Difference between revisions of "Tert-Butanol"
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| MeltingPt_ref = | | MeltingPt_ref = | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| − | | Odor = | + | | Odor = Camphor-like |
| pKa = 16.54 | | pKa = 16.54 | ||
| pKb = | | pKb = | ||
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| ExternalMSDS = [http://www.sciencelab.com/msds.php?msdsId=9923195 ScienceLab] | | ExternalMSDS = [http://www.sciencelab.com/msds.php?msdsId=9923195 ScienceLab] | ||
| FlashPt = 11 °C | | FlashPt = 11 °C | ||
| − | | LD50 = | + | | LD50 = 3,559 mg/kg (rabbit, oral)<br>3,500 mg/kg (rat, oral) |
| LC50 = | | LC50 = | ||
| MainHazards = Irritant | | MainHazards = Irritant | ||
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| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = [[Butanol]]<br>[[sec-Butanol]]<br>[[Isobutanol]] | + | | OtherCompounds = [[Butanol]]<br>[[sec-Butanol]]<br>[[Isobutanol]]<br>[[tert-Amyl alcohol]] |
}} | }} | ||
}} | }} | ||
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==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | Being a tertiary alcohol, tert-butanol cannot be oxidized to an aldehyde or ketone. | + | Being a tertiary alcohol, tert-butanol cannot be oxidized to an [[aldehyde]] or [[ketone]], like primary or secondary alcohols can. |
===Physical=== | ===Physical=== | ||
| Line 124: | Line 124: | ||
It can also be found as fuel additive, though the percentage is small. | 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== | ==Preparation== | ||
| − | tert-Butanol can be made via acid catalyzed hydrolysis of methyl tert-butyl ether. | + | 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. |
| − | + | It can also be produced by reacting very dry [[acetone]] with methylmagnesium halide (a [[Grignard reagent]]) or [[methyllithium]] (an [[organolithium reagent]]). | |
==Projects== | ==Projects== | ||
*Make [[methyl tert-butyl ether]] | *Make [[methyl tert-butyl ether]] | ||
| − | *Make potassium tert-butoxide | + | *Make [[potassium tert-butoxide]] |
==Handling== | ==Handling== | ||
===Safety=== | ===Safety=== | ||
| − | ''tert''-Butanol poses low toxicity, though it can be irritant. It is also flammable. | + | ''tert''-Butanol poses low toxicity, though it can be irritant. It is also flammable. Tert-butanol is poorly absorbed through skin, but rapidly absorbed in the organism if inhaled or ingested. Toxicity of single doses is usually low but high doses will produce a sedative or anesthetic effect. |
===Storage=== | ===Storage=== | ||
Latest revision as of 19:08, 3 November 2023
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|
| 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 |
| |
| Properties | |
| (CH3)3COH C4H10O | |
| Molar mass | 74.12 g/mol |
| Appearance | Colorless solid (<25 °C) or liquid (>25 °C) |
| Odor | Camphor-like |
| 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, isopropanol 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)
|
3,559 mg/kg (rabbit, oral) 3,500 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.
Contents
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.
It can also be produced by reacting very dry acetone with methylmagnesium halide (a Grignard reagent) or methyllithium (an organolithium reagent).
Projects
Handling
Safety
tert-Butanol poses low toxicity, though it can be irritant. It is also flammable. Tert-butanol is poorly absorbed through skin, but rapidly absorbed in the organism if inhaled or ingested. Toxicity of single doses is usually low but high doses will produce a sedative or anesthetic effect.
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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