Dibutyl ether is a chemical compound belonging to the

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 ...

family with the molecular formula of . It is colorless, volatile, and flammable liquid and has peculiar ethereal smell. Liquid dibutyl ether is lighter than water. On the other hand, the vapor is heavier than air. It is not soluble in water, but it is soluble in

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

and many other organic solvents. Due to this property, dibutyl ether is used as solvent in various chemical reactions and processes. For example,

phenyllithium Phenyllithium or lithobenzene is an organometallic agent with the empirical formula C6H5Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic synthes ...

is commercially available as a ca. 1.8M solution in dibutyl ether. Because of the formation of peroxides, it should be protected from heat, light and air.

Synthesis

Dibutyl ether is obtained from dehydration of

1-butanol 1-Butanol, also known as butan-1-ol or ''n''-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and ''tert''-butanol. The unmodified term butanol usually refers ...

with sulfuric acid as a catalyst and dehydrating agent: :2 → + Industrially, dibutyl ether can be obtained by dehydration of 1-butanol on alumina at 300 °C.

Reactions

This compound is generally stable to oxidation, reduction, and base. Strong acids like HI and HBr can cleave this ether. In the presence of oxygen, dibutyl ether is oxidized to a peroxide or hydroperoxide.

Applications

Solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

for Grignard syntheses * Solvent for

fat In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple est ...

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...

s, organic acids,

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

s, natural and synthetic

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on n ...

s * For manufacturing of pesticides (e.g. cyhexatin)

References

{{reflist Dialkyl ethers Ether solvents Symmetrical ethers Sweet-smelling chemicals Butyl compounds