Diphenyl ether

Chemical compound From Wikipedia, the free encyclopedia

Diphenyl ether

Diphenyl ether is the organic compound with the formula (C6H5)2O. It is a colorless, low-melting solid. This, the simplest diaryl ether, has a variety of niche applications.[5]

Quick Facts Names, Identifiers ...
Diphenyl ether
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Names
Preferred IUPAC name
1,1′-Oxydibenzene[1]
Systematic IUPAC name
Phenoxybenzene
Other names
Oxydibenzene
Diphenyl ether[1]
Diphenyl oxide
1,1′-Oxybisbenzene
Phenoxybenzene[1]
Identifiers
3D model (JSmol)
1364620
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.711
EC Number
  • 202-981-2
165477
RTECS number
  • KN8970000
UNII
UN number 3077
  • InChI=1S/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H Y
    Key: USIUVYZYUHIAEV-UHFFFAOYSA-N Y
  • InChI=1/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
    Key: USIUVYZYUHIAEV-UHFFFAOYAV
  • O(c1ccccc1)c2ccccc2
Properties
C12H10O
Molar mass 170.211 g·mol−1
Appearance Colorless solid or liquid
Odor geranium-like
Density 1.08 g/cm3 (20 °C)[2]
Melting point 25 to 26 °C (77 to 79 °F; 298 to 299 K)
Boiling point 258.55 °C (497.39 °F; 531.70 K)[3] at 100 kPa (1 bar),
121 °C at 1.34 kPa (10.05 mm Hg)
Insoluble
Vapor pressure 0.02 mmHg (25 °C)[2]
−108.1·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H317, H319, H360Fd, H400, H411
P264, P273, P280, P305+P351+P338, P337+P313, P391, P501
NFPA 704 (fire diamond)
ThumbHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
2
1
Flash point 115 °C (239 °F; 388 K)
Explosive limits 0.7%–6.0%[2]
Lethal dose or concentration (LD, LC):
3370 mg/kg (rat, oral)
4000 mg/kg (rat, oral)
4000 mg/kg (guinea pig, oral)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 ppm (7 mg/m3)[2]
REL (Recommended)
TWA 1 ppm (7 mg/m3)[2]
IDLH (Immediate danger)
100 ppm[2]
Safety data sheet (SDS) Aldrich MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 (German: Phenyloxyd) and studied some of its derivatives.[6]

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.[7]

Related compounds are prepared by Ullmann reactions.[8]

The compound undergoes reactions typical of other phenyl rings, including hydroxylation, nitration, halogenation, sulfonation, and Friedel–Crafts alkylation or acylation.[5]

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.[9][10]

Diphenyl ether is a starting material in the production of phenoxathiin via the Ferrario reaction.[11] Phenoxathiin is used in polyamide and polyimide production.[12]

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.[5]

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.[13] DecaBDE, also known as decabromodiphenyl oxide,[14] 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.

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References

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