Diphenyl ether

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Diphenyl ether
Diphenyl oxide.svg
Diphenyl-ether-from-xtal-2004-CM-3D-ellipsoids.png
Names
Preferred IUPAC name
1,1'-Oxydibenzene[1]
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
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 121 °C (250 °F; 394 K)[3] at 1.34 kPa (10.05 mm Hg), 258.55 °C at 100 kPa (1 bar)
Insoluble
Vapor pressure 0.02 mmHg (25°C)[2]
-108.1·10−6 cm3/mol
Hazards
Safety data sheet Aldrich MSDS
GHS pictograms GHS07: HarmfulGHS09: Environmental hazard
GHS signal word Warning
H319, H400, H411
P264, P273, P280, P305+351+338, P337+313, P391, P501
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
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]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 1 ppm (7 mg/m3)[2]
REL (Recommended)
TWA 1 ppm (7 mg/m3)[2]
IDLH (Immediate danger)
100 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

Synthesis and reactions[edit]

Diphenyl ether and many of its properties were first reported as early as 1901,[6] 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.[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[edit]

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. A eutectic mixture [commercially, Dowtherm A] is 73.5% diphenyl ether (diphenyl oxide) and 26.5% biphenyl (diphenyl).[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]

Related compounds[edit]

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.

Decabromodiphenyl ether.svg

References[edit]

  1. ^ a b c "CHAPTER P-6. Applications to Specific Classes of Compounds". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 705. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0496". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Byers, Charles H.; Williams, David F. (July 1987). "Viscosities of pure polyaromatic hydrocarbons". Journal of Chemical & Engineering Data. 32 (3): 344–348. doi:10.1021/je00049a018. ISSN 0021-9568.
  4. ^ "Phenyl ether". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b c 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. ISBN 978-3-527-30673-2.
  6. ^ Cook, A. N. (1901). "Derivatives of Phenylether". Journal of the American Chemical Society. 23 (10): 806–813. doi:10.1021/ja02037a005.
  7. ^ 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. ISBN 978-3-527-30673-2.
  8. ^ Ungnade, H. E.; Orwoll, E. F. (1946). "2-Methoxy Diphenyl Ether". Org. Synth. 26: 50. doi:10.15227/orgsyn.026.0050.
  9. ^ 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
  10. ^ "Dowtherm® A 44570".
  11. ^ Suter, C. M.; Maxwell, C. E. (1943). "Phenoxthin". Organic Syntheses.CS1 maint: Multiple names: authors list (link); Collective Volume, 2, p. 485
  12. ^ 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.
  13. ^ DIRECTIVE 2003/11/EC of the European Parliament and of the Council
  14. ^ Sutker, B. J. (2005). Flame Retardants. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_123. ISBN 978-3-527-30673-2.