Diphenyl ether
| Diphenyl ether | |
|---|---|
| File:Diphenyl oxide.svg | |
| File:Diphenyl-ether-from-xtal-2004-CM-3D-ellipsoids.png | |
| Diphenyl ether | |
| Other names Diphenyl oxide; Phenyl ether; 1,1'-Oxybisbenzene; Phenoxybenzene | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 101-84-8 
|
| style="background: #F8EABA; text-align: center;" colspan="2" | 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 |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| MSDS | Aldrich MSDS |
| NFPA 704 | |
| Flash point | 115 °C (388.15 K) |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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.
Synthesis
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:
- PhONa + PhBr → PhOPh + NaBr
Involving similar reactions, diphenyl ether is a significant side product in the high-pressure hydrolysis of chlorobenzene in the production of phenol.[3]
Uses
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.
References
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ja:ジフェニルエーテル- ↑ Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D.; Paulus, W. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
- ↑ Cook, A. N. (1901). "Derivatives of Phenylether". Journal of the American Chemical Society. 23 (11): 806–813. doi:10.1021/ja02037a005.
- ↑ Fahlbusch, K.-G.; Hammerschmidt, F.-J.; Panten, J.; Pickenhagen, W.; Schatkowski, D.; Bauer, K.; Garbe, D.; Surburg, H. (2003). "Flavor and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_141.
- ↑ Suter, C. M.; Maxwell, C. E. (1943), "Phenoxthin", Org. Synth.; Coll. Vol., 2: 485 Missing or empty
|title=(help) - ↑ Mitsuru Ueoda, Tatsuo Aizawa, Yoshio Imai (1977). "Preparation and properties of polyamides and polyimides containing phenoxathiin units". Journal of Polymer Science: Polymer Chemistry Edition. 15 (11): 2739–2747. doi:10.1002/pol.1977.170151119.
- ↑ Ungnade, H. E.; Orwoll, E. F. (1955), "2-Methoxy Diphenyl Ether", Org. Synth.; Coll. Vol., 3: 566 Missing or empty
|title=(help) - ↑ DIRECTIVE 2003/11/EC of the European Parliament and of the Council
- ↑ Sutker, B. J. (2005). "Flame Retardants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_123.
