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Isobutanol

Names
IUPAC name 2-Methylpropan-1-ol
Other names Isobutyl alcohol, IBA, 2-methylpropyl alcohol
Identifiers
CAS Number	78-83-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:46645
ChEMBL	ChEMBL269630
ChemSpider	6312
ECHA InfoCard	100.001.044
KEGG	C14710
PubChem CID	6560
RTECS number	NP9625000
UNII	56F9Z98TEM
CompTox Dashboard (EPA)	DTXSID0021759
InChI InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3Key: ZXEKIIBDNHEJCQ-UHFFFAOYSA-N InChI=1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
SMILES CC(C)CO
Properties
Chemical formula	C4H10O
Molar mass	74.122 g/mol
Appearance	Colorless liquid
Density	0.802 g/cm, liquid
Melting point	−101.9 °C (−151.4 °F; 171.2 K)
Boiling point	107.89 °C (226.20 °F; 381.04 K)
Solubility in water	9.5 mL/100 mL
log P	0.8
Refractive index (nD)	1.3959
Viscosity	3.95 cP at 20 ºC
Hazards
NFPA 704 (fire diamond)	1 3 0
Flash point	28 °C (82 ºF)
Explosive limits	1.7–10.9%
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) 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.

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.

Isobutanol is also produced naturally during the fermentation of carbohydrates and may also be a byproduct of the decay process of organic matter. Isobutanol, along with other low molecular weight alcohols can also be produced by some engineered microorganisms such as corynebacterium.

Research done by US Department of Energy's BioEnergy Science Center (BESC) at Oak Ridge National Laboratory for the first time produced isobutanol directly from cellulose. The team led by James Liao of the University of California at Los Angeles used the process of consolidated bioprocessing where Clostridium Cellulolyticum bacteria directly converted cellulose to isobutanol.

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. A 1993 SAE technical paper addresses blending methanol, ethanol and isobutanol with unleaded gasoline for use as a motor fuel. A similar mixture is being used by Dyson Racing in the 2010 American LeMans Series. Gevo acquired Agri-Energy's Luverne, Minnesota, ethanol production facility to retrofit it to produce commercial quantities of isobutanol for motor fuel.

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.

References

1. "Iso-butanol". ChemicalLand21.
2. ^ Isobutanol, International Chemical Safety Card 0113, Geneva: International Programme on Chemical Safety, April 2005.
3. Hahn, Heinz-Dieter; Dämbkes, Georg; Rupprich, Norbert. "Butanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_463. ISBN 978-3527306732..
4. 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.{{citation}}: CS1 maint: multiple names: authors list (link)
5. "Energy Department Announces New Advance in Biofuel Technology". United States Department of Energy. March 07, 2011. Retrieved March 07, 2011. {{cite web}}: Check date values in: |accessdate= and |date= (help)
6. Wendy Higashide, Yongchao Li, Yunfeng Yang, and James C. Liao (March 04, 2011). "Metabolic Engineering Of Clostridium Cellulolyticum For Isobutanol Production From Cellulose". American Society for Microbiology. Retrieved March 07, 2011. {{cite web}}: Check date values in: |accessdate= and |date= (help)CS1 maint: multiple names: authors list (link)
7. Pentland, William (2008-03-20), Beyond Ethanol, Forbes, retrieved 2009-08-31.
8. sae.org/technical/papers/932953
9. www.dysonracing.com/company/news/article.php?news_id=1112
10. Wald, Matthew L. (10 March 2011). "Ethanol Plant Is Switching to Butanol". New York Times. Retrieved 10 March 2011.
11. "Cosmetic Chemicals Banned in Canada", Chem. Eng. News, 87 (11): 38, 2009-03-16.

External links

• International Chemical Safety Card 0113
• NIOSH Pocket Guide to Chemical Hazards. "#0352". National Institute for Occupational Safety and Health (NIOSH).
• IPCS Environmental Health Criteria 65: Butanols: four isomers
• IPCS Health and Safety Guide 9: Isobutanol

• Alcohols
• Alcohol solvents