Dibenzyl ether

Structural formula
General
Surname	Dibenzyl ether
other names	1,1 ′ - [oxybis (methylene)] bisbenzene; Benzyl ether;
Molecular formula	C 14 H 14 O
Brief description	colorless liquid with a fruity odor
External identifiers / databases
EC number	203-118-2
ECHA InfoCard	100.002.835
PubChem	7657
Wikidata	Q11309584
properties
Molar mass	198.27 g mol −1
Physical state	liquid
density	1.04 g cm −3
Melting point	4 ° C
boiling point	298 ° C
Vapor pressure	approx. 0.1 Pa (25 ° C)
solubility	practically insoluble in water (40 mg l −1 at 35 ° C); miscible with acetone, chloroform, diethyl ether, ethanol;
Refractive index	1.561 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 410
	P: 273
Toxicological data	2500 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

Dibenzyl ether is a chemical compound from the group of diaryl ethers .

Extraction and presentation

Dibenzyl ether can be obtained by reducing benzaldehyde in the presence of dicobalt octacarbonyl . It is also produced as a by-product in the production of benzyl alcohol by hydrolysis of benzyl chloride .

The compound was already represented by Stanislao Cannizzaro by reacting benzyl alcohol with boron trioxide at 120 ° C.

properties

Dibenzyl ether is a flammable, hardly inflammable, colorless liquid with a fruity odor, which is practically insoluble in water. It decomposes when heated. If stored in air for a long time, it also decomposes to benzaldehyde.

use

Dibenzyl ether is used as a plasticizer for nitrocellulose and as a solvent and flavoring agent in perfumery.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on dibenzyl ether in the GESTIS substance database of the IFA , accessed on August 9, 2018(JavaScript required) .
↑ ^a ^b ^c data sheet benzyl ether, 98% from Sigma-Aldrich , accessed on August 9, 2018 ( PDF ).
↑ ^a ^b Entry on dibenzyl ether in the Hazardous Substances Data Bank , accessed on August 9, 2018.
↑ CW Lowe: LXXIII.-dibenzyl ether. In: J. Chem. Soc., Trans. 51, 1887, p. 700, doi : 10.1039 / CT8875100700 .
↑ Frederick G. Eichel, Donald F. Othmer: Benzaldehyde by Autoxidation by Dibenzyl Ether. In: Industrial & Engineering Chemistry. 41, 1949, p. 2623, doi : 10.1021 / ie50479a054 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on dibenzyl ether in the GESTIS substance database of the IFA , accessed on August 9, 2018(JavaScript required) .

[Sigma-2] ta sheet benzyl ether, 98% from Sigma-Aldrich , accessed on August 9, 2018 ( PDF ).

[HSDB-3] Entry on dibenzyl ether in the Hazardous Substances Data Bank , accessed on August 9, 2018.

[DOI10.1039/CT8875100700-4] CW Lowe: LXXIII.-dibenzyl ether. In: J. Chem. Soc., Trans. 51, 1887, p. 700, doi : 10.1039 / CT8875100700 .

[DOI10.1021/ie50479a054-5] Frederick G. Eichel, Donald F. Othmer: Benzaldehyde by Autoxidation by Dibenzyl Ether. In: Industrial & Engineering Chemistry. 41, 1949, p. 2623, doi : 10.1021 / ie50479a054 .