Di-n-propyl ether: Difference between revisions
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===Acid catalyzed ether synthesis=== |
===Acid catalyzed ether synthesis=== |
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Dipropyl ether can be synthesized by reacting two molecules of [[propan-1-ol]] in the presence of [[4-methylbenezesulfonic acid]] (a strong acid) and heat, in the same way other symmetrical ethers may be formed.<ref>{{Cite book| title = Merck Index of Chemicals and Drugs, 14th ed| year = 2006| isbn=978-0-911910-00-1| editor = O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin| publisher = Merck Research Laboratories}}</ref> |
Dipropyl ether can be synthesized by reacting two molecules of [[propan-1-ol]] in the presence of [[4-methylbenezesulfonic acid]] (a strong acid) and heat, in the same way other symmetrical ethers may be formed.<ref name="merck">{{Cite book| title = Merck Index of Chemicals and Drugs, 14th ed| year = 2006| isbn=978-0-911910-00-1| editor = O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin| publisher = Merck Research Laboratories}}</ref> |
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===Williamson ether synthesis=== |
===Williamson ether synthesis=== |
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::[[File:Williamson_ether_synthesis_of_dipropyl_ether.png|600px|Williamson ether synthesis of dipropyl ether.]] |
::[[File:Williamson_ether_synthesis_of_dipropyl_ether.png|600px|Williamson ether synthesis of dipropyl ether.]] |
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==Safety== |
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As is typical of ethers, dipropyl ether may slowly form explosive [[organic peroxide|organic peroxides]] over long periods in storage.<ref name="merck" /> Antioxidants such as [[butylated hydroxytoluene]] are often added to ethers to prevent this process.<ref>[http://www.sigmaaldrich.com/catalog/product/sial/296082?lang=en®ion=US Diethyl ether product listing] – Sigma-Aldrich. Retrieved on 2012-07-03.</ref> |
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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 then may detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids.<ref>[http://www.ccohs.ca/oshanswers/chemicals/organic/organic_peroxide.html#_1_2 Organic peroxide hazards] - Canadian Centre for Occupational Health and Safety. Retrieved on 2012-07-03.</ref> |
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==See also== |
==See also== |
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Revision as of 23:44, 3 July 2012
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| Names | |
|---|---|
| IUPAC name
1-Propoxypropane
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| Other names
propyl ether
dipropyl ether di-n-propyl ether | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.518 |
PubChem CID
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CompTox Dashboard (EPA)
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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) |
| Boiling point | 90 °C (194 °F; 363 K) |
| 3 g/L (20 °C) | |
| Hazards | |
| Flash point | −18 °C (0 °F)[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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Dipropyl ether is the symmetrical ether of two n-propyl groups. It is a colorless, flammable liquid with a sickening sweet odor typical of ethers.
Preparation
Acid catalyzed ether synthesis
Dipropyl ether can be synthesized by reacting two molecules of propan-1-ol in the presence of 4-methylbenezesulfonic 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.[3]
Propoxide, the alkoxide anion of propan-1-ol, is reacted under mild heating with a suitable propane substrate featuring a good leaving group, such as a halogen atom or sulfonate ester, subsituted at the 1 position. The strongly electronegative oxygen atom of the propoxide molecule attacks the propane substrate and the leaving group is ejected, yielding dipropyl ether.
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 then may detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids.[5]
See also
References
- ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin, ed. (2006). Merck Index of Chemicals and Drugs, 14th ed. Merck Research Laboratories. ISBN 978-0-911910-00-1.
{{cite book}}: CS1 maint: multiple names: editors list (link) - ^ Fox, Marye; Whitesell, James (2004). Organic Chemistry, 3rd ed. Jones & Bartlett Publishers. ISBN 978-0763735869.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ Diethyl ether product listing – Sigma-Aldrich. Retrieved on 2012-07-03.
- ^ Organic peroxide hazards - Canadian Centre for Occupational Health and Safety. Retrieved on 2012-07-03.
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