Dipropyl ether

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Dipropyl ether
Dipropylether.png
Identifiers
CAS number 111-43-3 YesY
PubChem 8114
ChemSpider 7823
Jmol-3D images Image 1
Properties
Molecular formula C6H14O
Molar mass 102.17 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]
Solubility in water 3 g/L (20 °C)
Hazards
NFPA 704
Flammability code 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) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −18 °C (0 °F; 255 K)[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dipropyl ether is the symmetrical ether of two n-propyl groups. It is a colorless, flammable liquid with a sweet odor typical of ethers.

Preparation[edit]

Acid catalyzed ether synthesis[edit]

Dipropyl ether can be synthesized by reacting two molecules of n-propanol 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[edit]

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]

Williamson ether synthesis of dipropyl ether.

Safety[edit]

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[edit]

References[edit]

  1. ^ a b c d Record in the GESTIS Substance Database from the IFA
  2. ^ 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. 
  3. ^ Fox, Marye; Whitesell, James (2004). Organic Chemistry, 3rd ed. Jones & Bartlett Publishers. ISBN 978-0763735869. 
  4. ^ "Diethyl ether product listing". Sigma-Aldrich. Retrieved 2012-07-03. 
  5. ^ "Organic peroxide hazards". Canadian Centre for Occupational Health and Safety. Retrieved 2012-07-03.