# Diphenyl ether

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> Source: https://en.wikipedia.org/wiki/Diphenyl_ether
> Source revision: 1353132375
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{{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](/source/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<br />Diphenyl ether<ref name=iupac2013/><br />Diphenyl oxide<br />1,1′-Oxybisbenzene<br />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](/source/geranium)-like
| MeltingPtC = 25 to 26
| MeltingPt_notes = 
| BoilingPtC = 258.55
| BoilingPt_notes = at 100 kPa (1 bar),<br/>121&nbsp;°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> <!-- given in the reference as 531.7 K -->
| Solubility = Insoluble
| VaporPressure = 0.02 mmHg (25 °C)<ref name=PGCH/>
| Density = 1.08 g/cm<sup>3</sup> (20 °C)<ref name=PGCH/>
| MagSus = −108.1·10<sup>−6</sup> cm<sup>3</sup>/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/m<sup>3</sup>)<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)<br/>4000 mg/kg (rat, oral)<br/>4000 mg/kg (guinea pig, oral)<ref>{{IDLH|101848|Phenyl ether}}</ref>
| REL = TWA 1 ppm (7 mg/m<sup>3</sup>)<ref name=PGCH/> 
  }}
| Section8 = {{Chembox Related
| OtherCompounds = {{ubl|[Diphenyl sulfide](/source/Diphenyl_sulfide)|[Diphenyl selenide](/source/Diphenyl_selenide)|[Diphenyl telluride](/source/Diphenyl_telluride)}}
  }}
}}

'''Diphenyl ether''' is the [organic compound](/source/organic_compound) with the formula ([C](/source/carbon)<sub>6</sub>[H](/source/hydrogen)<sub>5</sub>)<sub>2</sub>[O](/source/oxygen). It is a colorless, low-melting solid.  This compound, the simplest diaryl [ether](/source/ether), has a variety of niche applications.<ref name=Ullmann/>

== Synthesis and reactions==
Diphenyl ether was discovered by [Heinrich Limpricht](/source/Heinrich_Limpricht) and Karl List in 1855, when they reproduced Carl Ettling's [destructive distillation](/source/destructive_distillation) of [copper benzoate](/source/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](/source/Williamson_ether_synthesis), here the reaction of [phenol](/source/phenol) and [bromobenzene](/source/bromobenzene) in the presence of [base](/source/Base_(chemistry)) and a [catalytic](/source/catalysis) amount of [copper](/source/copper):
:PhOH  +  PhBr  →  PhOPh  +  HBr
Involving similar reactions, diphenyl ether is a significant side product in the high-pressure [hydrolysis](/source/hydrolysis) of [chlorobenzene](/source/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 reaction](/source/Ullmann_reaction)s.<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](/source/phenyl) rings, including [hydroxylation](/source/hydroxylation), [nitration](/source/nitration), [halogenation](/source/halogenation), [sulfonation](/source/sulfonation), and [Friedel–Crafts alkylation or acylation](/source/Friedel%E2%80%93Crafts_reaction).<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](/source/eutectic) mixture with [biphenyl](/source/biphenyl), used as a [heat transfer fluid](/source/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<SUP>®</SUP> A 44570}}</ref>

Diphenyl ether is a starting material in the production of [phenoxathiin](/source/phenoxathiin) via the [Ferrario reaction](/source/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](/source/polyamide) and [polyimide](/source/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](/source/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 [polyester](/source/polyester)s.<ref name=Ullmann/>

==Related compounds==
Several [polybrominated diphenyl ethers](/source/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}}

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

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Adapted from the Wikipedia article [Diphenyl ether](https://en.wikipedia.org/wiki/Diphenyl_ether) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Diphenyl_ether?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.