Difference between revisions of "Diisopropyl ether"
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| − | '''Diisopropyl ether''' is an organic compound, secondary ether, used as a solvent in labs. | + | {{Chembox |
| + | | Name = Diisopropyl ether | ||
| + | | Reference = | ||
| + | | IUPACName = 2-[(Propan-2-yl)oxy]propane | ||
| + | | PIN = | ||
| + | | SystematicName = | ||
| + | | OtherNames = 2-Isopropoxypropane<br>Diisopropyl oxide<br>Isopropyl ether | ||
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| + | <!-- Sections --> | ||
| + | | Section1 = {{Chembox Identifiers | ||
| + | | 3DMet = | ||
| + | | Abbreviations = | ||
| + | | SMILES = | ||
| + | }} | ||
| + | | Section2 = {{Chembox Properties | ||
| + | | AtmosphericOHRateConstant = | ||
| + | | Appearance = Colorless liquid | ||
| + | | BoilingPt = | ||
| + | | BoilingPtC = 68.5 | ||
| + | | BoilingPt_ref = | ||
| + | | BoilingPt_notes = | ||
| + | | Density = 0.725 g/cm<sup>3</sup> | ||
| + | | Formula = C<sub>6</sub>H<sub>14</sub>O | ||
| + | | HenryConstant = | ||
| + | | LogP = | ||
| + | | MolarMass = 102.18 g/mol | ||
| + | | MeltingPt = | ||
| + | | MeltingPtC = −60 | ||
| + | | MeltingPt_ref = | ||
| + | | MeltingPt_notes = | ||
| + | | Odor = Ether-like | ||
| + | | pKa = | ||
| + | | pKb = | ||
| + | | Solubility = 0.2 g/100 ml at 20 °C | ||
| + | | SolubleOther = Miscible with glacial [[acetic acid]], [[acetone]], [[chloroform]], [[diethyl ether]], [[ethanol]], [[hexane]], [[Tetrahydrofuran|THF]], [[toluene]]<br>Immiscible with [[dimethylformamide]] | ||
| + | | Solvent = | ||
| + | | VaporPressure = 119 mmHg (20 °C) | ||
| + | }} | ||
| + | | Section3 = {{Chembox Structure | ||
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| + | | Section4 = {{Chembox Thermochemistry | ||
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| + | | HeatCapacity = | ||
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| + | | Section5 = {{Chembox Explosive | ||
| + | | ShockSens = | ||
| + | | FrictionSens = | ||
| + | | DetonationV = | ||
| + | | REFactor = | ||
| + | }} | ||
| + | | Section6 = {{Chembox Hazards | ||
| + | | AutoignitionPt = 443 °C (829 °F; 716 K) | ||
| + | | ExploLimits = 1.4–7.9% | ||
| + | | ExternalMSDS = [https://www.docdroid.net/NptuXFA/diisopropyl-ether-sa.pdf.html Sigma-Aldrich] | ||
| + | | FlashPt = −28 °C (−18 °F; 245 K) | ||
| + | | LD50 = 8,470 mg/kg (rat, oral) | ||
| + | | LC50 = 38,138 ppm (rat)<br>30,840 ppm (rabbit)<br>28,486 ppm (rabbit) | ||
| + | | MainHazards = Flammable<br>Potentially explosive | ||
| + | | NFPA-F = | ||
| + | | NFPA-H = | ||
| + | | NFPA-R = | ||
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| + | }} | ||
| + | | Section7 = {{Chembox Related | ||
| + | | OtherAnions = | ||
| + | | OtherCations = | ||
| + | | OtherFunction = | ||
| + | | OtherFunction_label = | ||
| + | | OtherCompounds = [[Diethyl ether]]<br>[[Dipropyl ether]]<br>[[Dibutyl ether]] | ||
| + | }} | ||
| + | }} | ||
| + | '''Diisopropyl ether''' ('''DIPE''') is an organic compound, secondary ether, used as a solvent in labs for certain reactions. It is not as widely used as other ethers, like [[diethyl ether]], as it's more prone to forming explosive peroxides that can explode without concentration. | ||
==Properties== | ==Properties== | ||
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==Projects== | ==Projects== | ||
| − | * | + | *Solvent for organic reactions |
==Handling== | ==Handling== | ||
===Safety=== | ===Safety=== | ||
| − | Diisopropyl ether can form explosive peroxides upon | + | Diisopropyl ether can form explosive peroxides upon contact with air for long periods. This reaction proceeds more easily than for ethyl ether, due to the secondary carbon next to the oxygen atom. The stored solvent should therefore be tested every 3 months, compared to every 12 months for diethyl ether. Unlike in the case of other ethers, if the peroxide amount is high enough, diisopropyl ether may explode without concentration. Because of this phenomenon, old diisopropyl ether bottles are very dangerous. |
===Storage=== | ===Storage=== | ||
Diisopropyl ether should be stored in glass bottles, in a dry cold place, away from any heat source. As it tends to form peroxides much easier that the other ethers, BHT, para-benzylamimophenol or a copper wire should be added, to limit the formation of peroxides. | Diisopropyl ether should be stored in glass bottles, in a dry cold place, away from any heat source. As it tends to form peroxides much easier that the other ethers, BHT, para-benzylamimophenol or a copper wire should be added, to limit the formation of peroxides. | ||
| + | |||
| + | A much better way to store DIPE is to keep it in a glass joint flask, like a round bottom flask or (for better stability) a flat bottom flask, where all the oxygen has been removed and replaced with an inert gas, like argon. Pieces of sodium metal should be added to remove any traces of oxygen. The flask should be sealed with a well greased stopcock, held in place with a clamp. Keep the ether flask in a safe place. | ||
===Disposal=== | ===Disposal=== | ||
| − | Diisopropyl ether can be safely burned, | + | Diisopropyl ether can be safely burned, unless it has peroxides. If the ether tests positive for peroxides but there is no precipitate in the ether, it's possible to neutralize the dissolved peroxides. Reducing agents, like [[Iron(II) sulfate|ferrous sulfate]], [[sodium bisulfite]] or [[sodium metabisulfite|metabisulfite]] added in excess can be used to neutralize the peroxides. After neutralization, the ether should be tested again for peroxides and if none are present, it can be safely burned. |
| + | |||
| + | If it's an old bottle, which has visible peroxide in the solution, or if very old, is very likely to have peroxides on the cap, DO NOT OPEN THE BOTTLE! Moving the diisopropyl ether bottle is very dangerous, as the material has been known to detonate even when wet. The latter requires professional help. | ||
==References== | ==References== | ||
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[[Category:Liquids]] | [[Category:Liquids]] | ||
[[Category:Peroxide forming chemicals]] | [[Category:Peroxide forming chemicals]] | ||
| + | [[Category:Air-sensitive materials]] | ||
Latest revision as of 20:05, 9 November 2018
 |
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|
| Names | |
|---|---|
| IUPAC name
2-[(Propan-2-yl)oxy]propane
| |
| Other names
2-Isopropoxypropane
Diisopropyl oxide Isopropyl ether | |
| Properties | |
| C6H14O | |
| Molar mass | 102.18 g/mol |
| Appearance | Colorless liquid |
| Odor | Ether-like |
| Density | 0.725 g/cm3 |
| Melting point | −60 °C (−76 °F; 213 K) |
| Boiling point | 68.5 °C (155.3 °F; 341.6 K) |
| 0.2 g/100 ml at 20 °C | |
| Solubility | Miscible with glacial acetic acid, acetone, chloroform, diethyl ether, ethanol, hexane, THF, toluene Immiscible with dimethylformamide |
| Vapor pressure | 119 mmHg (20 °C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | −28 °C (−18 °F; 245 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
8,470 mg/kg (rat, oral) |
| LC50 (Median concentration)
|
38,138 ppm (rat) 30,840 ppm (rabbit) 28,486 ppm (rabbit) |
| Related compounds | |
| Related compounds
|
Diethyl ether Dipropyl ether Dibutyl ether |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Diisopropyl ether (DIPE) is an organic compound, secondary ether, used as a solvent in labs for certain reactions. It is not as widely used as other ethers, like diethyl ether, as it's more prone to forming explosive peroxides that can explode without concentration.
Contents
Properties
Chemical
Diisopropyl ether is highly flammable and will burn in air if ignited.
Physical
Diisopropyl ether is a colorless liquid, with a sharp sweet smell, poorly soluble in water, but miscible with many organic solvents. It boils at 68.5 °C and freezes at −60 °C.
Availability
Diisopropyl ether is difficult to acquire from chemical suppliers, due to its hazards.
Preparation
Can be prepared via acid ether synthesis of isopropanol.
Projects
- Solvent for organic reactions
Handling
Safety
Diisopropyl ether can form explosive peroxides upon contact with air for long periods. This reaction proceeds more easily than for ethyl ether, due to the secondary carbon next to the oxygen atom. The stored solvent should therefore be tested every 3 months, compared to every 12 months for diethyl ether. Unlike in the case of other ethers, if the peroxide amount is high enough, diisopropyl ether may explode without concentration. Because of this phenomenon, old diisopropyl ether bottles are very dangerous.
Storage
Diisopropyl ether should be stored in glass bottles, in a dry cold place, away from any heat source. As it tends to form peroxides much easier that the other ethers, BHT, para-benzylamimophenol or a copper wire should be added, to limit the formation of peroxides.
A much better way to store DIPE is to keep it in a glass joint flask, like a round bottom flask or (for better stability) a flat bottom flask, where all the oxygen has been removed and replaced with an inert gas, like argon. Pieces of sodium metal should be added to remove any traces of oxygen. The flask should be sealed with a well greased stopcock, held in place with a clamp. Keep the ether flask in a safe place.
Disposal
Diisopropyl ether can be safely burned, unless it has peroxides. If the ether tests positive for peroxides but there is no precipitate in the ether, it's possible to neutralize the dissolved peroxides. Reducing agents, like ferrous sulfate, sodium bisulfite or metabisulfite added in excess can be used to neutralize the peroxides. After neutralization, the ether should be tested again for peroxides and if none are present, it can be safely burned.
If it's an old bottle, which has visible peroxide in the solution, or if very old, is very likely to have peroxides on the cap, DO NOT OPEN THE BOTTLE! Moving the diisopropyl ether bottle is very dangerous, as the material has been known to detonate even when wet. The latter requires professional help.
