tert-Butanol
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Names | |
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IUPAC name
2-Methylpropan-2-ol
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Other names
2-Methyl-2-propanol
tert-Butyl alcohol t-BuOH Trimethyl carbinol TBA | |
Identifiers | |
Jmol-3D images | Image |
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Properties | |
(CH3)3COH C4H10O | |
Molar mass | 74.12 g/mol |
Appearance | Colorless solid (<25 °C) or liquid (>25 °C) |
Odor | Camphorous |
Density | 0.7886 g/cm3 (at 20 °C) |
Melting point | 25.81 °C (78.46 °F; 298.96 K) |
Boiling point | 82.3 °C (180.1 °F; 355.4 K) |
Miscible | |
Solubility | Miscible with diethyl ether, ethanol Soluble in chloroform |
Vapor pressure | 4.1 kPa (at 20 °C) |
Acidity (pKa) | 16.54 |
Thermochemistry | |
Std molar
entropy (S |
189.5 J·K−1·mol−1 |
Std enthalpy of
formation (ΔfH |
−360.04–−358.36 kJ·mol−1 |
Hazards | |
Safety data sheet | ScienceLab |
Flash point | 11 °C |
Lethal dose or concentration (LD, LC): | |
LD50 (Median dose)
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3559 mg/kg (rabbit, oral) 3500 mg/kg (rat, oral) |
Related compounds | |
Related compounds
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Butanol sec-Butanol Isobutanol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
tert-Butanol or tert-Butyl alcohol (TBA), also known as 2-methylpropan-2-ol (2M2P), is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes shortened to t-BuOH). One of the most interesting characteristics of t-BuOH is that it can be a clear liquid or a colorless solid depending on the ambient temperature and season, with a melting point around 25 °C.
Contents
Properties
Chemical
Being a tertiary alcohol, tert-butanol cannot be oxidized to an aldehyde or ketone.
Physical
tert-Butanol is a colorless solid at standard conditions, but has a very high melting point for a simple alcohol, of only 25.8 °C. It's boiling point is 82.3 °C. t-BuOH is miscible with water and has a camphor-like smell.
Availability
t-BuOH is sold by various chemical suppliers.
It can also be found as fuel additive, though the percentage is small.
Small amounts are added in rubbing alcohol as a denaturing agent.
Preparation
tert-Butanol can be made via acid catalyzed hydrolysis of methyl tert-butyl ether.
A more complex way is by reacting acetone with methylmagnesium halide
Projects
- Make methyl tert-butyl ether
- Make potassium tert-butoxide
Handling
Safety
tert-Butanol poses low toxicity, though it can be irritant. It is also flammable.
Storage
tert-Butanol should be stored in closed bottles, preferably glass. If the temperature inside the storage area drops below 25 °C, such as during cold seasons, rain or night, t-BuOH will freeze. This is not usually a problem, as it does not expand upon freezing and is also less volatile when solid, but getting it out of the bottle may become frustrating.
Disposal
tert-Butanol can be safely burned, either pure or dissolved in a more flammable solvent. It can also be destroyed with Fenton's reagent, though this is not always necessary.
References
Relevant Sciencemadness threads
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