPAC name
2-methyl-1-propanol |
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Other names
Isobutyl alcohol, IBA, 2-methylpropyl alcohol |
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| Identifiers | |
| CAS number | 78-83-1  |
| PubChem | 6560 |
| ChemSpider | 6312 |
| UNII | 56F9Z98TEM |
| EC-number | 201-148-0 |
| KEGG | C14710 |
| ChEBI | CHEBI:46645 |
| ChEMBL | CHEMBL269630 |
| RTECS number | NP9625000 |
| Jmol-3D images | Image 1 |
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SMILES
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InChI
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| Properties2 | |
| Molecular formula | C4H10O |
| Molar mass | 74.122 g/mol |
| Appearance | Colorless liquid |
| Density | 0.802 g/cm3, liquid |
| Melting point |
-101.9 °C, 171 K, -151 °F |
| Boiling point |
107.89 °C, 381 K, 226 °F |
| Solubility in water | 8.7 mL/100 mL1 |
| log P | 0.8 |
| Refractive index (nD) | 1.3959 |
| Viscosity | 3.95 cP at 20 °C |
| Hazards2 | |
| MSDS | ICSC 0113 |
| EU Index | 603-108-00-1 |
| EU classification | Irritant (Xi) |
| R-phrases | R10 R37/38 R41, R67 |
| S-phrases | (S2) S7/9 S13 S26 S37/39 S46 |
| NFPA 704 |
 3
1
0
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| Flash point | 28 °C (82 °F) |
| Autoignition temperature |
415 °C (779 °F) |
| Explosive limits | 1.7–10.9% |
| Related compounds | |
| Related butanols | n-Butanol sec-Butanol tert-Butanol |
| Related compounds | Isobutyraldehyde Isobutyric acid |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Isobutanol (IUPAC nomenclature: 2-methyl-1-propanol) is an organic compound with the formula (CH3)2CHCH2OH. This colorless, flammable liquid with a characteristic smell is mainly used as a solvent. Its isomers include n-butanol, 2-butanol, and tert-butanol, all of which are more important industrially.
Contents
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Production
Isobutanol is produced by the carbonylation of propylene. Two methods are practiced industrially, hydroformylation is more common and generates a mixture of normal and isobutyraldehydes, which are hydrogenated to the alcohols and then separated. Reppe carbonylation is also practiced.3
Isobutanol is also produced naturally during the fermentation of carbohydrates and may also be a byproduct of the decay process of organic matter.citation needed Isobutanol, along with other low molecular weight alcohols can also be produced by some engineered microorganisms such as corynebacterium.4 A genetically engineered strain of the bacterium Clostridium cellulolyticum converted cellulose to isobutanol via isobutyraldehyde.5
Applications
Isobutanol has a variety of technical and industrial 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
- precursor of derivative esters; isobutyl esters such as diisobutyl phthalate (DIBP) are used as plasticizer agents in plastics, rubbers, and other dispersions
- paint solvent
- varnish remover
- ink ingredient
- paint additive, to reduce viscosity, improve brush flow, and retard formation of oil residues (blush) on painted surfaces
- gasoline additive, to reduce carburetor icing
- automotive polish additive
- automotive paint cleaner additive
- chemical extractant in production of organic compounds
- mobile phase in thin layer chromatography.
Isobutanol could possibly serve as an alternative to gasoline to fuel combustion engines, and it is being produced by companies such as Gevo.6 A 1993 SAE technical paper addresses blending methanol, ethanol and isobutanol with unleaded gasoline for use as a motor fuel.7 A similar mixture is being used by Dyson Racing in the 2010 American LeMans Series.8 Gevo acquired Agri-Energy's Luverne, Minnesota, ethanol production facility to retrofit it to produce commercial quantities of isobutanol for motor fuel.9
Safety and regulation
Isobutanol is one of the least toxic of the butanols with an LD50 of 2460 mg/kg (rat, oral).
In March 2009, the Canadian government announced a ban on isobutanol use in cosmetics.10
References
- ^ "Iso-butanol". ChemicalLand21. http://www.chemicalland21.com/petrochemical/ISO-BUTANOL.htm.
- ^ a b Isobutanol, International Chemical Safety Card 0113, Geneva: International Programme on Chemical Safety, April 2005, http://www.inchem.org/documents/icsc/icsc/eics0113.htm.
- ^ Hahn, Heinz-Dieter; Dämbkes, Georg; Rupprich, Norbert (2005), "Butanols", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a04_463.
- ^ Smith, Kevin Michael; Cho, Kwang-Myung; Liao, James C. (2010), "Engineering Corynebacterium glutamicum for isobutanol production", Applied Microbiology and Biotechnology 87 (3): 1045–1055, doi:10.1007/s00253-010-2522-6, PMC 2886118, PMID 20376637.
- ^ Shota Atsumi, Wendy Higashide, James C Liao "Direct photosynthetic recycling of carbon dioxide to isobutyraldehyde" Nature Biotechnology 27, 1177 - 1180 (2009).doi:10.1038/nbt.1586
- ^ Pentland, William (2008-03-20), Beyond Ethanol, Forbes, http://www.forbes.com/2008/03/19/innovation-ethanol-fuel-tech-innovation08-cx_wp_0319innovation.html, retrieved 2009-08-31.
- ^ sae.org/technical/papers/932953
- ^ www.dysonracing.com/company/news/article.php?news_id=1112
- ^ Wald, Matthew L. (10 March 2011). "Ethanol Plant Is Switching to Butanol". New York Times. http://green.blogs.nytimes.com/2011/03/10/ethanol-plant-is-switching-to-butanol/?hp. Retrieved 10 March 2011.
- ^ "Cosmetic Chemicals Banned in Canada", Chem. Eng. News 87 (11): 38, 2009-03-16.
External links
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Wikimedia Commons has media related to: Isobutanol |
- 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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