Diisopropyl ether
 | |
| Names | |
|---|---|
| Preferred IUPAC name
2-[(Propan-2-yl)oxy]propane | |
| Other names
Isopropyl ether
2-Isopropoxypropane Diisopropyl oxide DIPE | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.237 |
| EC Number |
|
PubChem CID
|
|
| RTECS number |
|
| UNII | |
| UN number | 1159 |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C6H14O | |
| Molar mass | 102.177 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Sharp, sweet, ether-like[1] |
| Density | 0.725 g/ml |
| Melting point | −60 °C (−76 °F; 213 K) |
| Boiling point | 68.5 °C (155.3 °F; 341.6 K) |
| 2 g/L at 20 °C | |
| Vapor pressure | 119 mmHg (20°C)[1] |
| −79.4·10−6 cm3/mol | |
| Hazards | |
| GHS labelling: | |
  
| |
| Danger | |
| H225, H316, H319, H335, H336, H361, H371, H412 | |
| P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | −28 °C (−18 °F; 245 K) |
| 443 °C (829 °F; 716 K) | |
| Explosive limits | 1.4–7.9% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
8470 mg/kg (rat, oral)[2] |
LDLo (lowest published)
|
5000-6500 mg/kg (rabbit, oral)[2] |
LC50 (median concentration)
|
38,138 ppm (rat) 30,840 ppm (rabbit) 28,486 ppm (rabbit)[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
|
TWA 500 ppm (2100 mg/m3)[1] |
REL (Recommended)
|
TWA 500 ppm (2100 mg/m3)[1] |
IDLH (Immediate danger)
|
1400 ppm[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is also used as an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene.[3] Diisopropyl ether is sometimes represented by the abbreviation DIPE.
Use as a solvent
[edit]Whereas at 20 °C, diethyl ether will dissolve 1% by weight water, diisopropyl ether dissolves 0.88%. Diisopropyl ether is used as a specialized solvent to remove or extract polar organic compounds from aqueous solutions, e.g. phenols, ethanol, acetic acid.
In the laboratory, diisopropyl ether is useful for recrystallizations because it has a wide liquid range.[4][5] Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives.[6]
Safety
[edit]Diisopropyl ether forms explosive organic peroxides similar to TATP upon standing in air. This reaction proceeds more easily than for diethyl ether due to the increased lability of the C-H bond adjacent to oxygen. Many explosions have been known to occur during handling of old diisopropyl ether bottles.[7] Some laboratory procedures recommend use of freshly opened bottles.[4] Antioxidants such as butylated hydroxytoluene can be used to prevent this process. The stored solvent is generally tested for the presence of peroxides. It is recommended to test once every 3 months for diisopropyl ether compared to once every 12 months for diethyl ether.[8] Peroxides may be removed by stirring the ether with an aqueous solution of iron(II) sulfate (green vitriol) or sodium metabisulfite.[9][10] For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.
See also
[edit]- Dimethyl ether
- Diethyl ether
- Dipropyl ether
- Di-tert-butyl ether
- Methyl tert-butyl ether
- List of gasoline additives
References
[edit]- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0362". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c "Isopropyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ Sakuth, Michael; Mensing, Thomas; Schuler, Joachim; Heitmann, Wilhelm; Strehlke, Günther; Mayer (2010). "Ethers, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_023.pub2. ISBN 978-3-527-30673-2.
- ^ a b Andrea Goti; Francesca Cardona; Gianluca Soldaini (2005). "Methyltrioxorhenium Catalyzed Oxidation of Secondary Amines to Nitrones: N-Benzylidene-Benzylamine N-Oxide". Organic Syntheses. 81: 204. doi:10.15227/orgsyn.081.0204.
- ^ Ferenc Merényi, Martin Nilsson (1972). "2-Acetyl-1,3-Cyclopentanedione". Organic Syntheses. 52: 1. doi:10.15227/orgsyn.052.0001.
- ^ Shoji Hara, Akira Suzuk (1998). "Synthesis of 4-(2-Bromo-2-Propenyl)-4-Methyl-Y-Butyrolactone by the Reaction of Ethyl Levulinate with (2-Bromoallyl)Diisopropoxyborane Prepared by Haloboration of Allene". Organic Syntheses. 75: 129. doi:10.15227/orgsyn.075.0129.
- ^ Matyáš, Robert; Pachman, Jiří. (2013). Primary explosives. Berlin: Springer. p. 272. ISBN 978-3-642-28436-6. OCLC 832350093.
- ^ "Organic Peroxides - Hazards : OSH Answers". www.ccohs.ca. Canadian Centre for Occupational Health and Safety, Government of Canada.
- ^ Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. p. 176. ISBN 978-0-7506-7571-0.
- ^ Hamstead, A. C. (1964). "Destroying Peroxides of Isopropyl Ether". Industrial and Engineering Chemistry. 56 (6): 37-42. doi:10.1021/ie50654a005.