Diphenyl ether

Last updated
Diphenyl ether
Diphenyl oxide.svg
Diphenyl-ether-from-xtal-2004-CM-3D-ellipsoids.png
Diphenyl ether.jpg
Names
Preferred IUPAC name
1,1′-Oxydibenzene [1]
Systematic IUPAC name
Phenoxybenzene
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-981-2
165477
PubChem CID
RTECS number
  • KN8970000
UNII
UN number 3077
  • InChI=1S/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H Yes check.svgY
    Key: USIUVYZYUHIAEV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
    Key: USIUVYZYUHIAEV-UHFFFAOYAV
  • O(c1ccccc1)c2ccccc2
Properties
C12H10O
Molar mass 170.211 g·mol−1
AppearanceColorless 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 258.55 °C (497.39 °F; 531.70 K) [3] at 100 kPa (1 bar),
121 °C at 1.34 kPa (10.05 mm Hg)
Insoluble
Vapor pressure 0.02 mmHg (25 °C) [2]
-108.1·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H317, H319, H360Fd, H400, H411
P264, P273, P280, P305+P351+P338, P337+P313, P391, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
2
1
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]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 ppm (7 mg/m3) [2]
REL (Recommended)
TWA 1 ppm (7 mg/m3) [2]
IDLH (Immediate danger)
100 ppm [2]
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diphenyl ether is the organic compound with the formula (C 6 H 5)2 O. It is a colorless, low-melting solid. This, the simplest diaryl ether, has a variety of niche applications. [5]

Contents

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 (German : Phenyloxyd) and studied some of its derivatives. [6]

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. [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]

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.

Decabromodiphenyl ether.svg

Related Research Articles

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

<span class="mw-page-title-main">Cumene process</span> Industrial process

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. Haloarenes are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

Polybrominated diphenyl ethers or PBDEs, are a class of organobromine compounds that are used as flame retardants. Like other brominated flame retardants, PBDEs have been used in a wide array of products, including building materials, electronics, furnishings, motor vehicles, airplanes, plastics, polyurethane foams, and textiles. They are structurally akin to polychlorinated diphenyl ethers (PCDEs), polychlorinated biphenyls (PCBs) and other polyhalogenated compounds, consisting of two halogenated aromatic rings. PBDEs are classified according to the average number of bromine atoms in the molecule. The life-saving benefits of fire retardants led to their popularization. Standards for mass transit vehicles continues to increase as of 2021.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

Isobutylene is a hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.

Brominated flame retardants (BFRs) are organobromine compounds that have an inhibitory effect on combustion chemistry and tend to reduce the flammability of products containing them. The brominated variety of commercialized chemical flame retardants comprise approximately 19.7% of the market. They are effective in plastics and textile applications like electronics, clothes, and furniture. 390,000 tons of brominated flame retardants were sold in 2011. This represents 19.7% of the flame retardants market.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

2-Chlorophenol or ortho-chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three isomers of monochlorophenol. Aside from occasional use as a disinfectant, it has few applications. It is an intermediate in the polychlorination of phenol. 2-Chlorophenol is a colorless liquid, although commercial samples are often yellow or amber-colored. It has an unpleasant, penetrating (carbolic) odor. It is poorly soluble in water.

<span class="mw-page-title-main">Epichlorohydrin</span> Chemical compound

Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

<span class="mw-page-title-main">Carbazole</span> Chemical compound

Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole structure, but in which a second benzene ring is fused onto the five-membered ring at the 2–3 position of indole.

<span class="mw-page-title-main">Pentanal</span> Chemical compound

Pentanal is the organic compound with molecular formula C4H9CHO. Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor is described as fermented, bready, fruity, nutty, berry.

Mequinol, MeHQ or 4-methoxyphenol, is an organic compound with the formula CH3OC6H4OH. It is a phenol with a methoxy group in the para position. A colorless solid, it is used in dermatology and organic chemistry.

4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes.

In organic chemistry, transalkylation is a chemical reaction involving the transfer of an alkyl group from one organic compound to another. The reaction is used for the transfer of methyl and ethyl groups between benzene rings. This is of particular value in the petrochemical industry to manufacture p-xylene, styrene, and other aromatic compounds. Motivation for using transalkylation reactions is based on a difference in production and demand for benzene, toluene, and xylenes. Transalkylation can convert toluene, which is overproduced, into benzene and xylene, which are under-produced. Zeolites are often used as catalysts in transalkylation reactions.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

<span class="mw-page-title-main">Isopropenyl acetate</span> Chemical compound

Isopropenyl acetate is an organic compound, which is the acetate ester of the enol tautomer of acetone. This colorless liquid is significant commercially as the principal precursor to acetylacetone. In organic synthesis, it is used to prepare enol acetates of ketones and acetonides from diols.

<span class="mw-page-title-main">Ethyl vinyl ether</span> Chemical compound

Ethyl vinyl ether is an organic compound with the chemical formula CH3CH2OCH=CH2. It is the simplest enol ether that is liquid at room temperature. It is used as a synthetic building block and a monomer.

4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.41.

References

  1. 1 2 3 "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. 1 2 3 4 5 6 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).
  5. 1 2 3 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. ↑ K. List; H. Limpricht (1854). "Ueber das sogenannte Benzoëoxyd und einige andere gepaarte Verbindungen". Annalen der Chemie und Pharmacie (in German). 90 (2): 190–210. doi:10.1002/JLAC.18540900212. ISSN   0075-4617. Wikidata   Q56658706.
  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.
  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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.