Chemical Properties
Dibenzyl ether has a slightly earthy, mushroom-like odor with a rosy undertone.
Chemical Properties
Dibenzyl ether is a clear, almost colorless liquid. It is miscible with alcohols and ethers, but insoluble in water. Dibenzyl ether is used as special solvent and delustering agent for textiles.
Uses
Benzyl ether is used as an effective GFP friendly tissue clearing medium for mouse brains. It is also used in a study to develop a detailed protocol for performing 3D imaging of solvent-cleared organs and its application to various microscopy techniques. It is also employed as a plasticizer for nitrocellulose and synthetic rubber, a solvent in perfumery, and a flavoring agent in chewing gums and baked goods. It can also be used as a plasticizer for nitrocellulose and a solvent in spices.
Application
Benzyl ether is an aromatic ether that is commonly employed as a protecting agent and benzylating agent. It is a plasticizer for nitrocellulose and a solvent in perfumery.
Definition
ChEBI: Dibenzyl ether is a benzyl ether in which the oxygen atom is connected to two benzyl groups. It has a role as a metabolite.
Preparation
As a by-product in the preparation of benzyl alcohol by hydrolysis of benzyl chloride; by using a concentrated caustic
instead of carbonate, yields can be improved to 50% or higher.
General Description
Colorless liquid with a mild odor.
Air & Water Reactions
Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Insoluble in water.
Reactivity Profile
Benzyl ether can act as a base to form salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. Burns readily but relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond.
Hazard
Moderately toxic by ingestion. A skin irri-
tant.
Health Hazard
Inhalation may cause nausea because of disagreeable odor. Contact of liquid with eyes causes mild irritation. Prolonged exposure of skin to liquid causes reddening and irritation. Ingestion produces nausea.
Fire Hazard
Benzyl ether is combustible.
Synthesis
Benzyl ether is formed when benzyl alcohol is heated with strong acids or bases. It is produced almost exclusively by the alkaline hydrolysis of benzyl chloride. Heat treatment decomposes dibenzyl ether into benzaldehyde and toluene.
Purification Methods
Reflux the ether over sodium, then distil it under reduced pressure. It been purified by fractional freezing. [Beilstein 6 IV 2240.]
