tert-Butanol

tert-Butanol

Names
IUPAC name 2-Methylpropan-2-ol
Other names 2-Methyl-2-propanol tert-Butyl alcohol t-BuOH Trimethyl carbinol TBA
Identifiers
Jmol-3D images	Image
SMILES CC(C)(C)O
Properties
Chemical formula	(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)
Solubility in water	Miscible
Solubility	Miscible with diethyl ether, ethanol, isopropanol Soluble in chloroform
Vapor pressure	4.1 kPa (at 20 °C)
Acidity (pKa)	16.54
Thermochemistry
Std molar entropy (So298)	189.5 J·K−1·mol−1
Std enthalpy of formation (ΔfHo298)	−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)	3559 mg/kg (rabbit, oral) 3500 mg/kg (rat, oral)
Related compounds
Related compounds	Butanol sec-Butanol Isobutanol tert-Amyl alcohol
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.

Properties

Chemical

Being a tertiary alcohol, tert-butanol cannot be oxidized to an aldehyde or ketone, like primary or secondary alcohols can.

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.

Minute amounts are sometimes added in rubbing alcohol as a denaturing agent, though you will need a very large amount of rubbing alcohol to extract any useful amounts of t-BuOH. Most types have around 0.5 g/L of rubbing alcohol.

Preparation

tert-Butanol can be made via acid catalyzed hydrolysis of methyl tert-butyl ether, though if a hydrohalic acid is used, the corresponding alkyl halide is formed.

A more complex way is by reacting acetone with methylmagnesium halide (a Grignard reagent).

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

• OTC tert-Butanol
• tert-Butyl Alcohol
• Making t-butanol