Dibutyl ether
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| Names | |
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| Preferred IUPAC name
1-Butoxybutane | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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] | |
Refractive index (nD)
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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): | |
LD50 (median dose)
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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).
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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
[edit | edit source]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
[edit | edit source]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
[edit | edit source]- Solvent for Grignard syntheses
- Solvent for fats, oils, organic acids, alkaloids, natural and synthetic resins
- For manufacturing of pesticides (e.g. cyhexatin)