Dibutyl ether

Dibutyl ether
Names

Preferred IUPAC name 1-Butoxybutane
Other names Dibutyl ether
Identifiers
CAS Number	142-96-1
3D model (Jmol)	Interactive image
ChemSpider	8569
ECHA InfoCard	100.005.069
PubChem	8909
InChI InChI=1S/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 Key: DURPTKYDGMDSBL-UHFFFAOYSA-N InChI=1/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 Key: DURPTKYDGMDSBL-UHFFFAOYAH
SMILES CCCCOCCCC
Properties
Chemical formula	C₈H₁₈O
Molar mass	130.23 g·mol⁻¹
Appearance	colorless
Density	0.769 g/cm³, liquid
Melting point	−97.9 °C (−144.2 °F; 175.2 K)
Boiling point	142.4 °C (288.3 °F; 415.5 K)
Solubility in water	0.03%
Refractive index (n_D)	1.3992
Viscosity	0.741 cP (15 °C)
Structure
Dipole moment	1.18 D
Hazards
Flash point	25 °C (77 °F; 298 K)
Autoignition temperature	194 °C (381 °F; 467 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dibutyl ether is a chemical compound belonging to the ether family with the molecular formula of C
8H
18O. 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 and many other organic solvents. Due to this property, dibutyl ether is used as solvent in various chemical reactions and processes. For example, phenyllithium is commercially available as a ca. 1.8 M 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 with sulfuric acid as a catalyst and dehydrating agent:

2C
4H
9OH → C
8H
18O + H
2O

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 for Grignard syntheses
Solvent for fats, oils, organic acids, alkaloids, natural and synthetic resins
For manufacturing of pesticides (e.g. Cyhexatin)

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