diphenyl ether
{{chembox
| Watchedfields = changed
| verifiedrevid = 443695188
| ImageFile1 = Diphenyl oxide.svg
| ImageSize1 =
| ImageFile2 = Diphenyl-ether-from-xtal-2004-CM-3D-ellipsoids.png
| ImageFile3 = Diphenyl ether.jpg
| ImageSize3 = 220px
| PIN = 1,1′-Oxydibenzene{{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 }}
|SystematicName=Phenoxybenzene
| OtherNames = Oxydibenzene
Diphenyl ether
Diphenyl oxide
1,1′-Oxybisbenzene
Phenoxybenzene
|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)
| Solubility = Insoluble
| VaporPressure = 0.02 mmHg (25 °C)
| Density = 1.08 g/cm3 (20 °C)
| 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){{PGCH|0496}}
| LD50 = 3370 mg/kg (rat, oral)
4000 mg/kg (rat, oral)
4000 mg/kg (guinea pig, oral){{IDLH|101848|Phenyl ether}}
}}
}}
{{Redirect|Phenyl ether|the class of compounds|phenol ether}}
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.
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.{{Cite Q|Q56658706}}
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.{{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 }}
Related compounds are prepared by Ullmann reactions.{{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}}
The compound undergoes reactions typical of other phenyl rings, including hydroxylation, nitration, halogenation, sulfonation, and Friedel–Crafts alkylation or acylation.{{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}}
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.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{{cite web | url=http://www.sigmaaldrich.com/catalog/product/aldrich/44570 | title=Dowtherm® A 44570}}
Diphenyl ether is a starting material in the production of phenoxathiin via the Ferrario reaction.{{OrgSynth
| author = Suter, C. M.
| author2 = Maxwell, C. E.
| title = Phenoxthin
| journal = Organic Syntheses
| collvol = 2
| issue =
| collvolpages = 485
| year = 1943
| prep = cv2p0485}} Phenoxathiin is used in polyamide and polyimide production.{{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 }}
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.
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.[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] DecaBDE, also known as decabromodiphenyl oxide,{{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 }} 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
{{Reflist}}
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{{DEFAULTSORT:Diphenyl ether}}