Difference between revisions of "Tert-Amyl alcohol"
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− | '''''tert''-Amyl alcohol''' ('''TAA''') or '''2-methyl-2-butanol''', is | + | '''''tert''-Amyl alcohol''' ('''TAA''') or '''2-methyl-2-butanol''', is an isomer of [[pentanol]] and the second-smallest tertiary alcohol after the better-known [[tert-butanol]]. |
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
− | ''tert''-Amyl alcohol, like all tertiary alcohols, resists oxidation to aldehyde or carboxylic acid. | + | ''tert''-Amyl alcohol, like all tertiary alcohols, resists oxidation to an aldehyde or carboxylic acid. Due to the high stability of its cation, it is quite easy to prepare tert-amyl halides from, reacting readily with hydrogen halides at room temperature. |
===Physical=== | ===Physical=== | ||
− | ''tert''-Amyl alcohol is a colorless liquid | + | ''tert''-Amyl alcohol is a colorless liquid with a camphor-like odor. It is somewhat soluble in water, but miscible with other organic solvents, like alcohols and halocarbons. |
==Availability== | ==Availability== | ||
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==Projects== | ==Projects== | ||
*Preparation of metallic [[potassium]] and [[sodium]] | *Preparation of metallic [[potassium]] and [[sodium]] | ||
− | |||
==Handling== | ==Handling== | ||
===Safety=== | ===Safety=== | ||
− | ''tert''-Amyl alcohol is flammable and | + | ''tert''-Amyl alcohol is flammable and a skin irritant. Ingestion or inhalation produces intoxication similar in many ways to ethanol, though it is around 20 times more potent by volume and produces longer-lasting effects. Exposure to vapor in the lab or accidental ingestion may cause temporary loss of physical and mental faculties or even sedation. |
===Storage=== | ===Storage=== | ||
− | ''tert''-Amyl alcohol should be kept in closed bottles | + | ''tert''-Amyl alcohol should be kept in closed bottles made of glass or chemically resistant plastic such as HDPE, preferably in a flammables cabinet. |
===Disposal=== | ===Disposal=== |
Revision as of 12:15, 29 September 2018
Low purity forerun (left) and high purity end run (right) tert-amyl alcohol, obtained via Grignard reaction route.
| |
Names | |
---|---|
IUPAC name
2-Methylbutan-2-ol
| |
Other names
2-Methyl-2-butanol
2-Methyl-2-butyl alcohol Amylene hydrate Dimethylethylcarbinol TAA t-Amylol t-Pentylol tert-Amyl alcohol tert-Pentyl alcohol | |
Properties | |
C5H12O CH3CH2(CH3)2C(OH) | |
Molar mass | 88.15 g/mol |
Appearance | Colorless liquid |
Odor | Camphor-like |
Density | 0.8096 g/cm3 (20 °C) |
Melting point | −9 °C (16 °F; 264 K) |
Boiling point | 102.4 °C (216.3 °F; 375.5 K) |
12 g/100 ml | |
Solubility | Miscible with acetone, diethyl ether, benzene, chloroform, ethanol, glycerol, oils |
Vapor pressure | 1.6 kPa (at 20 °C) |
Thermochemistry | |
Std molar
entropy (S |
229.3 J·K−1·mol−1 |
Std enthalpy of
formation (ΔfH |
−380.0–−379.0 kJ/mol |
Hazards | |
Safety data sheet | Sigma-Aldrich |
Flash point | 19 °C (66 °F; 292 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (Median dose)
|
1,000 mg/kg (rat, oral) |
Related compounds | |
Related compounds
|
tert-Butanol Pentanol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
tert-Amyl alcohol (TAA) or 2-methyl-2-butanol, is an isomer of pentanol and the second-smallest tertiary alcohol after the better-known tert-butanol.
Contents
Properties
Chemical
tert-Amyl alcohol, like all tertiary alcohols, resists oxidation to an aldehyde or carboxylic acid. Due to the high stability of its cation, it is quite easy to prepare tert-amyl halides from, reacting readily with hydrogen halides at room temperature.
Physical
tert-Amyl alcohol is a colorless liquid with a camphor-like odor. It is somewhat soluble in water, but miscible with other organic solvents, like alcohols and halocarbons.
Availability
tert-Pentanol is sold by chemical suppliers.
Can also be extracted via fractional distillation from fusel oil.
Preparation
tert-Amyl alcohol can be prepared via the bromoethylethylmagnesium Grignard with acetone route.
NurdRage has a good video on this process.
Projects
Handling
Safety
tert-Amyl alcohol is flammable and a skin irritant. Ingestion or inhalation produces intoxication similar in many ways to ethanol, though it is around 20 times more potent by volume and produces longer-lasting effects. Exposure to vapor in the lab or accidental ingestion may cause temporary loss of physical and mental faculties or even sedation.
Storage
tert-Amyl alcohol should be kept in closed bottles made of glass or chemically resistant plastic such as HDPE, preferably in a flammables cabinet.
Disposal
Can be safely burned outside. Combustion products are not harmful.