Diphenyl ether

Diphenyl ether
Names
	Preferred IUPAC name 1,1′-Oxydibenzene
	Systematic IUPAC name Phenoxybenzene
	Other names Oxydibenzene; Diphenyl ether; Diphenyl oxide; 1,1′-Oxybisbenzene; Phenoxybenzene
Identifiers
CAS Number	101-84-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1364620
ChEBI	CHEBI:39258 ;
ChEMBL	ChEMBL38934 ;
ChemSpider	7302 ;
ECHA InfoCard	100.002.711
EC Number	202-981-2;
Gmelin Reference	165477
PubChem CID	7583;
RTECS number	KN8970000;
UNII	3O695R5M1U ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID9021847 ;
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Properties
Chemical formula	C12H10O
Molar mass	170.211 g·mol−1
Appearance	Colorless solid or liquid
Odor	geranium-like
Density	1.08 g/cm3 (20 °C)
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) at 100 kPa (1 bar),; 121 °C at 1.34 kPa (10.05 mm Hg)
Solubility in water	Insoluble
Vapor pressure	0.02 mmHg (25 °C)
Magnetic susceptibility (χ)	-108.1·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H319, H360Fd, H400, H411
Precautionary statements	P264, P273, P280, P305+P351+P338, P337+P313, P391, P501
NFPA 704 (fire diamond)	2 1
Flash point	115 °C (239 °F; 388 K)
Explosive limits	0.7%–6.0%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3370 mg/kg (rat, oral); 4000 mg/kg (rat, oral); 4000 mg/kg (guinea pig, oral)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 1 ppm (7 mg/m3)
REL (Recommended)	TWA 1 ppm (7 mg/m3)
IDLH (Immediate danger)	100 ppm
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). verify (what is ?) Infobox references

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]

Synthesis and reactions

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:

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]

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.^[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.

References

^ Jump up to: ^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.
^ Jump up to: ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0496". National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ "Phenyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Jump up to: ^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 978-3527306732.
^ Cook, A. N. (1901). "Derivatives of Phenylether". Journal of the American Chemical Society. 23 (10): 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. ISBN 978-3-527-30673-2.
^ Ungnade, H. E.; Orwoll, E. F. (1946). "2-Methoxy Diphenyl Ether". Org. Synth. 26: 50. doi:10.15227/orgsyn.026.0050.
^ 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
^ "Dowtherm^® A 44570".
^ Suter, C. M.; Maxwell, C. E. (1943). "Phenoxthin". Organic Syntheses; Collected Volumes, vol. 2, p. 485.
^ 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.
^ 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. ISBN 978-3-527-30673-2.

[iupac2013-1] Jump up to: ^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.

[PGCH-2] Jump up to: ^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 or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-5] Jump up to: ^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 978-3527306732.

[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; Collected Volumes, vol. 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.

[EU-Ban-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.

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