Diphenyl ether
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox HazardsTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| Template:Longitem | 1364620 |
| ChEBI | Template:Unbulleted list |
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| EC Number | Template:Unbulleted list |
| Template:Longitem | 165477 |
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| UN number | 3077 |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | Colorless solid or liquid |
| Odor | geranium-like |
| Density | 1.08 g/cm3 (20 °C)[2] |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Vapor pressure | 0.02 mmHg (25 °C)[2] |
| Template:Longitem | −108.1·10−6 cm3/mol |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
Script error: No such module "redirect hatnote". Diphenyl ether is the organic compound with the formula (C6H5)2O. It is a colorless, low-melting solid. This compound, the simplest diaryl ether, has a variety of niche applications.[3]
Synthesis and reactions
Diphenyl ether was discovered by Heinrich Limpricht and Karl List in 1855, when they reproduced Carl Ettling's destructive distillation of copper benzoate and separated it from the low-melting oily distillate components ignored by previous researchers. They named the compound phenyl oxide (Template:Langx) and studied some of its derivatives.[4]
Now 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:
- PhOH + PhBr → PhOPh + HBr
Involving similar reactions, diphenyl ether is a significant side product in the high-pressure hydrolysis of chlorobenzene in the production of phenol.[5]
Related compounds are prepared by Ullmann reactions.[6]
The compound undergoes reactions typical of other phenyl rings, including hydroxylation, nitration, halogenation, sulfonation, and Friedel–Crafts alkylation or acylation.[3]
Uses
The main application of diphenyl ether is as a eutectic mixture with biphenyl, used as a heat transfer fluid. Such a mixture is well-suited for heat transfer applications because of the relatively large temperature range of its liquid state. A eutectic mixture (commercially, Dowtherm A) is 73.5% diphenyl ether and 26.5% biphenyl.[7][8]
Diphenyl ether is a starting material in the production of phenoxathiin via the Ferrario reaction.[9] Phenoxathiin is used in polyamide and polyimide production.[10]
Because of its odor reminiscent of scented geranium, as well as its stability and low price, diphenyl ether is used widely in soap perfumes. Diphenyl ether is also used as a processing aid in the production of polyesters.[3]
Related compounds
It is a component of important hormone T3 or triiodothyronine.
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.[11] DecaBDE, also known as decabromodiphenyl oxide,[12] 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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- ↑ Patent Appeal No. 7555 United States Court of Customs and Patent Appeals 7 April 1966 http://openjurist.org/358/f2d/750/application-of-edward-s-blake-and-william-c-hammann
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- ↑ DIRECTIVE 2003/11/EC of the European Parliament and of the Council
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