Dibutyl ether

Dibutyl ether
Names
Preferred IUPAC name
1-Butoxybutane
Other names
  • Di-n-butyl ether
  • Butyl ether
  • n-Butyl ether
Identifiers
CAS Number
  • 142-96-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8569
ECHA InfoCard 100.005.069 Edit this at Wikidata
PubChem CID
  • 8909
UNII
  • PBM2R52P5G checkY
CompTox Dashboard (EPA)
  • DTXSID1022007 Edit this at Wikidata
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
  • CCCCOCCCC
Properties
Chemical formula
 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]
Solubility in water
 0.3 g/L[1]
Refractive index (nD)
 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
 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
Chemical compound

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. 1.8M 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.[citation needed]

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