Dipropyl ether is the symmetrical

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be ...

of two ''n''-

propyl In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often ...

groups. It is a colorless,

flammable liquid A flammable liquid is a liquid which can be easily ignited in air at ambient temperatures, i.e. it has a flash point at or below nominal threshold temperatures defined by a number of national and international standards organisations. The Occupat ...

with a sweet odor typical of ethers.

Preparation

Acid catalyzed ether synthesis

Dipropyl ether can be synthesized by reacting two molecules of ''n''-propanol in the presence of

p-toluenesulfonic acid ''p''-Toluenesulfonic acid (PTSA or ''p''TsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3 C6H4 SO3H. It is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents. The CH3C ...

(a strong acid) and heat, in the same way other symmetrical ethers may be formed.

Williamson ether synthesis

This ether may also be prepared by way of the

Williamson ether synthesis The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide io ...

in which ''n''-propoxide, the conjugate base of ''n''-propanol, is reacted with an ''n''-propyl halide: : Williamson ether synthesis of dipropyl ether

Safety

As is typical of ethers, dipropyl ether may slowly form explosive organic peroxides over long periods in storage. Antioxidants such as

butylated hydroxytoluene Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidat ...

are often added to ethers to prevent this process. 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.

References

{{reflist Dialkyl ethers Symmetrical ethers Sweet-smelling chemicals

Preparation

Acid catalyzed ether synthesis

Williamson ether synthesis

Safety

See also

References