Tert-Butanol
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- The correct title of this article is tert-Butanol. The initial letter is shown capitalized due to technical restrictions.
| tert-Butanol[1] | |
|---|---|
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| Chemical name | 2-Methyl-2-propanol |
| Other names | t-Butanol tert-Butanol t-Butyl alcohol tert-Butyl alcohol tertiary-Butyl alcohol |
| Chemical formula | C4H10O |
| Molecular mass | 74.1216(42) g/mol |
| CAS number | [75-65-0] |
| Density | 0.78086 g/cm3 |
| Melting point | 25.69 °C |
| Boiling point | 82.4 °C |
| SMILES | C(C)(C)(C)O |
| NFPA 704 |
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| Disclaimer and references | |
tert-Butanol, or 2-methyl-2-propanol, is a tertiary alcohol. It is one of the four isomers of butanol. tert-Butanol is a clear liquid with a camphor-like odor. It is well soluble in water and miscible with ethanol and diethyl ether.
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[edit] Applications
tert-Butanol is used as a solvent, as a denaturant for ethanol, as an ingredient in paint removers, as an octane booster for gasoline, as an oxygenate gasoline additive, and as an intermediate in the synthesis of other chemical commodities such as flavors and perfumes.
[edit] Preparation
tert-Butanol can be manufactured industrially by the catalytic hydration of isobutylene.
[edit] Chemistry
As a tertiary alcohol, tert-butanol is more stable to oxidation and less reactive than the other isomers of butanol.
When tert-butanol is deprotonated with a strong base, the product is an alkoxide anion. In this case, it is tert-butoxide. For example, when tert-butanol is deprotonated with sodium hydride, the resultant is sodium tert-butoxide.
- NaH + tBuOH → tBuO−Na+ + H2
The tert-butoxide species is itself a useful as a strong, non-nucleophilic base in organic chemistry. It is able to abstract acidic protons from the substrate molecule readily, but its steric bulk prevents the group from participating in nucleophilic addition, such as in a Williamson ether synthesis or an SN2 reaction.
[edit] References
- ^ Merck Index, 11th Edition, 1542
