Isobutanol
Names | |
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Preferred IUPAC name
2-Methylpropan-1-ol | |
Other names
Isobutyl alcohol
IBA 2-Methyl-1-propanol 2-Methylpropyl alcohol Isopropylcarbinol | |
Identifiers | |
3D model (
JSmol ) |
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1730878 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.001.044 |
EC Number |
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49282 | |
KEGG | |
PubChem CID
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RTECS number
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UNII | |
UN number | 1212 |
CompTox Dashboard (EPA)
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Properties[3] | |
C4H10O | |
Molar mass | 74.122 g/mol |
Appearance | Colorless liquid |
Odor | sweet, musty[1] |
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[2] | |
log P | 0.8 |
Vapor pressure | 9 mmHg (20°C)[1] |
Refractive index (nD)
|
1.3959 |
Viscosity | 3.95 cP at 20 °C |
Hazards[3] | |
GHS labelling: | |
Danger | |
H226, H315, H318, H335, H336 | |
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 28 °C (82 °F; 301 K) |
415 °C (779 °F; 688 K) | |
Explosive limits
|
1.7–10.9% |
Lethal dose or concentration (LD, LC): | |
LDLo (lowest published)
|
3750 mg/kg (rabbit, oral) 2460 mg/kg (rat, oral)[4] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
|
TWA 100 ppm (300 mg/m3)[1] |
REL (Recommended)
|
TWA 50 ppm (150 mg/m3)[1] |
IDLH (Immediate danger) |
1600 ppm[1] |
Safety data sheet (SDS) | ICSC 0113 |
Related compounds | |
Related butanols
|
tert-Butanol
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Related compounds
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Isobutyraldehyde Isobutyric acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isobutanol (
Occurrence
Fusel alcohols including isobutanol are grain fermentation byproducts. Therefore, trace amounts of isobutanol may be present in many alcoholic beverages.
Production
Isobutanol is produced by the carbonylation of propylene. Two methods are practiced industrially, hydroformylation is more common and generates a mixture of isobutyraldehyde and butyraldehyde:
- CH3CH=CH2 + CO + H2 → CH3CH2CH2CHO
The reaction is catalyzed by cobalt or rhodium complexes. The resulting aldehydes are
Laboratory synthesis
Propanol and methanol can be reacted to produce isobutyl alcohol via Guerbet condensation.[6]
Biosynthesis of isobutanol
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. α-
- (CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2
- (CH3)2CHCHO + NADH + H+ → (CH3)2CHCH2OH + NAD+
Applications
The uses of isobutanol and 1-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.[5] Isobutanol is also a component of some biofuels.[8]
Safety and regulation
Isobutanol is one of the least
In March 2009, the Government of Canada announced a ban on isobutanol use in cosmetics.[9]
References
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0352". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Iso-butanol". ChemicalLand21.
- ^ a b Isobutanol, International Chemical Safety Card 0113, Geneva: International Programme on Chemical Safety, April 2005.
- ^ "Isobutyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ ISBN 978-3527306732..
- .
The synthesis of isobutyl alcohol from methanol (MeOH) and n-propanol (PrOH) through the Guerbet condensation has been studied [. . .] using catalytic system of copper chromite and Mg-Al mixed oxides.
- S2CID 4413113.
- S2CID 4423203.
- ^ "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).
- Environmental Health Criteria 65: Butanols: four isomers
- IPCS Health and Safety Guide 9: Isobutanol