Difference between revisions of "Methyl tert-butyl ether"
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| + | {{Chembox | ||
| + | | Name = Methyl tert-butyl ether | ||
| + | | Reference = | ||
| + | | IUPACName = 2-Methoxy-2-methylpropane | ||
| + | | PIN = | ||
| + | | SystematicName = | ||
| + | | OtherNames = Methyl t-butyl ether<br>Methyl tert-butyl ether<br>Methyl tertiary-butyl ether<br>MTBE<br>tBME<br>tert-Butyl methyl ether<br>tert-BuOMe | ||
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| + | <!-- Sections --> | ||
| + | | Section1 = {{Chembox Identifiers | ||
| + | | 3DMet = | ||
| + | | Abbreviations = | ||
| + | | SMILES = | ||
| + | }} | ||
| + | | Section2 = {{Chembox Properties | ||
| + | | AtmosphericOHRateConstant = | ||
| + | | Appearance = Colorless liquid | ||
| + | | BoilingPt = | ||
| + | | BoilingPtC = 55.2 | ||
| + | | BoilingPt_ref = | ||
| + | | BoilingPt_notes = | ||
| + | | Density = 0.7604 g/cm<sup>3</sup> (0 °C)<br>0.7526 g/cm<sup>3</sup> (10 °C)<br>0.7472 g/cm<sup>3</sup> (15 °C)<br>0.7404 g/cm<sup>3</sup> (20 °C)<br>0.7353 g/cm<sup>3</sup> (25 °C)<br>0.7317 g/cm<sup>3</sup> (30 °C)<br>0.7261 g/cm<sup>3</sup> (35 °C)<br>0.7209 g/cm<sup>3</sup> (40 °C)<br>0.7099 g/cm<sup>3</sup> (50 °C) | ||
| + | | Formula = C<sub>5</sub>H<sub>12</sub>O | ||
| + | | HenryConstant = | ||
| + | | LogP = | ||
| + | | MolarMass = 88.15 g/mol | ||
| + | | MeltingPt = | ||
| + | | MeltingPtC = −109 | ||
| + | | MeltingPt_ref = | ||
| + | | MeltingPt_notes = | ||
| + | | Odor = Terpene-like | ||
| + | | pKa = | ||
| + | | pKb = | ||
| + | | Solubility = 4.2 g/100 ml (20 °C)<br>5.1 g/100 ml (25 °C) | ||
| + | | SolubleOther = Miscible with [[acetone]], [[benzene]], [[diethyl ether]], [[ethanol]], [[ethylene glycol]], [[isobutanol]], [[isopropanol]], [[sec-Butanol|sec-butanol]], [[toluene]], [[xylene]] | ||
| + | | Solvent = | ||
| + | | VaporPressure = 250 mm Hg (25 °C) | ||
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| + | | Section4 = {{Chembox Thermochemistry | ||
| + | | DeltaGf = | ||
| + | | DeltaHc = -3,119.05 kJ/mol | ||
| + | | DeltaHf = -315.4 kJ/mol | ||
| + | | Entropy = | ||
| + | | HeatCapacity = 188.22 J·K<sup>−1</sup>·mol<sup>−1</sup> | ||
| + | }} | ||
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| + | | ShockSens = | ||
| + | | FrictionSens = | ||
| + | | DetonationV = | ||
| + | | REFactor = | ||
| + | }} | ||
| + | | Section6 = {{Chembox Hazards | ||
| + | | AutoignitionPt = 375 °C (707 °F; 648 K) | ||
| + | | ExploLimits = | ||
| + | | ExternalMSDS = [https://www.docdroid.net/i0Po283/methyl-tert-butyl-ether-sa.pdf.html Sigma-Aldrich] | ||
| + | | FlashPt = −10 °C (14 °F; 263 K) | ||
| + | | LD50 = | ||
| + | | LC50 = | ||
| + | | MainHazards = Flammable | ||
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| + | | OtherAnions = | ||
| + | | OtherCations = | ||
| + | | OtherFunction = | ||
| + | | OtherFunction_label = | ||
| + | | OtherCompounds = [[Di-tert-butyl ether]] | ||
| + | }} | ||
| + | }} | ||
'''Methyl tert-butyl ether''', also known as '''MTBE''', '''tertiary butyl methyl ether''' or '''tBME''' is an organic compound with molecular formula '''(CH<sub>3</sub>)<sub>3</sub>COCH<sub>3</sub>'''. | '''Methyl tert-butyl ether''', also known as '''MTBE''', '''tertiary butyl methyl ether''' or '''tBME''' is an organic compound with molecular formula '''(CH<sub>3</sub>)<sub>3</sub>COCH<sub>3</sub>'''. | ||
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | MTBE will react with bromine. | + | MTBE is readily hydrolysed in the presence of strong acid catalysts. |
| + | |||
| + | MTBE will react with bromine. | ||
| + | |||
| + | Unfortunately, even though it is an ether, MTBE cannot substitute [[diethyl ether]] or [[tetrahydrofuran]] in the preparation of [[Grignard reagents]]. | ||
===Physical=== | ===Physical=== | ||
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==Preparation== | ==Preparation== | ||
| − | MTBE is produced by reacting [[methanol]] with [[isobutylene]]. It can also be synthesized by reacting [[tert-butanol]] with [[methyl iodide]]. | + | MTBE is produced by reacting [[methanol]] with [[isobutylene]]. It can also be synthesized by reacting [[tert-Butanol|tert-butanol]] with [[methyl iodide]]. |
==Projects== | ==Projects== | ||
Latest revision as of 21:47, 22 July 2019
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|
| Names | |
|---|---|
| IUPAC name
2-Methoxy-2-methylpropane
| |
| Other names
Methyl t-butyl ether
Methyl tert-butyl ether Methyl tertiary-butyl ether MTBE tBME tert-Butyl methyl ether tert-BuOMe | |
| Properties | |
| C5H12O | |
| Molar mass | 88.15 g/mol |
| Appearance | Colorless liquid |
| Odor | Terpene-like |
| Density | 0.7604 g/cm3 (0 °C) 0.7526 g/cm3 (10 °C) 0.7472 g/cm3 (15 °C) 0.7404 g/cm3 (20 °C) 0.7353 g/cm3 (25 °C) 0.7317 g/cm3 (30 °C) 0.7261 g/cm3 (35 °C) 0.7209 g/cm3 (40 °C) 0.7099 g/cm3 (50 °C) |
| Melting point | −109 °C (−164 °F; 164 K) |
| Boiling point | 55.2 °C (131.4 °F; 328.3 K) |
| 4.2 g/100 ml (20 °C) 5.1 g/100 ml (25 °C) | |
| Solubility | Miscible with acetone, benzene, diethyl ether, ethanol, ethylene glycol, isobutanol, isopropanol, sec-butanol, toluene, xylene |
| Vapor pressure | 250 mm Hg (25 °C) |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
-315.4 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | −10 °C (14 °F; 263 K) |
| Related compounds | |
| Related compounds
|
Di-tert-butyl ether |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Methyl tert-butyl ether, also known as MTBE, tertiary butyl methyl ether or tBME is an organic compound with molecular formula (CH3)3COCH3.
Contents
Properties
Chemical
MTBE is readily hydrolysed in the presence of strong acid catalysts.
MTBE will react with bromine.
Unfortunately, even though it is an ether, MTBE cannot substitute diethyl ether or tetrahydrofuran in the preparation of Grignard reagents.
Physical
MTBE is a volatile, flammable, and colorless liquid, poorly soluble in water.
Availability
MTBE is available as a gasoline additive.
Preparation
MTBE is produced by reacting methanol with isobutylene. It can also be synthesized by reacting tert-butanol with methyl iodide.
Projects
- Organic extractions
- Anti-knocking agent
Handling
Safety
Unlike most ethers, MTBE has a reduced tendency to form explosive organic peroxides. Opened bottles of diethyl ether or THF can build up dangerous levels of these peroxides in months, whereas samples of MTBE are usually safe for years.
Storage
As MTBE doesn't form explosive organic peroxides, no special storage is required. Bottles containing MTBE should be kept in a cold place, away from any heat or fire source.
Disposal
MTBE can be safely burned. However, it must never dumped in the environment.
