sec-Butanol

sec-Butanol

sec-Butanol bottle and sample
Names
IUPAC name Butan-2-ol
Other names 2-Butanol 2-Butyl alcohol sec-Butyl alcohol
Identifiers
Jmol-3D images	Image
SMILES CCC(C)O
Properties
Chemical formula	C4H10O
Molar mass	74.12 g/mol
Appearance	Colorless liquid
Odor	Fruity, alcoholic
Density	0.8063 g/cm3 (at 20 °C)
Melting point	−115 °C (−175 °F; 158 K)
Boiling point	98 to 100 °C (208 to 212 °F; 371 to 373 K)
Solubility in water	125 g/l (at 20 °C)
Solubility	Miscible with diethyl ether, ethanol, methanol Very soluble in acetone
Vapor pressure	1.67 kPa (at 20 °C)
Thermochemistry
Std molar entropy (So298)	213.1 J·K-1mol-1
Std enthalpy of formation (ΔfHo298)	−343.3–−342.1 kJ·mol-1
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	24 °C (75.2 °F; 297 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	2.193 mg/kg (rat, oral)
Related compounds
Related compounds	Butanol Isopropanol Methyl ethyl ketone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

sec-Butanol or 2-butanol is an isomer of butanol, mainly used as a precursor to the more common methyl ethyl ketone.

Properties

Chemical

sec-Butanol can be oxidized to butanone aka methyl ethyl ketone using Jones reagent.

sec-Butanol burns in air to release carbon dioxide and water vapors.

Physical

2-Butanol is a colorless liquid, with a strong smell. It melts at −115 °C and boils at 99.5 °C, just slightly below the boiling point of water.

Availability

2-Butanol is sold by various chemical suppliers.

Preparation

Can be made by reducing butanone using a reducing agent.

Projects

• Make butanone
• Make esters

Handling

Safety

sec-Butanol is prone to forming explosive peroxide over the course of several years, so it's best to check it periodically.

Storage

sec-Butanol should be kept in closed bottles, in the solvent cabinet.

Disposal

sec-Butanol should be tested for peroxides before disposal. If peroxides are present, a reducing agent such as sodium sulfite should be added to destroy the peroxides, then tested again to see if all the peroxides have been neutralized. If no peroxides are present, it can be safely burned.

However, unless the waste sec-butanol is very old (at least several years) and wasn't stabilized with an anti-oxidant, there is little chance of building up a dangerous amount of peroxides. Nonetheless, a peroxide test is recommended for safety reasons.

References

Relevant Sciencemadness threads

• Reducing 2-butanone to 2-butanol