Dibutyl ether

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.

Dibutyl ether
Names
Preferred IUPAC name
1-Butoxybutane
Other names
  • Di-n-butyl ether
  • Butyl ether
  • n-Butyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.069
UNII
  • 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
  • CCCCOCCCC
Properties
C8H18O
Molar mass 130.231 g·mol−1
Appearance Colorless liquid[1]
Odor Fruity[1]
Density 0.77 g/cm3 (20 °C)[1]
Melting point −95 °C (−139 °F; 178 K)[1]
Boiling point 141 °C (286 °F; 414 K)[1]
0.3 g/L[1]
1.3992
Viscosity 0.741 cP (15 °C)
Structure
1.18 D
Hazards
Flash point 25 °C (77 °F; 298 K)
175 °C (347 °F; 448 K)[1]
Lethal dose or concentration (LD, LC):
7400 mg/kg (oral, rat)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. 1.8M 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 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

References
  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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