Diphenyl ether

Structural formula
General
Surname	Diphenyl ether
other names	Phenyl ether; Diphenyl oxide; Phenoxybenzene; Phenoxybenzene ( IUPAC ); 1,1'-oxybisbenzene;
Molecular formula	C 12 H 10 O
Brief description	colorless, flammable solid with a geranium-like odor
External identifiers / databases
EC number	202-981-2
ECHA InfoCard	100.002.711
PubChem	7583
Wikidata	Q419453
properties
Molar mass	170.21 g mol −1
Physical state	firmly
density	1.07 g cm −3
Melting point	27 ° C
boiling point	258 ° C; 259 ° C;
Vapor pressure	8 Pa (20 ° C)
solubility	almost insoluble in water (21 mg l −1 at 20 ° C)
Refractive index	1.579 (20 ° C)
safety instructions
H and P phrases	H: 319-411
	P: 280-273-264-305 + 351 + 338-337 + 313-501
MAK	1 ml m −3 or 7.1 mg m −3
Toxicological data	2450 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Diphenylether is a chemical compound from the group of ethers and the simplest diarylether . The compound consists of two benzene rings linked by an oxygen atom .

Extraction and presentation

Diphenyl ether and many of its properties were first published in early 1901. It is represented by a Ullmann condensation , through the reaction of phenol and bromobenzene in the presence of a base and a catalyst such as copper :

{\ displaystyle \ mathrm {PhONa + PhBr \ rightarrow PhOPh + NaBr}}

Due to side reactions, diphenyl ether is also a significant by-product in the high pressure hydrolysis of chlorobenzene in the production of phenol.

use

Diphenyl ether is used as a rose perfume for soaps and detergents and as a heat transfer medium. It is the starting material for many derived compounds and chemical syntheses. For example, its brominated derivatives ( polybrominated diphenyl ethers ) are used as flame retardants in many plastics and textiles. The aminofen derivative is used to produce diphenyl ether herbicides .

A eutectic mixture of biphenyl and diphenyl ether is offered as a heat transfer oil under the trade names Dowtherm A and Therminol VP-1 .

safety instructions

Diphenyl ether forms flammable vapor-air mixtures at high temperatures. With a flash point of 115 ° C, the substance is considered to be hardly inflammable. The explosion range is between 0.8% by volume (55 g / m ³ ) as the lower explosion limit (LEL) and 15% by volume (1060 g / m ³ ) as the upper explosion limit (UEL). The ignition temperature is 610 ° C. The substance therefore falls into temperature class T1.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on diphenyl ether in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
^ Siegfried Hauptmann : Organic Chemistry , 2nd revised edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, p. 340, ISBN 3-342-00280-8 .
↑ Data sheet Diphenyl ether at AlfaAesar, accessed on June 25, 2016 ( PDF )(JavaScript required) .
↑ ^a ^b data sheet Diphenyl ether from Sigma-Aldrich , accessed on June 25, 2016 ( PDF ).
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 101-84-8 or diphenyl ether ), accessed on November 2, 2015.
^ Cook, AN: Derivatives of Phenylether . In: Journal of the American Chemical Society . 23, No. 11, 1901, pp. 806-813. doi : 10.1021 / ja02037a005 .
↑ Kürti; Czakó, Strategic Applications of Named Reactions in Organic Synthesis , 2005, p. 464.
↑ Fahlbusch, K.-G .; Hammerschmidt, F.-J .; Panten, J .; Pickenhagen, W .; Schatkowski, D .; Bauer, K .; Garbe, D .; Surburg, H .: Flavor and Fragrances . In: Wiley-VCH (Ed.): Ullmann's Encyclopedia of Industrial Chemistry . , Weinheim 2003. doi : 10.1002 / 14356007.a11_141 .
↑ DOWTHERM Synthetic Organic Fluids
↑ Therminol VP-1 Heat Transfer Fluid
^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on diphenyl ether in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[Hauptmann1-2] Siegfried Hauptmann : Organic Chemistry , 2nd revised edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, p. 340, ISBN 3-342-00280-8 .

[Alfa-3] Data sheet Diphenyl ether at AlfaAesar, accessed on June 25, 2016 ( PDF )(JavaScript required) .

[Sigma-4] ta sheet Diphenyl ether from Sigma-Aldrich , accessed on June 25, 2016 ( PDF ).

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 101-84-8 or diphenyl ether ), accessed on November 2, 2015.

[6] Cook, AN: Derivatives of Phenylether . In: Journal of the American Chemical Society . 23, No. 11, 1901, pp. 806-813. doi : 10.1021 / ja02037a005 .

[7] Kürti; Czakó, Strategic Applications of Named Reactions in Organic Synthesis , 2005, p. 464.

[8] Fahlbusch, K.-G .; Hammerschmidt, F.-J .; Panten, J .; Pickenhagen, W .; Schatkowski, D .; Bauer, K .; Garbe, D .; Surburg, H .: Flavor and Fragrances . In: Wiley-VCH (Ed.): Ullmann's Encyclopedia of Industrial Chemistry . , Weinheim 2003. doi : 10.1002 / 14356007.a11_141 .

[9] DOWTHERM Synthetic Organic Fluids

[10] Therminol VP-1 Heat Transfer Fluid

[Brandes-11] E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.