Di-n-propyl ether
Dipropyl ether is the symmetrical ether of two n-propyl groups. It is a colorless, flammable liquid with a sweet odor typical of ethers.
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| Preferred IUPAC name
1-Propoxypropane | |
| Other names
Propyl ether, di-
Dipropyl ether, normal isomer Di-n-propyl ether | |
| Identifiers | |
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| Properties | |
| C6H14O | |
| Molar mass | 102.177 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.75 g/cm3[1] |
| Melting point | −122 °C (−188 °F; 151 K)[1] |
| Boiling point | 90 °C (194 °F; 363 K)[1] |
| 3 g/L (20 °C) | |
| Hazards | |
| NFPA 704 (fire diamond) | <imagemap>
File:NFPA 704.svg|80px|alt=NFPA 704 four-colored diamond poly 150 150 300 300 150 450 0 300 Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine poly 300 0 450 150 300 300 150 150 Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline poly 450 150 600 300 450 450 300 300 Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium poly 300 300 450 450 300 600 150 450 Special hazards (white): no code desc none </imagemap> |
| Flash point | −18 °C (0 °F; 255 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
Acid catalyzed ether synthesis
Dipropyl ether can be synthesized by reacting two molecules of n-propanol in the presence of p-toluenesulfonic acid (a strong acid) and heat, in the same way other symmetrical ethers may be formed.[2]
Williamson ether synthesis
This ether may also be prepared by way of the Williamson ether synthesis in which n-propoxide, the conjugate base of n-propanol, is reacted with an n-propyl halide:[3]
Safety
As is typical of ethers, dipropyl ether may slowly form explosive organic peroxides over long periods in storage.[2] Antioxidants such as butylated hydroxytoluene are often added to ethers to prevent this process.[4]
Due to the shock and light sensitive nature of organic peroxides, dipropyl ether should never be boiled or evaporated to dryness. This concentrates peroxides that may be present, which can then detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids.[5]
See also
References
- ^ 1.0 1.1 1.2 1.3 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ 2.0 2.1 O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin, eds. (2006). Merck Index of Chemicals and Drugs (14th ed.). Merck Research Laboratories. ISBN 978-0-911910-00-1.
- ^ Fox, Marye; Whitesell, James (2004). Organic Chemistry, 3rd ed. Jones & Bartlett Publishers. ISBN 978-0763735869.
- ^ "Diethyl ether product listing". Sigma-Aldrich. Retrieved 2012-07-03.
- ^ "Organic peroxide hazards". Canadian Centre for Occupational Health and Safety. Retrieved 2012-07-03.