Chemical Properties
Phenyl glycidyl ether, also known as glycidyl phenyl ether or PGE, is a clear liquid with a sweet odor that is considered unpleasant. It is soluble in ether and benzene, but insoluble in water. It has the ability to volatilize with water vapor. It is used in the production of epoxy resins, as a chemical intermediate, and as a stabilizer.
Uses
Phenyl glycidyl ether (PGE) is utilized in organic syntheses as an intermediate. As a reactive diluent, PGE is incorporated into uncured epoxy resins to lower viscosity, thereby facilitating casting, adhesives, and laminating applications.
Uses
2-Phenylglycidyl ether is an organic synthesis; chemical intermediate with high solvency for halogenated materials; reactive diluent of epoxy-resin systems; forms chemical bonds with the resin during cure and accelerates the curing process.
Production Methods
PGE is synthesized by condensation of phenol with epichlorohydrin,
with subsequent dehydrochlorination with caustic
to form the epoxy ring.
Definition
ChEBI: Phenyl glycidyl ether is an aromatic ether.
Synthesis Reference(s)
The Journal of Organic Chemistry, 50, p. 1784, 1985
DOI: 10.1021/jo00210a053
General Description
Colorless liquid.
Air & Water Reactions
Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Slightly soluble in water.
Reactivity Profile
Glycidyl phenyl ether, an ether, can act as a base. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
Health Hazard
PGE is a toxic compound exhibiting moderate irritant action and carcinogenicity inanimals. Application of 0.25 mg resulted insevere eye irritation in rabbits, while 500 mgcaused moderate skin irritation over a periodof 24 hours. Prolonged or repeated contactcan cause moderate irritation and skin sensitization in humans.
The symptoms of its toxicity in animalswere depression of the central nervous system and paralysis of the respiratory tract.Prolonged exposure caused changes in thekidney, liver, thymus, and testes, and lossof hair in rats. The toxicity of this compound in humans is low and the health hazardcan arise primarily from its skin-sensitizationaction.
LD50 value, oral (mice): 1400 mg/kg
DGE showed carcinogenicity in rats, causingnasal cancer.
Fire Hazard
Glycidyl phenyl ether is probably combustible.
Contact allergens
This monoglycidyl derivative is a reactive diluent in
epoxy resins Bisphenol A type. It is a component of
epoxy paints, epoxy glues, and epoxy resins.
Sensitization has been observed in many professions,
such as in construction workers, marble workers,
ceramic workers, and shoemakers.
Safety Profile
Confirmed carcinogen with experimental carcinogenic data. Moderately toxic by ingestion, skin contact, and subcutaneous routes. A severe eye and skin irritant. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Used as a chemical intermediate. See also ETHERS
Potential Exposure
PGE is used to increase storage time and stability of halogenated compounds; as a reactive diluent in uncured epoxy resins to reduce the viscosity of the uncured system for ease in casting; adhesive, and laminating applications. NIOSH once estimated that 8000 workers are potentially exposed to PGE.
Carcinogenicity
Chronic exposure of rats to 1 or 12ppm
6 hours/day, 5 days/week for 2 years caused an
increased incidence of rhinitis, squamous metaplasia,
and epidermal carcinomas of the nasal
cavity.4 The IARC has determined that there is
sufficient evidence for the carcinogenicity of
PGE in animals and that it is possibly carcinogenic
to humans.
Shipping
UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, amines, and curing agents. PGE can presumably form explosive peroxides
Waste Disposal
Concentrated waste containing no peroxides-discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxidesperforation of a container of the waste from a safe distance followed by open burning.
