Diphenyl ether

{{Redirect|Phenyl ether|the class of compounds|phenol ether}} {{chembox | Watchedfields = changed | verifiedrevid = 443695188 | ImageFile1 = Diphenyl oxide.svg | ImageSize1 = | ImageClass1 = skin-invert | ImageFile2 = Diphenyl-ether-from-xtal-2004-CM-3D-ellipsoids.png | ImageClass2 = bg-transparent | ImageFile3 = Diphenyl ether.jpg | ImageSize3 = 220px | PIN = 1,1′-Oxydibenzene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 705 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4| chapter = CHAPTER P-6. Applications to Specific Classes of Compounds }}</ref> |SystematicName=Phenoxybenzene | OtherNames = Oxydibenzene Diphenyl ether<ref name=iupac2013/> Diphenyl oxide 1,1′-Oxybisbenzene Phenoxybenzene<ref name=iupac2013/> |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7302 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3O695R5M1U | InChI = 1/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 39258 | SMILES = O(c1ccccc1)c2ccccc2 | InChIKey = USIUVYZYUHIAEV-UHFFFAOYAV | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 38934 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = USIUVYZYUHIAEV-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 101-84-8 | PubChem = 7583 | EC_number = 202-981-2 | RTECS = KN8970000 | UNNumber = 3077 | Gmelin = 165477 | Beilstein = 1364620 }} |Section2={{Chembox Properties | C=12 | H=10 | O=1 | Appearance = Colorless solid or liquid | Odor = geranium-like | MeltingPtC = 25 to 26 | MeltingPt_notes = | BoilingPtC = 258.55 | BoilingPt_notes = at 100 kPa (1 bar), 121 °C at 1.34 kPa (10.05 mm Hg) | BoilingPt_ref = <ref>{{cite journal|last1=Byers|first1=Charles H.|last2=Williams|first2=David F.|date=July 1987|title=Viscosities of pure polyaromatic hydrocarbons|journal=Journal of Chemical & Engineering Data|volume=32|issue=3|pages=344–348|doi=10.1021/je00049a018|issn=0021-9568}}</ref>  | Solubility = Insoluble | VaporPressure = 0.02 mmHg (25 °C)<ref name=PGCH/> | Density = 1.08 g/cm3 (20 °C)<ref name=PGCH/> | MagSus = −108.1·10−6 cm3/mol }} |Section7={{Chembox Hazards | GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|317|319|H360Fd|400|411}} | PPhrases = {{P-phrases|264|273|280|305+351+338|337+313|391|501}} | ExternalSDS = [https://www.sigmaaldrich.com/ES/en/sds/aldrich/w366706?paramid1=3205080 Aldrich MSDS] | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = | NFPA-S = | FlashPtC = 115 | PEL = TWA 1 ppm (7 mg/m3)<ref name=PGCH>{{PGCH|0496}}</ref> | ExploLimits = 0.7%–6.0%<ref name=PGCH/> | IDLH = 100 ppm<ref name=PGCH/> | LD50 = 3370 mg/kg (rat, oral) 4000 mg/kg (rat, oral) 4000 mg/kg (guinea pig, oral)<ref>{{IDLH|101848|Phenyl ether}}</ref> | REL = TWA 1 ppm (7 mg/m3)<ref name=PGCH/> }} | Section8 = {{Chembox Related | OtherCompounds = {{ubl|Diphenyl sulfide|Diphenyl selenide|Diphenyl telluride}} }} }}

'''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.<ref name=Ullmann/>

== 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''' ({{Langx|de|Phenyloxyd}}) and studied some of its derivatives.<ref>{{Cite Q|Q56658706}}</ref>

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.<ref>{{cite book |author1=Fahlbusch, K.-G. |author2=Hammerschmidt, F.-J. |author3=Panten, J. |author4=Pickenhagen, W. |author5=Schatkowski, D. |author6=Bauer, K. |author7=Garbe, D. |author8=Surburg, H. | chapter = Flavor and Fragrances | title = Ullmann's Encyclopedia of Industrial Chemistry | pages = | year = 2003 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a11_141 | isbn = 978-3-527-30673-2 }}</ref>

Related compounds are prepared by Ullmann reactions.<ref>{{cite journal|journal=Org. Synth. |author1= Ungnade, H. E. |author2=Orwoll, E. F. | title = 2-Methoxy Diphenyl Ether | volume = 26 | pages = 50 | year = 1946 | doi= 10.15227/orgsyn.026.0050}}</ref>

The compound undergoes reactions typical of other phenyl rings, including hydroxylation, nitration, halogenation, sulfonation, and Friedel–Crafts alkylation or acylation.<ref name=Ullmann>{{Ullmann|author1=Fiege, H. |author2=Voges, H.-M. |author3=Hamamoto, T |author4=Umemura, S. |author5=Iwata, T. |author6=Miki, H. |author7=Fujita, Y. |author8=Buysch, H.-J. |author9=Garbe, D. |author10=Paulus, W. | title = Phenol Derivatives | year = 2000 | doi = 10.1002/14356007.a19_313}}</ref>

== 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.<ref>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</ref><ref>{{cite web | url=http://www.sigmaaldrich.com/catalog/product/aldrich/44570 | title=Dowtherm® A 44570}}</ref>

Diphenyl ether is a starting material in the production of phenoxathiin via the Ferrario reaction.<ref>{{OrgSynth | author = Suter, C. M. | author2 = Maxwell, C. E. | title = Phenoxthin | journal = Organic Syntheses | collvol = 2 | issue = | collvolpages = 485 | year = 1943 | prep = cv2p0485}}</ref> Phenoxathiin is used in polyamide and polyimide production.<ref>{{cite journal |author1=Mitsuru Ueoda |author2=Tatsuo Aizawa |author3=Yoshio Imai | title = Preparation and properties of polyamides and polyimides containing phenoxathiin units | journal = Journal of Polymer Science: Polymer Chemistry Edition | volume = 15 | issue = 11 | pages = 2739–2747 | year = 1977 | doi =10.1002/pol.1977.170151119 |bibcode=1977JPoSA..15.2739U }}</ref>

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.<ref name=Ullmann/>

==Related compounds== 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.<ref name="EU-Ban">[http://eur-lex.europa.eu/LexUriServ/site/en/oj/2003/l_042/l_04220030215en00450046.pdf DIRECTIVE 2003/11/EC of the European Parliament and of the Council]</ref> DecaBDE, also known as decabromodiphenyl oxide,<ref>{{cite book | author = Sutker, B. J. | chapter = Flame Retardants | title = Ullmann's Encyclopedia of Industrial Chemistry | pages = | year = 2005 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a11_123 | isbn = 978-3-527-30673-2 }}</ref> 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== {{Reflist}}

{{DEFAULTSORT:Diphenyl ether}} Category:Diphenyl ethers Category:Symmetrical ethers Category:Sweet-smelling chemicals