Diphenyl ether | |
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Diphenyl ether |
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Other names
Diphenyl oxide; 1,1'-Oxybisbenzene; Phenoxybenzene |
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Identifiers | |
CAS number | 101-84-8 |
ChemSpider | 7302 |
UNII | 3O695R5M1U |
ChEBI | CHEBI:39258 |
ChEMBL | CHEMBL38934 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C12H10O |
Molar mass | 170.21 g mol−1 |
Appearance | Colorless solid or liquid with a geranium-like odor |
Melting point |
25–26 °C |
Boiling point |
121 °C at 1.34 kPa (10.05 mm Hg), 258 °C at 100 kPa (1 bar) |
Solubility in water | Insoluble |
Hazards | |
MSDS | Aldrich MSDS |
NFPA 704 |
1
2
0
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Flash point | 115 °C (388.15 K) |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Diphenyl ether is the organic compound with the formula O(C6H5)2. The molecule is subject to reactions typical of other phenyl rings, including hydroxylation, nitration, halogenation, sulfonation, and Friedel-Crafts alkylation or acylation.[1] This simple diaryl ether enjoys a variety of niche applications.
Diphenyl ether and many of its properties were first reported as early as 1901.[2] It is synthesized by a modification of the Williamson ether synthesis, here the reaction of phenol and bromobenzene in the presence of base and a catalytic amount of copper:
Involving similar reactions, diphenyl ether is a significant side product in the high-pressure hydrolysis of chlorobenzene in the production of phenol.[3]
The main application of diphenyl ether is as a eutectic mixture with biphenyl, used as a heat transfer medium. Such a mixture is well-suited for heat transfer applications because of the relatively large temperature range of its liquid state.
Diphenyl ether is a starting material in the production of phenoxathiin via the Ferrario reaction.[4] Phenoxathiin is used in polyamide and polyimide production.[5]
Because of its odor reminiscent of scented geranium, as well as its stability and low price, diphenyl ether is used widely in soap perfumes.[6] Diphenyl ether is also used as a processing aid in the production of polyesters.
Several polybrominated diphenyl ethers (PBDEs) are useful flame retardants. Of penta-, octa-, and decaBDE, the three most common PBDEs, only decaBDE is still in widespread use since its ban in the European Union in 2003.[7] DecaBDE, also known as decabromodiphenyl oxide,[8] is a high-volume industrial chemical with over 450,000 kilograms produced annually in the United States. Decabromodiphenyl oxide is sold under the trade name Saytex 102 as a flame retardant in the manufacture of paints and reinforced plastics.